There Are Several Families of Hydrocarbons Among Which Are Alkanes

Affiliate xx. Organic Chemistry

20.ane Hydrocarbons

Learning Objectives

By the stop of this department, you will be able to:

  • Explain the importance of hydrocarbons and the reason for their diversity
  • Name saturated and unsaturated hydrocarbons, and molecules derived from them
  • Describe the reactions feature of saturated and unsaturated hydrocarbons
  • Identify structural and geometric isomers of hydrocarbons

The largest database[i] of organic compounds lists about 10 million substances, which include compounds originating from living organisms and those synthesized past chemists. The number of potential organic compounds has been estimated[2] at ten60—an astronomically high number. The beingness of so many organic molecules is a event of the ability of carbon atoms to course upwards to four strong bonds to other carbon atoms, resulting in chains and rings of many different sizes, shapes, and complexities.

The simplest organic compounds contain only the elements carbon and hydrogen, and are chosen hydrocarbons. Fifty-fifty though they are equanimous of merely ii types of atoms, in that location is a wide diverseness of hydrocarbons because they may consist of varying lengths of chains, branched chains, and rings of carbon atoms, or combinations of these structures. In addition, hydrocarbons may differ in the types of carbon-carbon bonds nowadays in their molecules. Many hydrocarbons are found in plants, animals, and their fossils; other hydrocarbons accept been prepared in the laboratory. We use hydrocarbons every day, mainly equally fuels, such as natural gas, acetylene, propane, butane, and the principal components of gasoline, diesel fuel, and heating oil. The familiar plastics polyethylene, polypropylene, and polystyrene are also hydrocarbons. We can distinguish several types of hydrocarbons by differences in the bonding between carbon atoms. This leads to differences in geometries and in the hybridization of the carbon orbitals.

Alkanes

Alkanes, or saturated hydrocarbons, contain merely single covalent bonds betwixt carbon atoms. Each of the carbon atoms in an alkane series has sp three hybrid orbitals and is bonded to 4 other atoms, each of which is either carbon or hydrogen. The Lewis structures and models of marsh gas, ethane, and pentane are illustrated in Figure ane. Carbon bondage are normally fatigued as directly lines in Lewis structures, but ane has to remember that Lewis structures are not intended to indicate the geometry of molecules. Notice that the carbon atoms in the structural models (the ball-and-stick and space-filling models) of the pentane molecule do not prevarication in a direct line. Considering of the sp iii hybridization, the bond angles in carbon bondage are close to 109.five°, giving such chains in an alkane a zigzag shape.

The structures of alkanes and other organic molecules may also exist represented in a less detailed fashion by condensed structural formulas (or only, condensed formulas). Instead of the usual format for chemical formulas in which each chemical element symbol appears just once, a condensed formula is written to propose the bonding in the molecule. These formulas have the advent of a Lewis structure from which about or all of the bail symbols have been removed. Condensed structural formulas for ethane and pentane are shown at the lesser of Figure 1, and several boosted examples are provided in the exercises at the end of this affiliate.

The figure illustrates four ways to represent molecules for molecules of methane, ethane, and pentane. In the first row of the figure, Lewis structural formulas show element symbols and bonds between atoms. Methane has a central C atom with four H atoms bonded to it. Ethane has a C atom with three H atoms bonded to it. The C atom is also bonded to another C atom with three H atoms bonded to it. Pentane has a C atom with three H atoms bonded to it. The C atom is bonded to another C atom with two H atoms bonded to it. The C atom is bonded to another C atom with two H atoms bonded to it. The C atom is bonded to another C atom with two H atoms bonded to it. The C atom is bonded to another C atom with three H atoms bonded to it. In the second row, ball-and-stick models are shown. In these representations, bonds are represented with sticks, and elements are represented with balls. Carbon atoms are black and hydrogen atoms are white in this image. In the third row, space-filling models are shown. In these models, atoms are enlarged and pushed together, without sticks to represent bonds. The molecule names and structural formulas are provided in the fourth row. Methane is named and represented with a condensed structural formula as C H subscript 4. Ethane is named and represented with two structural formulas C H subscript 3 C H subscript 3 and C subscript 2 H subscript 6. Pentane is named and represented as both C H subscript 3 C H subscript 2 C H subscript 2 C H subscript 2 C H subscript 3 and C subscript 5 H subscript 12.
Figure 1. Pictured are the Lewis structures, ball-and-stick models, and infinite-filling models for molecules of methyl hydride, ethane, and pentane.

A mutual method used by organic chemists to simplify the drawings of larger molecules is to employ a skeletal structure (as well called a line-angle structure). In this blazon of structure, carbon atoms are not symbolized with a C, but represented past each cease of a line or curve in a line. Hydrogen atoms are non fatigued if they are attached to a carbon. Other atoms besides carbon and hydrogen are represented by their elemental symbols. Figure 2 shows three different ways to draw the same structure.

In this figure, a hydrocarbon molecule is shown in three ways. First, an expanded formula shows all individual carbon atoms, hydrogen atoms, and bonds in a branched hydrocarbon molecule. An initial C atom is bonded to three H atoms. The C atom is bonded to another C atom in the chain. This second C atom is bonded to one H atom and another C atom above the chain. The C atom bonded above the second C atom in the chain is bonded to three H atoms. The second C atom in the chain is bonded to a third C atom in the chain. This third C atom is bonded to on H atom and another C atom below the chain. This C atom is bonded to two H atoms and another C atom below the chain. This second C atom below the chain is bonded to three H atoms. The third C atom in the chain is bonded to a fourth C atom in the chain. The fourth C atom is bonded to two H atoms and a fifth C atom. The fifth C atom is bonded to two H atoms and a sixth C atom. The sixth C atom is bonded to three H atoms. Second, a condensed formula shows each carbon atom of the molecule in clusters with the hydrogen atoms bonded to it, leaving C H, C H subscript 2, and C H subscript 3 groups with bonds between them. The structure shows a C H subscript 3 group bonded to a C H group. The C H group is bonded above to a C H subscript 3 group. The C H group is also bonded to another C H group. This C H group is bonded to a C H subscript 2 group below and a C H subscript 3 group below that. This C H group is also bonded to a C H subscript 2 group which is bonded to another C H subscript 2 group. This C H subscript 2 group is bonded to a final C H subscript 2 group. The final structure in the figure is a skeletal structure which includes only line segments arranged to indicate the structure of the molecule.
Figure 2. The same structure can be represented iii dissimilar ways: an expanded formula, a condensed formula, and a skeletal structure.

Case 1

Drawing Skeletal Structures
Describe the skeletal structures for these two molecules:
Figure a shows a branched molecule with C H subscript 3 bonded to C with C H subscript 3 groups bonded both above and below it. To the right of the central C, a C H is bonded which has a C H subscript 3 group bonded above and to the right and below and to the right. Figure b shows a straight chain molecule composed of C H subscript 3 C H subscript 2 C H subscript 2 C H subscript 2 C H subscript 2 C H subscript 2 C H subscript 3.

Solution
Each carbon cantlet is converted into the end of a line or the place where lines intersect. All hydrogen atoms attached to the carbon atoms are left out of the structure (although we even so need to recognize they are at that place):
Figure a shows a branched skeleton structure that looks like a plus sign with line segments extending up and to the right and down and to the left of the rightmost point of the plus sign. Figure b appears in a zig zag pattern made with six line segments. The segments rise, fall, rise, fall, rise, and fall moving left to right across the figure.

Cheque Your Learning
Describe the skeletal structures for these two molecules:
Figure a shows five C H subscript 2 groups and one C H group bonded in a hexagonal ring. A C H subscript 3 group appears above and to the right of the ring, bonded to the ring on the C H group appearing at the upper right portion of the ring. In b, a straight chain molecule composed of C H subscript 3 C H subscript 2 C H subscript 2 C H subscript 2 C H subscript 3 is shown.

Answer:
In a, a hexagon with a vertex at the top is shown. The vertex just to the right has a line segment attached that extends up and to the right. In b, a zig zag pattern is shown in which line segments rise, fall, rise, fall, and rise moving left to right.

Example 2

Interpreting Skeletal Structures
Identify the chemical formula of the molecule represented here:
This figure shows a pentagon with a vertex pointing right, from which a line segment extends that has two line segments attached at its right end, one extending up and to the right, and the other extending down and to the right.

Solution
There are 8 places where lines intersect or end, meaning that there are 8 carbon atoms in the molecule. Since we know that carbon atoms tend to make four bonds, each carbon cantlet will have the number of hydrogen atoms that are required for 4 bonds. This compound contains 16 hydrogen atoms for a molecular formula of CeightH16.

Location of the hydrogen atoms:
In this figure a ring composed of four C H subscript 2 groups and one C H group in a pentagonal shape is shown. From the C H group, which is at the right side of the pentagon, a C H is bonded. From this C H, a C H subscript 3 group is bonded above and to the right and a second is bonded below and to the right.

Check Your Learning
Identify the chemical formula of the molecule represented here:
A skeleton model is shown with a zig zag pattern that rises, falls, rises, and falls again left to right through the center of the molecule. From the two risen points, line segments extend both up and down, creating four branches.

All alkanes are equanimous of carbon and hydrogen atoms, and have similar bonds, structures, and formulas; noncyclic alkanes all take a formula of CnH2n+2. The number of carbon atoms present in an paraffin has no limit. Greater numbers of atoms in the molecules will lead to stronger intermolecular attractions (dispersion forces) and correspondingly different physical properties of the molecules. Properties such as melting betoken and humid point (Table ane) usually alter smoothly and predictably as the number of carbon and hydrogen atoms in the molecules change.

Alkane Molecular Formula Melting Point (°C) Humid Betoken (°C) Phase at STP[iii] Number of Structural Isomers
marsh gas CH4 –182.5 –161.v gas ane
ethane C2H6 –183.three –88.6 gas one
propane C3Height –187.7 –42.1 gas i
butane CivH10 –138.iii –0.5 gas two
pentane C5H12 –129.seven 36.1 liquid 3
hexane C6H14 –95.three 68.7 liquid five
heptane CviiH16 –ninety.6 98.4 liquid nine
octane C8H18 –56.viii 125.7 liquid 18
nonane C9H20 –53.6 150.8 liquid 35
decane C10H22 –29.7 174.0 liquid 75
tetradecane C14Hxxx five.9 253.five solid 1858
octadecane C18H38 28.two 316.1 solid 60,523
Table 1. Properties of Some Alkanes[4]

Hydrocarbons with the aforementioned formula, including alkanes, can have unlike structures. For example, two alkanes have the formula CfourH10: They are chosen n-butane and 2-methylpropane (or isobutane), and have the post-obit Lewis structures:


The figure illustrates three ways to represent molecules of n dash butane and 2 dash methlylpropane. In the first row of the figure, Lewis structural formulas show element symbols and bonds between atoms. The n dash butane molecule shows 4 carbon atoms represented by the letter C bonded in a straight horizontal chain with hydrogen atoms represented by the letter H bonded above and below all carbon atoms. H atoms are bonded at the ends to the left and right of the left-most and right-most C atoms. In the second row, ball-and-stick models are shown. In these representations, bonds are represented with sticks, and elements are represented with balls. Carbon atoms are black and hydrogen atoms are white in this image. In the third row, space-filling models are shown. In these models, atoms are enlarged and pushed together, without sticks to represent bonds. The molecule names are provided in the fourth row.

The compounds n-butane and 2-methylpropane are structural isomers (the term constitutional isomers is besides commonly used). Constitutional isomers have the aforementioned molecular formula but different spatial arrangements of the atoms in their molecules. The n-butane molecule contains an unbranched concatenation, meaning that no carbon atom is bonded to more than 2 other carbon atoms. We employ the term normal, or the prefix n, to refer to a chain of carbon atoms without branching. The compound ii–methylpropane has a branched chain (the carbon atom in the center of the Lewis structure is bonded to three other carbon atoms)

Identifying isomers from Lewis structures is not every bit like shooting fish in a barrel every bit it looks. Lewis structures that look different may actually correspond the same isomers. For example, the iii structures in Figure 3 all represent the aforementioned molecule, due north-butane, and hence are non different isomers. They are identical because each contains an unbranched chain of iv carbon atoms.

The figure illustrates three ways to represent molecules of n dash butane. In the first row of the figure, Lewis structural formulas show carbon and hydrogen element symbols and bonds between the atoms. The first structure in this row shows three of the linked C atoms in a horizontal row with a single C atom bonded above the left-most carbon. The left-most C atom has two H atoms bonded to it. The C atom bonded above the left-most C atom has three H atoms bonded to it. The C atom bonded to the right of the left-most C atom has two H atoms bonded to it. The right-most C atom has three H atoms bonded to it. The C atoms and the bonds connecting all the C atoms are red. The second structure in the row similarly shows the row of three linked C atoms with a single C atom bonded below the C atom to the left. The left-most C atom has two H atoms bonded to it. The C atom bonded below the left-most C atom has three H atoms bonded to it. The C atom bonded to the right of the left-most C atom has two H atoms bonded to it. The right-most atom has three H atoms bonded to it. All the C atoms and the bonds between them are red. The third structure has two C atoms bonded in a row with a third C atom bonded above the left C atom and the fourth C atom bonded below the right C atom. The C atom bonded above the left C atom has three H atoms bonded to it. The left C atom has two H atoms bonded to it. The right C atom has two H atoms bonded to it. The C atom bonded below the right C atom has three H atoms bonded to it. All the C atoms and the bonds between them are red. In the second row, ball-and-stick models for the structures are shown. In these representations, bonds are represented with sticks, and elements are represented with balls. Carbon atoms are black and hydrogen atoms are white in this image. In the third row, space-filling models are shown. In these models, atoms are enlarged and pushed together, without sticks to represent bonds.
Figure 3. These three representations of the construction of n-butane are not isomers because they all contain the same organization of atoms and bonds.

The Basics of Organic Classification: Naming Alkanes

The International Union of Pure and Applied Chemistry (IUPAC) has devised a system of nomenclature that begins with the names of the alkanes and can exist adjusted from at that place to account for more complicated structures. The nomenclature for alkanes is based on 2 rules:

  1. To proper noun an alkane, first identify the longest chain of carbon atoms in its construction. A two-carbon chain is chosen ethane; a three-carbon chain, propane; and a 4-carbon concatenation, butane. Longer chains are named as follows: pentane (five-carbon chain), hexane (half dozen), heptane (seven), octane (8), nonane (ix), and decane (x). These prefixes tin be seen in the names of the alkanes described in Table 1.
  2. Add prefixes to the name of the longest chain to indicate the positions and names of substituents. Substituents are branches or functional groups that supersede hydrogen atoms on a chain. The position of a substituent or branch is identified by the number of the carbon atom it is bonded to in the chain. Nosotros number the carbon atoms in the chain past counting from the stop of the chain nearest the substituents. Multiple substituents are named individually and placed in alphabetical order at the front of the proper noun.

This figure shows structural formulas for propane, 2 dash chloropropane, 2 dash methylpropane, 2 comma 4 dash difluorohexane, and 1 dash bromo dash 3 dash chlorohexane. In each of the structures, the carbon atoms are in a row with bonded halogen atoms and a methyl group bonded below the figures. Propane is listed as simply C H subscript 3 C H subscript 2 C H subscript 3, with the numbers 1, 2, and 3 appearing above the carbon atoms from left to right. 2 dash chloropropane similarly shows C H subscript 3 C H C H subscript 3, with the numbers 1, 2, and 3 appearing above the carbon atoms from left to right. A C l atom is bonded below carbon 2. The C l atom is red. 2 dash methylpropane similarly shows C H subscript 3 C H C H subscript 3, with the numbers 3, 2, and 1 appearing above the carbon atoms from left to right. A C H subscript 3 group is bonded beneath carbon 2 and is red. 2 comma 4 dash difluorohexane similarly shows C H subscript 3 C H subscript 2 C H C H subscript 2 C H C H subscript 3, with the numbers 6, 5, 4, 3, 2, and 1 appearing above the carbon atoms from left to right. F atoms are bonded to carbons 4 and 2 at the bottom of the structure and are red. 1 dash bromo dash 3 dash chlorohexane similarly shows C H subscript 2 C H subscript 2 C H C H subscript 2 C H subscript 2 C H subscript 3, with numbers 1, 2, 3, 4, 5, and 6 appearing above the carbon atoms from left to right. B r is bonded below carbon 1 and C l is bonded below carbon 3. Both B r and C l are red.

When more than than one substituent is present, either on the same carbon atom or on unlike carbon atoms, the substituents are listed alphabetically. Because the carbon cantlet numbering begins at the finish closest to a substituent, the longest chain of carbon atoms is numbered in such a mode every bit to produce the lowest number for the substituents. The ending -o replaces -ide at the end of the name of an electronegative substituent (in ionic compounds, the negatively charged ion ends with -ide like chloride; in organic compounds, such atoms are treated as substituents and the -o ending is used). The number of substituents of the same type is indicated by the prefixes di- (two), tri- (three), tetra- (four), and so on (for example, difluoro- indicates 2 fluoride substituents).

Example 3

Naming Halogen-substituted Alkanes
Proper name the molecule whose construction is shown here:
This structure shows a C atom bonded to the H atoms and another C atom. This second C atom is bonded to two H atoms and another C atom. This third C atom is bonded to a B r atom and another C atom. This fourth C atom is bonded to two H atoms and a C l atom.

Solution
This structure shows a C atom bonded to the H atoms and another C atom. This second C atom is bonded to two H atoms and another C atom. This third C atom is bonded to an H atom, a B r atom, and another C atom. This fourth C atom is bonded to two H atoms and a C l atom. The C atoms are numbered 4, 3, 2, and 1 from left to right.

The four-carbon concatenation is numbered from the terminate with the chlorine cantlet. This puts the substituents on positions 1 and two (numbering from the other end would put the substituents on positions 3 and 4). Four carbon atoms means that the base of operations proper name of this chemical compound will be butane. The bromine at position 2 will be described past adding 2-bromo-; this volition come at the beginning of the name, since bromo- comes before chloro- alphabetically. The chlorine at position 1 will be described by adding 1-chloro-, resulting in the proper name of the molecule beingness 2-bromo-one-chlorobutane.

Bank check Your Learning
Proper noun the post-obit molecule:
This figure shows a C atom bonded to three H atoms and another C atom. This second C atom is bonded to two H atoms and a third C atom. The third C atom is bonded to two B r atoms and a fourth C atom. This C atom is bonded to an H atom, and I atom, and a fifth C atom. This last C atom is bonded to three H atoms.

Answer:

three,3-dibromo-2-iodopentane

We call a substituent that contains i less hydrogen than the corresponding alkane series an alkyl group. The name of an alkyl group is obtained by dropping the suffix -ane of the alkane series name and adding -yl:
In this figure, methane is named and represented as C with four H atoms bonded above, below, to the left, and to the right of the C. The methyl group is shown, which appears like methane without the right most H. A dash remains at the location where the H was formerly bonded. Ethane is named and represented with two centrally bonded C atoms to which six H atoms are bonded; two above and below each of the two C atoms and to the left and right ends of the linked C atoms. The ethyl group appears as a similar structure with the right-most H atom removed. A dash remains at the location where the H atom was formerly bonded.

The open up bonds in the methyl and ethyl groups betoken that these alkyl groups are bonded to another atom.

Case iv

Naming Substituted Alkanes
Name the molecule whose structure is shown here:
A chain of six carbon atoms, numbered 6, 5, 4, 3, 2, and 1 is shown. Bonded above carbon 3, a chain of two carbons is shown, numbered 1 and 2 moving upward. H atoms are present directly above, below, left and right of all carbon atoms in positions not already taken up in bonding to other carbon atoms.

Solution
The longest carbon chain runs horizontally across the page and contains six carbon atoms (this makes the base of the name hexane, but we will besides need to contain the name of the branch). In this case, we want to number from correct to left (as shown by the blue numbers) and then the co-operative is connected to carbon iii (imagine the numbers from left to right—this would put the branch on carbon 4, violating our rules). The co-operative attached to position 3 of our chain contains two carbon atoms (numbered in scarlet)—so we accept our name for two carbons eth- and attach -yl at the end to signify nosotros are describing a branch. Putting all the pieces together, this molecule is 3-ethylhexane.

Check Your Learning
Name the following molecule:
This figure shows a C atom bonded to three H atoms and another C atom. This C atom is bonded to two H atoms and third C atom. The third C atom is bonded to two H atoms and a fourth C atom. The fourth C atom is bonded to two H atoms and a fifth C atom. This C atom is bonded to an H atom, a sixth C atom in the chain, and another C atom which appears to branch off the chain. The C atom in the branch is bonded to two H atoms and another C atom. This C atom is bonded to two H atoms and another C atom. This third C atom appears to the left of the second and is bonded to three H atoms. The sixth C atom in the chain is bonded to two H atoms and a seventh C atom. The seventh C atom is bonded to two H atoms and an eighth C atom. The eighth C atom is bonded to three H atoms.

Some hydrocarbons tin course more than 1 blazon of alkyl grouping when the hydrogen atoms that would be removed have different "environments" in the molecule. This diversity of possible alkyl groups tin can exist identified in the following manner: The iv hydrogen atoms in a methyl hydride molecule are equivalent; they all take the same surroundings. They are equivalent because each is bonded to a carbon atom (the same carbon cantlet) that is bonded to 3 hydrogen atoms. (It may be easier to see the equivalency in the ball and stick models in Figure 1. Removal of any one of the four hydrogen atoms from methane forms a methyl group. Too, the vi hydrogen atoms in ethane are equivalent (Figure i) and removing whatsoever ane of these hydrogen atoms produces an ethyl group. Each of the six hydrogen atoms is bonded to a carbon atom that is bonded to two other hydrogen atoms and a carbon cantlet. Withal, in both propane and 2–methylpropane, there are hydrogen atoms in two unlike environments, distinguished by the side by side atoms or groups of atoms:
In this figure, propane is shown as a chain of three bonded C atoms. Eight H atoms are shown with three bonded to the first C atom, two to the middle C atom, and three to the third C atom. The H atoms bonded to the middle C atom are purple. 2 dash methylpropane is also shown, which similarly has a chain of three bonded C atoms. In this structure, A C atom is bonded beneath the middle C atom of the chain. Ten H atoms are shown with three bonded to the first C atom, one to the middle C atom, three to the third C atom, and three to the C atom also bonded to the middle C atom. The H atom bonded to the middle C atom is green.

Each of the 6 equivalent hydrogen atoms of the first type in propane and each of the 9 equivalent hydrogen atoms of that type in 2-methylpropane (all shown in black) are bonded to a carbon atom that is bonded to simply one other carbon atom. The two purple hydrogen atoms in propane are of a second blazon. They differ from the six hydrogen atoms of the outset type in that they are bonded to a carbon atom bonded to 2 other carbon atoms. The green hydrogen atom in 2-methylpropane differs from the other ix hydrogen atoms in that molecule and from the purple hydrogen atoms in propane. The light-green hydrogen cantlet in 2-methylpropane is bonded to a carbon atom bonded to three other carbon atoms. Two different alkyl groups can be formed from each of these molecules, depending on which hydrogen atom is removed. The names and structures of these and several other alkyl groups are listed in Figure 4.

This table provides a listing of alkyl groups and corresponding structures. Methyl is shown as C H subscript 3 followed by a dash. Ethyl is shown as C H subscript 3 C H subscript 2 followed by a dash. n dash propyl is shown as C H subscript 3 C H subscript 2 C H subscript 2 followed by a dash. Isopropyl is shown as C H subscript 3 C H C H subscript 3 with a dash extending upward from the middle C. n dash butyl is shown as C H subscript 3 C H subscript 2 C H subscript 2 C H subscript 2 followed by a dash. sec dash butyl is shown as C H subscript 3 C H subscript 2 C H C H subscript 3 with a dash extending upward from the third C counting left to right. Isobutyl is shown as C H subscript 3 C H C H subscript 2 with a dash extending to the right. There is a C H subscript 3 bonded to the middle C. tert dash butyl is shown as C H subscript 3 C C H subscript 3 with a C H subscript 3 group bonded below the middle C and a dash extending upward from the central C.
Effigy 4. This listing gives the names and formulas for various alkyl groups formed by the removal of hydrogen atoms from dissimilar locations.

Note that alkyl groups practise not exist as stable independent entities. They are e'er a role of some larger molecule. The location of an alkyl grouping on a hydrocarbon concatenation is indicated in the aforementioned style as any other substituent:
This figure shows structures of 3 dash ethylheptane, 2 comma 2 comma 4 dash trimethylpentane, and 4 dash isopropylheptane. The 3 dash ethylheptane structure shows C H subscript 3 C H subscript 2 C H subscript 2 C H subscript 2 C H C H subscript 2 C H subscript 3. Under the C atom labeled 3, is a bond to C H subscript 2 C H subscript 3 which appears in red. The C atoms are labeled 7, 6, 5, 4, 3, 2, and 1 from left to right. The 2 comma 2 comma 4 dash trimethylpentane structure shows C H subscript 3 C bonded to C H subscript 2 C H C H subscript 3. The C atoms are labeled 1, 2, 3, 4, and 5 from left to right. The C atom labeled 2 has a C H subscript 3 bonded above it and below it. The C H subscript 3 groups both appear in red. The C atom labeled 4 has a bond above it to C H subscript 3. The C H subscript 3 group appears in red. The 4 dash isopropylheptane structure shows C H subscript 3 C H subscript 2 C H subscript 2 C H C H subscript 2 C H subscript 2 C H subscript 3. From the fourth C counting from left to right, there is a C H group bonded above. Bonded up and to the right and and up to the left of this C H group are C H subscript 3 groups.

Alkanes are relatively stable molecules, but rut or light volition activate reactions that involve the breaking of C–H or C–C unmarried bonds. Combustion is 1 such reaction:

[latex]\text{CH}_4(g)\;+\;two\text{O}_2(thou)\;{\longrightarrow}\;\text{CO}_2(g)\;+\;ii\text{H}_2\text{O}(one thousand)[/latex]

Alkanes burn in the presence of oxygen, a highly exothermic oxidation-reduction reaction that produces carbon dioxide and water. As a issue, alkanes are splendid fuels. For example, methane, CH4, is the principal component of natural gas. Butane, C4H10, used in camping stoves and lighters is an alkane. Gasoline is a liquid mixture of continuous- and branched-chain alkanes, each containing from five to 9 carbon atoms, plus various additives to meliorate its operation equally a fuel. Kerosene, diesel oil, and fuel oil are primarily mixtures of alkanes with higher molecular masses. The master source of these liquid alkane fuels is crude oil, a complex mixture that is separated by fractional distillation. Fractional distillation takes advantage of differences in the boiling points of the components of the mixture (see Effigy five). You may recall that boiling point is a function of intermolecular interactions, which was discussed in the chapter on solutions and colloids.

This figure contains a photo of a refinery, showing large columnar structures. A diagram of a fractional distillation column is also shown. Near the bottom of the column, an arrow pointing into the column from the left shows a point of entry for heated crude oil. The column contains several layers at which different components are removed. At the very bottom, residue materials are removed through a pipe as indicated by an arrow out of the column. At each successive level, different materials are removed through pipes proceeding from the bottom to the top of the column. In order from bottom to top, these materials are fuel oil, followed by diesel oil, kerosene, naptha, gasoline, and refinery gas at the very top. To the right of the column diagram, a double sided arrow is shown that is blue at the top and gradually changes color to red moving downward. The blue top of the arrow is labeled,
Figure 5. In a cavalcade for the partial distillation of rough oil, oil heated to virtually 425 °C in the furnace vaporizes when it enters the base of operations of the tower. The vapors rise through bubble caps in a series of trays in the tower. Equally the vapors gradually absurd, fractions of higher, then of lower, humid points condense to liquids and are drawn off. (credit left: modification of work by Luigi Chiesa)

In a exchange reaction, some other typical reaction of alkanes, ane or more of the alkane's hydrogen atoms is replaced with a different cantlet or group of atoms. No carbon-carbon bonds are broken in these reactions, and the hybridization of the carbon atoms does not change. For example, the reaction between ethane and molecular chlorine depicted here is a commutation reaction:
This diagram illustrates the reaction of ethane and C l subscript 2 to form chloroethane. In this reaction, the structural formula of ethane is shown with two C atoms bonded together and three H atoms bonded to each C atom. The H atom on the far right is red. Ethane is added to C l bonded to C l, followed by an arrow that points right. The arrow is labeled,

The C–Cl portion of the chloroethane molecule is an case of a functional group, the role or moiety of a molecule that imparts a specific chemical reactivity. The types of functional groups present in an organic molecule are major determinants of its chemical backdrop and are used equally a means of classifying organic compounds as detailed in the remaining sections of this chapter.

Alkenes

Organic compounds that contain one or more than double or triple bonds betwixt carbon atoms are described every bit unsaturated. Yous take likely heard of unsaturated fats. These are complex organic molecules with long chains of carbon atoms, which incorporate at least one double bond betwixt carbon atoms. Unsaturated hydrocarbon molecules that contain one or more double bonds are chosen alkenes. Carbon atoms linked by a double bond are jump together by two bonds, 1 σ bail and one π bond. Double and triple bonds give rise to a unlike geometry around the carbon atom that participates in them, leading to important differences in molecular shape and properties. The differing geometries are responsible for the different properties of unsaturated versus saturated fats.

Ethene, C2H4, is the simplest alkene. Each carbon cantlet in ethene, commonly called ethylene, has a trigonal planar construction. The 2nd member of the serial is propene (propylene) (Figure 6); the butene isomers follow in the series. Four carbon atoms in the chain of butene allows for the formation of isomers based on the position of the double bond, too as a new form of isomerism.

Lewis structural formulas show carbon and hydrogen element symbols and bonds between the atoms. The first structure in this row shows two bonded C atoms with a double bond between them. Each C atom has two H atoms bonded to it as well. The second structure in the row shows three bonded C atoms with a double bond up and to the right between the first and second C atoms moving left to right across the chain, and a single bond down and to the right between the second and third C atom. The first C atom has two H atoms bonded to it, the second C atom has one H atom bonded to it, and the third C atom has three H atoms bonded to it. The third structure shows four bonded C atoms with one bonded up and to the right to a C atom, down and to the right to a C atom, and double bonded up and to the right to a C atom. The first C atom, moving from left to right, has three H atoms bonded to it. The second C atom has two H atoms bonded to it. The third C atom has one H atom bonded to it, and the fourth C atom has two H atoms bonded to it. In the second row, ball-and-stick models for the structures are shown. In these representations, single bonds are represented with sticks, double bonds are represented with two parallel sticks, and elements are represented with balls. Carbon atoms are black and hydrogen atoms are white in this image. In the third row, space-filling models are shown. In these models, atoms are enlarged and pushed together, without sticks to represent bonds. In the final row, names are provided. The molecule with the double bond between two C atoms is named ethene. The molecule with the double bond between the first and second C atoms in the chain of three is named propene. The molecule with the double bond between the carbon atoms in the chain of four is named 1 dash butene.
Figure 6. Expanded structures, ball-and-stick structures, and infinite-filling models for the alkenes ethene, propene, and 1-butene are shown.

Ethylene (the mutual industrial name for ethene) is a basic raw material in the production of polyethylene and other important compounds. Over 135 million tons of ethylene were produced worldwide in 2010 for use in the polymer, petrochemical, and plastic industries. Ethylene is produced industrially in a procedure called bully, in which the long hydrocarbon bondage in a petroleum mixture are cleaved into smaller molecules.

Recycling Plastics

Polymers (from Greek words poly meaning "many" and mer meaning "parts") are big molecules made upward of repeating units, referred to as monomers. Polymers can be natural (starch is a polymer of saccharide residues and proteins are polymers of amino acids) or constructed [like polyethylene, polyvinyl chloride (PVC), and polystyrene]. The variety of structures of polymers translates into a broad range of properties and uses that make them integral parts of our everyday lives. Calculation functional groups to the construction of a polymer can result in significantly different properties (run into the word about Kevlar later in this chapter).

An example of a polymerization reaction is shown in Effigy 7. The monomer ethylene (C2Hiv) is a gas at room temperature, but when polymerized, using a transition metallic catalyst, it is transformed into a solid material made up of long chains of –CHtwo– units called polyethylene. Polyethylene is a commodity plastic used primarily for packaging (bags and films).

This diagram has three rows, showing ethylene reacting to form polyethylene. In the first row, Lewis structural formulas show three molecules of ethylene being added together, which are each composed of two doubly bonded C atoms, each with two bonded H atoms. Ellipses, or three dots, are present before and after the molecule structures, which in turn are followed by an arrow pointing right. On the right side of the arrow, the ellipses or dots again appear to the left of a dash that connects to a chain of 7 C atoms, each with H atoms connected above and below. A dash appears at the end of the chain, which in turn is followed by ellipses or dots. The reaction diagram is repeated in the second row using ball-and-stick models for the structures. In these representations, single bonds are represented with sticks, double bonds are represented with two parallel sticks, and elements are represented with balls. Carbon atoms are black and hydrogen atoms are white in this image. In the third row, space-filling models are shown. In these models, atoms are enlarged spheres which are pushed together, without sticks to represent bonds.
Figure 7. The reaction for the polymerization of ethylene to polyethylene is shown.

Polyethylene is a member of i subset of synthetic polymers classified as plastics. Plastics are synthetic organic solids that tin be molded; they are typically organic polymers with loftier molecular masses. Most of the monomers that go into common plastics (ethylene, propylene, vinyl chloride, styrene, and ethylene terephthalate) are derived from petrochemicals and are not very biodegradable, making them candidate materials for recycling. Recycling plastics helps minimize the need for using more than of the petrochemical supplies and also minimizes the environmental damage acquired by throwing away these nonbiodegradable materials.

Plastic recycling is the process of recovering waste material, scrap, or used plastics, and reprocessing the textile into useful products. For example, polyethylene terephthalate (soft potable bottles) can be melted downward and used for plastic furniture, in carpets, or for other applications. Other plastics, similar polyethylene (bags) and polypropylene (cups, plastic food containers), tin be recycled or reprocessed to be used once again. Many areas of the country have recycling programs that focus on 1 or more of the commodity plastics that accept been assigned a recycling code (come across Figure eight). These operations have been in outcome since the 1970s and accept made the production of some plastics amidst the most efficient industrial operations today.

This table shows recycling symbols, names, and uses of various types of plastics. Symbols are shown with three arrows in a triangular shape surrounding a number. Number 1 is labeled P E T E. The related plastic, polyethylene terephthalate (P E T E), is used in soda bottles and oven-ready food trays. Number 2 is labeled H D P E. The related plastic is high-density polyethylene (H D P E), which is used in bottles for milk and dishwashing liquids. Number 3 is labeled V. The related plastic is polyvinyl chloride or (P V C). This plastic is used in food trays, plastic wrap, and bottles for mineral water and shampoo. Number 4 is labeled L D P E. This plastic is low density polyethylene (L D P E). It is used in shopping bags and garbage bags. Number 5 is labeled P P. The related plastic is polypropylene (P P). It is used in margarine tubs and microwaveable food trays. Number 6 is labeled P S. The related plastic is polystyrene (P S). It is used in yogurt tubs, foam meat trays, egg cartons, vending cups, plastic cutlery, and packaging for electronics and toys. Number 7 is labeled other for any other plastics. Items in this category include those plastic materials that do not fit any other category. Melamine used in plastic plates and cups is an example.
Figure 8. Each type of recyclable plastic is imprinted with a code for easy identification.

The proper name of an alkene is derived from the name of the alkane with the same number of carbon atoms. The presence of the double bond is signified by replacing the suffix -ane with the suffix -ene. The location of the double bond is identified by naming the smaller of the numbers of the carbon atoms participating in the double bail:
Four structural formulas and names are shown. The first shows two red C atoms connected by a red double bond illustrated with two parallel line segments. H atoms are bonded above and below to the left of the left-most C atom. Two more H atoms are similarly bonded to the right of the C atom on the right. Beneath this structure the name ethene and alternate name ethylene are shown. The second shows three C atoms bonded together with a red double bond between the red first and second C atoms moving left to right across the three-carbon chain. H atoms are bonded above and below to the left of the C atom to the left. A single H is bonded above the middle C atom. Three more H atoms are bonded above, below, and to the right of the third C atom. Beneath this structure the name propene and alternate name propylene is shown. The third shows four C atoms bonded together, numbered one through four moving left to right with a red double bond between the red first and second carbon in the chain. H atoms are bonded above and below to the left of the C atom to the left. A single H is bonded above the second C atom. H atoms are bonded above and below the third C atom. Three more H atoms are bonded above, below, and to the right of the fourth C atom. Beneath this structure the name 1 dash butene is shown. The fourth shows four C atoms bonded together, numbered one through four moving left to right with a red double bond between the red second and third C atoms in the chain. H atoms are bonded above, below, and to the left of the left-most C atom. A single H atom is bonded above the second C atom. A single H atom is bonded above the third C atom. Three more H atoms are bonded above, below, and to the right of the fourth C atom. Beneath this structure the name 2 dash butene is shown.

Isomers of Alkenes

Molecules of 1-butene and 2-butene are structural isomers; the arrangement of the atoms in these 2 molecules differs. As an case of organisation differences, the first carbon atom in 1-butene is bonded to 2 hydrogen atoms; the commencement carbon cantlet in two-butene is bonded to three hydrogen atoms.

The compound 2-butene and another alkenes also form a 2nd type of isomer called a geometric isomer. In a set of geometric isomers, the same types of atoms are fastened to each other in the same social club, but the geometries of the 2 molecules differ. Geometric isomers of alkenes differ in the orientation of the groups on either side of a [latex]\text{C}\;=\;\text{C}[/latex] bond.

Carbon atoms are gratuitous to rotate effectually a single bond but not around a double bail; a double bond is rigid. This makes it possible to take ii isomers of 2-butene, ane with both methyl groups on the same side of the double bond and one with the methyl groups on opposite sides. When structures of butene are drawn with 120° bond angles effectually the sp two-hybridized carbon atoms participating in the double bond, the isomers are apparent. The 2-butene isomer in which the two methyl groups are on the aforementioned side is chosen a cis-isomer; the one in which the ii methyl groups are on contrary sides is called a trans-isomer (Figure 9). The unlike geometries produce different physical properties, such as boiling point, that may make separation of the isomers possible:

The figure illustrates three ways to represent isomers of butene. In the first row of the figure, Lewis structural formulas show carbon and hydrogen element symbols and bonds between the atoms. The first structure in this row shows a C atom with a double bond to another C atom which is bonded down and to the right to C H subscript 2 which, in turn, is bonded to C H subscript 3. The first C atom, moving from left to right, has two H atoms bonded to it and the second C atom has one H atom bonded to it. The second structure in the row shows a C atom with a double bond to another C atom. The first C atom is bonded to an H atom up and to the left and C H subscript 3 down and to the left. The second C atom is bonded to an H atom up and to the right and C H subscript 3 down and to the right. Both C H subscript 3 structures appear in red. The third structure shows a C atom with a double bond to another C atom. The first C atom from the left is bonded up to a the left to C H subscript 3 which appears and red. It is also bonded down and to the left to an H atom. The second C atom is bonded up and to the right to an H atom and down and to the left to C H subscript 3 which appears in red. In the second row, ball-and-stick models for the structures are shown. In these representations, single bonds are represented with sticks, double bonds are represented with two parallel sticks, and elements are represented with balls. C atoms are black and H atoms are white in this image. In the third row, space-filling models are shown. In these models, atoms are enlarged and pushed together, without sticks to represent bonds. In the final row, names are provided. The molecule with the double bond between the first and second carbons is named 1 dash butene. The two molecules with the double bond between the second and third carbon atoms is called 2 dash butene. The first model, which has both C H subscript 3 groups beneath the double bond is called the cis isomer. The second which has the C H subscript 3 groups on opposite sides of the double bond is named the trans isomer.
Figure 9. These molecular models show the structural and geometric isomers of butene.

Alkenes are much more reactive than alkanes because the [latex]\text{C}\;=\;\text{C}[/latex] moiety is a reactive functional group. A π bond, being a weaker bail, is disrupted much more hands than a σ bond. Thus, alkenes undergo a feature reaction in which the π bond is broken and replaced by ii σ bonds. This reaction is called an addition reaction. The hybridization of the carbon atoms in the double bond in an alkene changes from sp 2 to sp 3 during an improver reaction. For example, halogens add together to the double bail in an alkene instead of replacing hydrogen, every bit occurs in an alkane:
This diagram illustrates the reaction of ethene and C l subscript 2 to form 1 comma 2 dash dichloroethane. In this reaction, the structural formula of ethane is shown. It has a double bond between the two C atoms with two H atoms bonded to each C atom plus C l bonded to C l. This is shown on to the left of an arrow. The two C atoms and the double bond between them are shown in red. To the right of the arrow, the 1 comma 2 dash dichloroethane molecule is shown. It has only single bonds and each C atom has a C l with three pairs of electron dots bonded beneath it. The C and C l atoms, single bond between them, and electron pairs are shown in red. Each C atom also has two H atoms bonded to it.

Example v

Alkene Reactivity and Naming
Provide the IUPAC names for the reactant and production of the halogenation reaction shown here:
The left side of a reaction and arrow are shown with an empty product side. On the left, C H subscript 3 is bonded down and to the right to C H which has a double bond to another C H. The second C H is bonded up and to the right to C H subscript 2 which is also bonded to C H subscript 3. A plus sign is shown with a C l atom bonded to a C l atom following it. This is also followed by a reaction arrow.

Solution
The reactant is a v-carbon concatenation that contains a carbon-carbon double bond, so the base of operations name will be pentene. We begin counting at the terminate of the chain closest to the double bond—in this case, from the left—the double bond spans carbons 2 and 3, so the name becomes ii-pentene. Since there are two carbon-containing groups attached to the two carbon atoms in the double bond—and they are on the same side of the double bond—this molecule is the cis-isomer, making the name of the starting alkene cis-2-pentene. The product of the halogenation reaction will have ii chlorine atoms attached to the carbon atoms that were a part of the carbon-carbon double bond:
C H subscript 3 is bonded down and to the right to C H which is bonded down and to the left to C l. C H is also bonded to another C H which is bonded down and to the right to C l and up and to the right to C H subscript 2. C H subscript 2 is also bonded to C H subscript 3.

This molecule is now a substituted methane series and will be named as such. The base of the name will exist pentane. We will count from the end that numbers the carbon atoms where the chlorine atoms are attached as two and 3, making the proper noun of the product ii,3-dichloropentane.

Check Your Learning
Provide names for the reactant and product of the reaction shown:
This shows a C atom bonded to three H atoms and another C atom. This second C atom is bonded to two H atoms and a third C atom. This third C atom is bonded to one H atom and also forms a double bond with a fourth C atom. This fourth C atom is bonded to one H atom and a fifth C atom. This fifth C atom is bonded to two H atoms and a sixth C atom. This sixth C atom is bonded to three H atoms. There is a plus sign followed by a C l atom bonded to another C l atom. There is a reaction arrow. no products are shown.

Answer:

reactant: cis-3-hexene product: 3,4-dichlorohexane

Alkynes

Hydrocarbon molecules with one or more triple bonds are called alkynes; they make up another series of unsaturated hydrocarbons. Ii carbon atoms joined past a triple bail are bound together past one σ bond and two π bonds. The sp-hybridized carbons involved in the triple bond have bond angles of 180°, giving these types of bonds a linear, rod-like shape.

The simplest member of the alkyne series is ethyne, CtwoH2, usually called acetylene. The Lewis structure for ethyne, a linear molecule, is:
The structural formula and name for ethyne, also known as acetylene, are shown. In red, two C atoms are shown with a triple bond illustrated by three horizontal line segments between them. Shown in black at each end of the structure, a single H atom is bonded.

The IUPAC classification for alkynes is like to that for alkenes except that the suffix -yne is used to indicate a triple bond in the concatenation. For example, [latex]\text{CH}_3\text{CH}_2\text{C}\;{\equiv}\;\text{CH}[/latex] is chosen 1-butyne.

Instance 6

Structure of Alkynes
Describe the geometry and hybridization of the carbon atoms in the following molecule:
A structural formula is shown with C H subscript 3 bonded to a C atom which is triple bonded to another C atom which is bonded to C H subscript 3. Each C atom is labeled 1, 2, 3, and 4 from left to right.

Solution
Carbon atoms 1 and 4 have four single bonds and are thus tetrahedral with sp iii hybridization. Carbon atoms ii and 3 are involved in the triple bail, so they have linear geometries and would exist classified equally sp hybrids.

Check Your Learning
Identify the hybridization and bond angles at the carbon atoms in the molecule shown:
A structural formula is shown with an H atom bonded to a C atom. The C atom has a triple bond with another C atom which is also bonded to C H. The C H has a double bond with another C H which is also bonded up and to the right to C H subscript 3. Each C atom is labeled 1, 2, 3, 4, or 5 from left to right.

Answer:

carbon one: sp, 180°; carbon 2: sp, 180°; carbon 3: sp 2, 120°; carbon 4: sp 2, 120°; carbon 5: sp 3, 109.5°

Chemically, the alkynes are similar to the alkenes. Since the [latex]\text{C}\;{\equiv}\;\text{C}[/latex] functional group has two π bonds, alkynes typically react fifty-fifty more readily, and react with twice as much reagent in addition reactions. The reaction of acetylene with bromine is a typical example:
This diagram illustrates the reaction of ethyne and two molecules of B r subscript 2 to form 1 comma 1 comma 2 comma 2 dash tetrabromoethane. In this reaction, the structural formula of ethyne, an H atom bonded to a red C atom with a red triple bond to another red C atom bonded to a black H atom, plus B r bonded to B r plus B r bonded to B r is shown to the left of an arrow. On the right, the form 1 comma 1 comma 2 comma 2 dash tetrabromoethane molecule is shown. It has an H atom bonded to a C atom which is bonded to another C atom which is bonded to an H atom. Each C atom is bonded above and below to a B r atom. Each B r atom has three pairs of electron dots. The C and B r atoms, single bond between them, and electron pairs are shown in red.

Acetylene and the other alkynes besides burn readily. An acetylene torch takes reward of the high estrus of combustion for acetylene.

Aromatic Hydrocarbons

Benzene, C6H6, is the simplest member of a big family of hydrocarbons, chosen aromatic hydrocarbons. These compounds contain ring structures and exhibit bonding that must be described using the resonance hybrid concept of valence bond theory or the delocalization concept of molecular orbital theory. (To review these concepts, refer to the earlier capacity on chemical bonding). The resonance structures for benzene, CsixHsix, are:
This structural formula shows a six carbon hydrocarbon ring. On the left side there are six C atoms. The C atom on top and to the left forms a single bond to the C atom on the top and to the right. The C atom has a double bond to another C atom which has a single bond to a C atom. That C atom has a double bond to another C atom which has a single bond to a C atom. That C atom forms a double bond with another C atom. Each C atom has a single bond to an H atom. There is a double sided arrow and the structure on the right is almost identical to the structure on the left. The structure on the right shows double bonds where the structure on the left showed single bonds. The structure on the right shows single bonds where the stucture on the left showed double bonds.

Valence bond theory describes the benzene molecule and other planar aromatic hydrocarbon molecules as hexagonal rings of sp 2-hybridized carbon atoms with the unhybridized p orbital of each carbon atom perpendicular to the plane of the band. Three valence electrons in the sp 2 hybrid orbitals of each carbon cantlet and the valence electron of each hydrogen cantlet form the framework of σ bonds in the benzene molecule. The fourth valence electron of each carbon atom is shared with an side by side carbon atom in their unhybridized p orbitals to yield the π bonds. Benzene does non, however, showroom the characteristics typical of an alkene. Each of the half-dozen bonds between its carbon atoms is equivalent and exhibits properties that are intermediate between those of a C–C unmarried bond and a [latex]\text{C}\;=\;\text{C}[/latex] double bail. To represent this unique bonding, structural formulas for benzene and its derivatives are typically drawn with single bonds betwixt the carbon atoms and a circle within the ring as shown in Figure 10.

A six carbon hydrocarbon ring structural formula is shown. Each C atom is bonded to only one H atom. A circle is at the center of the ring.
Figure 10. This condensed formula shows the unique bonding structure of benzene.

There are many derivatives of benzene. The hydrogen atoms can be replaced by many different substituents. Effluvious compounds more readily undergo substitution reactions than addition reactions; replacement of one of the hydrogen atoms with another substituent will exit the delocalized double bonds intact. The following are typical examples of substituted benzene derivatives:
Three structural formulas are shown. The first is labeled toluene. This molecule has a six carbon hydrocarbon ring in which five of the C atoms are each bonded to only one H atom. At the upper right of the ring, the C atom that does not have a bonded H atom has a red C H subscript 3 group attached. A circle is at the center of the ring. The second is labeled xylene. This molecule has a six carbon hydrocarbon ring in which four of the C atoms are each bonded to only one H atom. At the upper right and right of the ring, the two C atoms that do not have bonded H atoms have C H subscript 3 groups attached. These C H subscript 3 groups appear in red. A circle is at the center of the ring. The third is labeled styrene. This molecule has a six carbon hydrocarbon ring in which five of the carbon atoms are each bonded to only one H atom. At the upper right of the ring, the carbon that does not have a bonded H atom has a red C H double bond C H subscript 2 group attached. A circle is at the center of the ring.

Toluene and xylene are important solvents and raw materials in the chemic industry. Styrene is used to produce the polymer polystyrene.

Example seven

Structure of Aromatic Hydrocarbons
I possible isomer created by a substitution reaction that replaces a hydrogen atom fastened to the effluvious ring of toluene with a chlorine cantlet is shown hither. Draw ii other possible isomers in which the chlorine atom replaces a different hydrogen atom fastened to the effluvious ring:
Two structural formulas are shown. The first has a six carbon hydrocarbon ring in which four of the carbon atoms are each bonded to only one H atom. At the upper right of the ring, the carbon that does not have a bonded H atom has a C H subscript 3 group attached. The C to the lower right has a C l atom attached. A circle is at the center of the ring. The second molecule has a hexagon with a circle inside. From a vertex of the hexagon at the upper right a C H subscript 3 group is attached. From the vertex at the lower right, a C l atom is attached.

Solution
Since the half-dozen-carbon ring with alternating double bonds is necessary for the molecule to be classified as aromatic, advisable isomers can be produced merely by changing the positions of the chloro-substituent relative to the methyl-substituent:
Two pairs of structural formulas are shown. The first has a six carbon hydrocarbon ring in which four of the C atoms are each bonded to only one H atom. At the upper right of the ring, the C atom that does not have a bonded H atom has a C H subscript 3 group attached. The C atom to the right has a C l atom attached. A circle is at the center of the ring. The second molecule in the first pair has a hexagon with a circle inside. From a vertex of the hexagon at the upper right a C H subscript 3 group is attached. From the vertex at the right, a C l atom is attached. The second pair first shows a six carbon hydrocarbon ring in which four of the C atoms are each bonded to only one H atom. A C l atom is attached to the left-most C atom and a C H subscript 3 group is attached to the right-most C atom. A circle is at the center of the ring. The second molecule in the pair has a hexagon with a circle inside. A C H subscript 3 group is attached to a vertex on the right side of the hexagon and to a vertex on the left side, a C l atom is bonded.

Check Your Learning
Draw three isomers of a vi-membered effluvious ring compound substituted with 2 bromines.

Answer:
Three pairs of structural formulas are shown. The first has a six carbon hydrocarbon ring in which four of the C atoms are each bonded to only one H atom. At the upper right and right of the ring, the two C atoms that do not have bonded H atoms have one B r atom bonded each. A circle is at the center of the ring. Beneath this structure, a similar structure is shown which has a hexagon with a circle inside. From vertices of the hexagon at the upper right and right single B r atoms are attached. The second has a six carbon hydrocarbon ring in which four of the C atoms are each bonded to only one H atom. At the upper right and lower right of the ring, the two C atoms that do not have bonded H atoms have a single B r atom bonded each. A circle is at the center of the ring. Beneath this structure, a similar structure is shown which has a hexagon with a circle inside. From vertices of the hexagon at the upper right and lower right single B r atoms are attached. The third has a six carbon hydrocarbon ring in which four of the C atoms are each bonded to only one H atom. At the upper right and lower left of the ring, the two C atoms that do not have bonded H atoms have B r atoms bonded. A circle is at the center of the ring. Beneath this structure, a similar structure is shown which has a hexagon with a circle inside. From vertices of the hexagon at the upper right and lower left, single B r atoms are attached.

Primal Concepts and Summary

Strong, stable bonds between carbon atoms produce complex molecules containing chains, branches, and rings. The chemical science of these compounds is called organic chemistry. Hydrocarbons are organic compounds composed of merely carbon and hydrogen. The alkanes are saturated hydrocarbons—that is, hydrocarbons that contain only single bonds. Alkenes comprise one or more than carbon-carbon double bonds. Alkynes contain one or more than carbon-carbon triple bonds. Effluvious hydrocarbons contain ring structures with delocalized π electron systems.

Chemistry Cease of Chapter Exercises

  1. Write the chemical formula and Lewis structure of the following, each of which contains five carbon atoms:

    (a) an paraffin

    (b) an alkene

    (c) an alkyne

  2. What is the deviation between the hybridization of carbon atoms' valence orbitals in saturated and unsaturated hydrocarbons?
  3. On a microscopic level, how does the reaction of bromine with a saturated hydrocarbon differ from its reaction with an unsaturated hydrocarbon? How are they like?
  4. On a microscopic level, how does the reaction of bromine with an alkene differ from its reaction with an alkyne? How are they like?
  5. Explain why unbranched alkenes can form geometric isomers while unbranched alkanes cannot. Does this caption involve the macroscopic domain or the microscopic domain?
  6. Explicate why these two molecules are non isomers:
    Two structural formulas are shown. In the first, a chain of six carbon atoms with a single double bond between carbons two and three counting right to left across the molecule is shown with twelve total H atoms bonded. H atoms are bonded at each end of the molecule as well as above. H atoms are also bonded below all C atoms except those involved in the double bond. In the second structure, a hydrocarbon chain of five C atoms connected by single bonds is shown. A single C with three attached H atoms is bonded beneath the second carbon counting right to left across the molecule.
  7. Explain why these 2 molecules are non isomers:
    Two structural formulas are shown. In the first, a horizontal hydrocarbon chain consisting of six singly bonded C atoms is shown. Each C atom has an H atom bonded above and below it. The two C atoms on either end of the chain each have a third H atom bonded to them. In the second structure, a horizontal hydrocarbon chain composed of five C atoms connected by single bonds is shown with a sixth C atom singly bonded beneath the right-most C atom. The first C atom (from left to right) has three H atoms bonded to it. The second C atom has two H atoms bonded to it. The third C atom has two H atoms bonded to it. The fourth C atom has two H atoms bonded to it. The fifth C atom has two H atoms bonded to it. The C atom bonded below the fifth C atom has three H atoms bonded to it.
  8. How does the carbon-cantlet hybridization modify when polyethylene is prepared from ethylene?
  9. Write the Lewis construction and molecular formula for each of the following hydrocarbons:

    (a) hexane

    (b) 3-methylpentane

    (c) cis-3-hexene

    (d) iv-methyl-1-pentene

    (e) iii-hexyne

    (f) four-methyl-2-pentyne

  10. Write the chemical formula, condensed formula, and Lewis construction for each of the following hydrocarbons:

    (a) heptane

    (b) 3-methylhexane

    (c) trans-three-heptene

    (d) 4-methyl-1-hexene

    (e) 2-heptyne

    (f) 3,4-dimethyl-1-pentyne

  11. Give the consummate IUPAC name for each of the following compounds:

    (a) [latex]\text{CH}_3\text{CH}_2\text{CBr}_2\text{CH}_3[/latex]

    (b) [latex](\text{CH}_3)_3\text{CCl}[/latex]

    (c)
    This structure shows a hydrocarbon chain composed of C H subscript 3 C H C H subscript 2 C H subscript 3 with a C H subscript 3 group attached beneath the second C atom counting left to right.

    (d) [latex]\text{CH}_3\text{CH}_2\text{C}\;{\equiv}\;\text{CH\;CH}_3\text{CH}_2\text{C}\;{\equiv}\;\text{CH}[/latex]

    (e)
    This structure shows a horizontal chain composed of C H subscript 3 C F C H subscript 2 C H subscript 2 C H subscript 2 C H subscript 3 with a C H subscript 2 C H triple bond C H group attached beneath the second C atom counting left to right.

    (f)
    This structure shows two double bounded C atoms with C l attached to the upper left, C H subscript 3 attached to the lower right, and H atoms attached to the upper right and lower left in the structure.

    (grand) [latex](\text{CH}_3)_2\text{CHCH}_2\text{CH} = \text{CH}_2[/latex]

  12. Give the consummate IUPAC name for each of the following compounds:

    (a) [latex](\text{CH}_3)_2\text{CHF}[/latex]

    (b) [latex]\text{CH}_3\text{CHClCHClCH}_3[/latex]

    (c)
    This structure shows a hydrocarbon chain composed of C H subscript 3 C H C H subscript 3 with a C H subscript 2 C H subscript 3 group attached beneath the second C atom counting left to right.

    (d) [latex]\text{CH}_3\text{CH}_2\text{CH} = \text{CHCH}_3[/latex]

    (e)
    This structure shows a hydrocarbon chain composed of C H subscript 3 C H subscript 2 C H subscript 2 C H B r C H subscript 2 C H subscript 3 with a C H subscript 2 C H double bond C H subscript 2 group attached beneath the second C atom counting left to right.

    (f) [latex](\text{CH}_3)_3\text{CCH}_2\text{C}{\equiv}\text{CH}[/latex]

  13. Butane is used as a fuel in dispensable lighters. Write the Lewis structure for each isomer of butane.
  14. Write Lewis structures and proper noun the five structural isomers of hexane.
  15. Write Lewis structures for the cis–trans isomers of [latex]\text{CH}_3\text{CH} = \text{CHCl}[/latex].
  16. Write structures for the three isomers of the aromatic hydrocarbon xylene, [latex]\text{C}_6\text{H}_4(\text{CH}_3)_2[/latex].
  17. Isooctane is the common proper noun of the isomer of [latex]\text{C}_8\text{H}_18[/latex] used equally the standard of 100 for the gasoline octane rating:
    The hydrocarbon molecular structure shown includes C H subscript 3 C H C H subscript 2 C C H subscript 3. There is a C H subscript 3 group bonded to the second C atom in the chain (from left to right). There are two C H subscript 3 groups bonded above and below the fourth C atom in the chain.

    (a) What is the IUPAC name for the compound?

    (b) Name the other isomers that contain a five-carbon chain with iii methyl substituents.

  18. Write Lewis structures and IUPAC names for the alkyne isomers of [latex]\text{C}_4\text{H}_6[/latex].
  19. Write Lewis structures and IUPAC names for all isomers of [latex]\text{C}_4\text{H}_9\text{Cl}[/latex].
  20. Name and write the structures of all isomers of the propyl and butyl alkyl groups.
  21. Write the structures for all the isomers of the [latex]-\text{C}_5\text{H}_{xi}[/latex] alkyl group.
  22. Write Lewis structures and describe the molecular geometry at each carbon cantlet in the post-obit compounds:

    (a) cis-3-hexene

    (b) cis-1-chloro-2-bromoethene

    (c) two-pentyne

    (d) transhalf dozen-ethyl-vii-methyl-ii-octene

  23. Benzene is one of the compounds used as an octane enhancer in unleaded gasoline. It is manufactured by the catalytic conversion of acetylene to benzene:[latex]3\text{C}_2\text{H}_2\;{\longrightarrow}\;\text{C}_6\text{H}_6[/latex]

    Depict Lewis structures for these compounds, with resonance structures as advisable, and determine the hybridization of the carbon atoms in each.

  24. Teflon is prepared by the polymerization of tetrafluoroethylene. Write the equation that describes the polymerization using Lewis symbols.
  25. Write 2 complete, balanced equations for each of the post-obit reactions, one using condensed formulas and one using Lewis structures.

    (a) i mol of i-butyne reacts with ii mol of iodine.

    (b) Pentane is burned in air.

  26. Write two complete, counterbalanced equations for each of the following reactions, one using condensed formulas and i using Lewis structures.

    (a) 2-butene reacts with chlorine.

    (b) benzene burns in air.

  27. What mass of 2-bromopropane could be prepared from 25.5 g of propene? Assume a 100% yield of product.
  28. Acetylene is a very weak acrid; however, it will react with moist silverish(I) oxide and form h2o and a chemical compound composed of argent and carbon. Addition of a solution of HCl to a 0.2352-m sample of the compound of silver and carbon produced acetylene and 0.2822 g of AgCl.

    (a) What is the empirical formula of the chemical compound of silver and carbon?

    (b) The production of acetylene on addition of HCl to the compound of silverish and carbon suggests that the carbon is present as the acetylide ion, [latex]\text{C}_2^{\;\;2-}[/latex]. Write the formula of the compound showing the acetylide ion.

  29. Ethylene can be produced by the pyrolysis of ethane:[latex]\text{C}_2\text{H}_6\;{\longrightarrow}\;\text{C}_2\text{H}_4\;+\;\text{H}_2[/latex]

    How many kilograms of ethylene is produced by the pyrolysis of one.000 × ten3 kg of ethane, bold a 100.0% yield?

Glossary

addition reaction
reaction in which a double carbon-carbon bail forms a single carbon-carbon bond past the addition of a reactant. Typical reaction for an alkene.
alkane series
molecule consisting of only carbon and hydrogen atoms connected by single (σ) bonds
alkene
molecule consisting of carbon and hydrogen containing at least ane carbon-carbon double bond
alkyl grouping
substituent, consisting of an paraffin missing one hydrogen atom, attached to a larger structure
alkyne
molecule consisting of carbon and hydrogen containing at to the lowest degree one carbon-carbon triple bond
aromatic hydrocarbon
cyclic molecule consisting of carbon and hydrogen with delocalized alternating carbon-carbon single and double bonds, resulting in enhanced stability
functional group
part of an organic molecule that imparts a specific chemical reactivity to the molecule
organic compound
natural or constructed compound that contains carbon
saturated hydrocarbon
molecule containing carbon and hydrogen that has only single bonds between carbon atoms
skeletal structure
autograph method of drawing organic molecules in which carbon atoms are represented by the ends of lines and bends in between lines, and hydrogen atoms attached to the carbon atoms are not shown (but are understood to be present by the context of the structure)
substituent
branch or functional grouping that replaces hydrogen atoms in a larger hydrocarbon concatenation
substitution reaction
reaction in which one atom replaces some other in a molecule

Solutions

Answers to Chemistry End of Chapter Exercises

1. In that location are several sets of answers; one is:

(a) [latex]\text{C}_5\text{H}_{12}[/latex]
A chain of five C atoms with single bonds is shown. Each C atom has an H atom bonded above and below it. The C atoms on the end of the chain have a third H atom bonded to them each.
;

(b) [latex]\text{C}_5\text{H}_{10}[/latex]
A chain of five C atoms is shown. The first C atom (from left to right) forms a single bond with the second C atom. The second C atom forms a single bond with the third C atom. The third C atom forms a double bond with the fourth C atom. The fourth C atom forms a single bond to the fifth C atom. The first C atom (from left to right) as three H atoms bonded to it. The second C atom has two H atoms bonded to it. The third C atom has one H atom bonded to it. The fourth C atom has one H atom bonded to it. The fifth C atom as three H atoms bonded to it.
;

(c) [latex]\text{C}_5\text{H}_8[/latex]
A chain of five carbon atoms is shown. The first C atom (from left to right) forms a single bond with the second C atom. The second C atom forms a single bond with the third C atom. The third C atom forms a triple bond with the fourth C atom. The fourth C atom forms a single bond to the fifth C atom. The first C atom has three H atoms bonded to it. The second C atom has two H atoms bonded to it. The fifth C atom has three H atoms bonded to it.

3. Both reactions result in bromine being incorporated into the structure of the production. The difference is the fashion in which that incorporation takes place. In the saturated hydrocarbon, an existing C–H bond is cleaved, and a bail between the C and the Br can then be formed. In the unsaturated hydrocarbon, the simply bond broken in the hydrocarbon is the π bond whose electrons can be used to course a bond to ane of the bromine atoms in Brii (the electrons from the Br–Br bond course the other C–Br bond on the other carbon that was office of the π bond in the starting unsaturated hydrocarbon).

5. Unbranched alkanes take free rotation almost the C–C bonds, yielding all orientations of the substituents well-nigh these bonds equivalent, interchangeable by rotation. In the unbranched alkenes, the inability to rotate about the [latex]\text{C}\;=\;\text{C}[/latex] bond results in fixed (unchanging) substituent orientations, thus permitting different isomers. Since these concepts pertain to phenomena at the molecular level, this explanation involves the microscopic domain.

7. They are the same chemical compound because each is a saturated hydrocarbon containing an unbranched chain of half dozen carbon atoms.

nine. (a) [latex]\text{C}_6\text{H}_{14}[/latex]
This figure shows a horizontal hydrocarbon chain consisting of six singly bonded carbon atoms. Each C atom has an H atom bonded above and below it. The two C atoms on either end of the chain each of a third H atom bonded to it.
;

(b) [latex]\text{C}_6\text{H}_{14}[/latex]
This figure shows five C atoms bonded together with a sixth C atom bonded below the chain. The first C atom (from left to right) has three H atoms bonded to it and is also bonded to another C atom. The second C atom has two H atoms bonded above and below it and is also bonded to another C atom. The third C atom has an H atom bonded above it and a C atom bonded below it. The C atom bonded below the third C atom in the chain has three H atoms bonded to it. The third C atom is also bonded to another C atom. The fourth C atom in the chain has two H atoms bonded above and below it and is bonded to another C atom. The fifth C atom has three H atoms bonded to it.
;

(c) [latex]\text{C}_6\text{H}_{12}[/latex]
This figure shows a C atom with three H atoms bonded to it. This C atom is bonded to another C atom with two H atoms bonded above and below it. The second C atom is also bonded to another C atom down and to the right. This C atom is bonded to one H atom and has a double bond to a fourth C atom. The fourth C atom is also bonded to one H atom. The fourth C atom has a bond up and to the right to another C atom. This C atom has two H atoms bonded above and below it. This C atom also bonds to another C atom which is bonded to three H atoms.
;

(d) [latex]\text{C}_6\text{H}_{12}[/latex]
This figure shows a hydrocarbon chain with a length of five C atoms. The first C atom (from left to right) is bonded to two H atoms and also forms a double bond with the second C atom. The second C atom is bonded to one H atom above it and is also bonded to a third C atom. The third C atom is bonded to two H atoms and also bonded to a fourth C atom. The fourth C atom is bonded to one H atom above it and a C atom below it. The C atom bonded to the fourth C atom in the chain has three H atoms bonded to it. The fourth C atom is also bonded to a fifth C atom which is bonded to three H atoms.
;

(e) [latex]\text{C}_6\text{H}_{10}[/latex]
This figure shows a hydrocarbon chain with a length of six C atoms. The first C atom has three H atoms bonded to it, and it is also bonded to a second C atom. The second C atom has an H atom bonded above and below it. It is also bonded to a third C atom. The third C atom forms a triple bond to a fourth C atom. The fourth C atom forms a single bond with a fifth C atom which has two H atoms bonded above and below it. The sixth C atom has three H atoms bonded to it.
;

(f) [latex]\text{C}_6\text{H}_{10}[/latex]
This figure shows a hydrocarbon chain with a length of five C atoms. The first C atom (from left to right) has three H atoms bonded to it. It is also bonded to a second C atom. The second C atom forms a triple bond to a third C atom. The third C atom forms a single bond with a fourth C atom. The fourth C atom has an H atom bonded above it and a C atom bonded below it. The C atom bonded below the fourth C atom has three H atoms bonded to it. The fourth C atom is bonded to a fifth C atom. The fifth C atom has three H atoms bonded to it.

11. (a) 2,2-dibromobutane; (b) 2-chloro-2-methylpropane; (c) 2-methylbutane; (d) 1-butyne; (e) 4-fluoro-four-methyl-one-octyne; (f) trans-one-chloropropene; (g) 5-methyl-1-pentene

thirteen.
Two structures are shown. The first includes a chain of four singly bonded C atoms. Each C atom has two H atoms bonded above and below it. The two C atoms at either end of the chain each have a third H atom bonded to it. The molecule is named n dash butane. The second includes a chain of three singly bonded C atoms with a C atom bonded above the middle C atom in the chain. The first C atom (from left to right) has three H atoms bonded to it. The second C atom has one H atom bonded below it and a C atom bonded above it. The C atom bonded above the middle C atom has three H atoms bonded to it. The third C atom in the chain has three H atoms bonded to it. This molecule is named 2 dash methylpropane.

15.
This figure includes two structural formulas. The first structure shows two double bounded C atoms with C l bonded to the upper right, C H subscript 3 bonded to the upper left, and H atoms attached to the lower right and lower left in the structure. This structure is labeled cis dash. The second structure shows two double bounded carbon atoms with C l attached to the lower right, C H subscript 3 attached to the upper left, and H atoms attached to the upper right and lower left in the structure. This structure is labeled trans dash.

17. (a) ii,2,4-trimethylpentane; (b) 2,ii,3-trimethylpentane, 2,3,iv-trimethylpentane, and 2,iii,3-trimethylpentane:
Three hydrocarbon molecular structures are shown. The first has C H subscript 3 bonded up and to the right to a C atom. The C atom is bonded down and to the right to C H. C H is bonded up and to the right to C H subscript 2. C H subscript 2 is bonded down and to the right to C H subscript 3. The lone C atom is bonded to two C H subscript 3 groups. The C in the C H group is bonded to a C H subscript 3 group. The second structure shows C H subscript 3 bonded up and to the right to C H which is bonded down and to the right to C H. C H is bonded up and to the right to another C H which is bonded down and to the right to C H subscript 3. The initial C atom is bonded to a C H subscript 3 group. The second C atom is bonded to a C H subscript 3 group. The third C atom is bonded to a C H subscript 3 group. The third structure shows C H subscript 3 bonded up and to the right to C H which is bonded down and to the right to C. C is bonded up and to the right to C H subscript 2 which is bonded down and to the right to C H subscript 3. The second C atom is bonded to a C H subscript 3 group. The third C atom is bonded to two C H subscript 3 groups.

19.
Four structural formulas are provided. The first has a hydrocarbon chain with a length of four C atom. All bonds are single. Nine H atoms are attached and a single C l atom is attached at the far right end of the structure which is labeled 1 dash chlorobutane. The second has a hydrocarbon chain with a length four C atoms. All bonds are single. Nine H atoms are attached and a single C l atom is attached above the second carbon counting left to right. This structure is labeled 2 dash chlorobutane. The third has a hydrocarbon chain with a length of three C atoms. All bonds are single. A single C l atom is bonded beneath the middle C atom and a C H subscript 3 group is also bonded above the middle C atom. Six H atoms are attached, and the structure is labeled 2 dash chloro dash 2 dash methylpropane. The fourth structure has a hydrocarbon chain with a length of three C atoms. All bonds are single. A single C l atom is bonded beneath the first C atom (from left to right) and a C H subscript 3 group is bonded above the middle C atom. Six H atoms are attached, and the structure is labeled 1 dash chloro dash 2 dash methylpropane.

21. In the post-obit, the carbon backbone and the advisable number of hydrogen atoms are shown in condensed form:
Eight structures are shown. The first includes C H subscript 3 bonded to C H subscript 2 bonded to C H subscript 2 bonded to C H subscript 2 bonded to C H subscript 2 with a bond. The second shows C H subscript 3 bonded to C H subscript 2 bonded to C H subscript 2 bonded to C H bonded to C H subscript 3. There is a bond above the fourth C atom (from left to right). The third shows C H subscript 3 bonded to C H subscript 2 bonded to C H bonded to C H subscript 2 bonded to C H subscript 3. There is a bond above the third C atom (from left to right). The five remaining examples involve branching. The fourth structure shows C H subscript 3 bonded to C bonded to C. The second C atom (from left to right) has a bond above it and a bond to an H atom below it. The third C is bonded to two C H subscript 3 groups as well as an H atom. The fifth shows a bond leading to a C H subscript 2 group which is bonded to a C atom. This C atom is bonded to three C H subscript 3 groups. The sixth shows a bond and then C H subscript 2 bonded to C H subscript 2 bonded to C H. The C H is bonded to two C H subscript 3 groups. The seventh shows C H subscript 3 bonded to C H subscript 2 bonded to C with a bond. The C is also bonded to two C H subscript 3 groups. The final structure shows C H subscript 3 bonded to C H subscript 2 bonded to C H. The C H is bonded to a C H subscript 2 group with a bond and a C H subscript 3 group.

23.
Two structural formulas are shown. The first shows two C atoms with a triple bond between them. At each end of the structure, a single H atom is bonded. The second structure involves a hydrocarbon ring of 6 C atoms with a circle at the center. There are alternating double bonds between C atoms. Each C atom is bonded to a single H atom.

In acetylene, the bonding uses sp hybrids on carbon atoms and s orbitals on hydrogen atoms. In benzene, the carbon atoms are sp two hybridized.

25. (a) [latex]\text{CH}\;{\equiv}\;\text{CCH}_2\text{CH}_3\;+\;2\text{I}_2\;{\longrightarrow}\;\text{CHI}_2\text{CI}_2\text{CH}_2\text{CH}_3[/latex]
A reaction is shown. On the left, a four carbon hydrocarbon chain is shown with a triple bond between C atoms 1 and 2 moving left to right across the molecule. The first C is bonded to one H atom. The second C atom bonds with the third C atom. The third C atom is bonded to two H atoms and a fourth C atom. The fourth C atom is bonded to three H atoms. A plus sign is shown followed by 2 I dash I, which is followed by a reaction arrow, then a four C atom hydrocarbon chain with I atoms bonded above and below C atoms 1 and 2 from left to right. The first C atom is bonded to one H. The third C atom is bonded to two H atoms. The fourth C atom is bonded to three H atoms.

(b) [latex]\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_3\;+\;8\text{O}_2\;{\longrightarrow}\;5\text{CO}_2\;+\;half-dozen\text{H}_2\text{O}[/latex]
A reaction is shown. On the left, a five C atom hydrocarbon chain is shown with all single bonds between C atoms. Each C atom is bonded to an H atom above and below it. The two C atoms at either end of the chain each have a third H atom bonded to them. A plus sign is shown followed by 8 O double bond O. To the right of the reaction arrow appears 5 followed by O double bond C double bond O plus 6 O bonded to two H atoms.

27. 65.ii grand

29. nine.328 × 10ii kg


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Source: https://opentextbc.ca/chemistry/chapter/20-1-hydrocarbons/

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