Docsity
Docsity

Prepare for your exams
Prepare for your exams

Study with the several resources on Docsity


Earn points to download
Earn points to download

Earn points by helping other students or get them with a premium plan


Guidelines and tips
Guidelines and tips

Selected Answers to Chapter 8: Problems on Organic Compounds - Prof. James C. Armstrong, Assignments of Chemistry

Answers to selected problems in chapter 8 of an organic chemistry textbook, covering topics such as functional groups, alkanes, alkenes, and alkynes.

Typology: Assignments

Pre 2010

Uploaded on 08/19/2009

koofers-user-7ey
koofers-user-7ey 🇺🇸

4.7

(3)

10 documents

1 / 14

Toggle sidebar

This page cannot be seen from the preview

Don't miss anything!

bg1
CHAPTER 8: ANSWERS TO SELECTED PROBLEMS
SAMPLE PROBLEMS (“Try it yourself”)
8.1
8.2
8.3 CH3–CH2–CH2–CH2–CH2–CH3
8.4
8.5 a) This molecule is not an isomer of hexane, because it does not have the same molecular
formula as hexane. Hexane contains six carbon atoms and fourteen hydrogen atoms, but this
molecule contains five carbon atoms and twelve hydrogen atoms.
b) This molecule is an isomer of hexane, because it has the same molecular formula as
hexane, but it has a different structure. Both molecules contain six carbon atoms and fourteen
hydrogen atoms. However, hexane is an unbranched alkane, while this molecule is branched.
8.6 cycloheptane
8.7 4-propyloctane
8.8 4,4-diethyl-3-methylheptane
8.9
H C
H
C
H
C
H
C
H
C
H
H
H
This carbon atom only forms three bonds.
This carbon atom forms five bonds.
H C C C C C C H
H
H
H
H
H
H
H
H
H
H
H
H
CH3CH2CH CH CH2CH2
CH3
CH2CH3
CH2
CH3
pf3
pf4
pf5
pf8
pf9
pfa
pfd
pfe

Partial preview of the text

Download Selected Answers to Chapter 8: Problems on Organic Compounds - Prof. James C. Armstrong and more Assignments Chemistry in PDF only on Docsity!

CHAPTER 8: ANSWERS TO SELECTED PROBLEMS

SAMPLE PROBLEMS (“Try it yourself”)

8.3 CH 3 –CH 2 –CH 2 –CH 2 –CH 2 –CH 3

8.5 a) This molecule is not an isomer of hexane, because it does not have the same molecular

formula as hexane. Hexane contains six carbon atoms and fourteen hydrogen atoms, but this

molecule contains five carbon atoms and twelve hydrogen atoms.

b) This molecule is an isomer of hexane, because it has the same molecular formula as

hexane, but it has a different structure. Both molecules contain six carbon atoms and fourteen

hydrogen atoms. However, hexane is an unbranched alkane, while this molecule is branched.

8.6 cycloheptane

8.7 4-propyloctane

8.8 4,4-diethyl-3-methylheptane

H C H C H C H C H C H H H

This carbon atom only forms three bonds.

This carbon atom forms five bonds.

H C C C C C C H

H

H

H

H

H

H

H

H

H

H

H

H

CH 3 CH 2 CH CH CH 2 CH 2

CH 3

CH 2 CH 3

CH 2

CH 3

8.10 Only propanoic acid contains the same functional group as acetic acid, so propanoic acid

should show similar chemical behavior to acetic acid. The functional group in these two

molecules is:

8.12 2-heptene

(full structural formula) (condensed structural formula)

8.14 cyclooctene

8.15 The double bond in 2-heptene is not at the #1 position, so 2-heptene has cis and trans

forms.

8.16 cis-2-nonene

8.18 These two molecules are structural isomers. When we move the double bond from the

position (in cis-2-hexene) to the #3 position (in trans-3-hexene), we must also move a hydrogen

atom from carbon #3 to carbon #1. This requires breaking a covalent bond.

8.19 The second molecule contains an aromatic ring. The right-hand ring in this molecule

contains six carbon atoms linked by alternating single and double bonds.

C C

F

F F

F

H C C C C C C H

H H

H H

H H

H H

CH 3 CH 2 C C CH 2 CH 3

C C

CH 2

H H

CH 3 CH 2 CH 2 CH 3

OH CH (^) CH 2 O CH 3

alkene

group

alkene

group

C

O

OH

8.5 CH 3 –CH 2 –CH 2 –CH 2 –CH 2 –CH 3

(full structural formula) (Condensed structural formula)

(full structural formula) (Condensed structural formula)

8.10 The central carbon atom makes five bonds in this structure (two bonds to the neighboring

carbon atoms and three to the hydrogen atoms), giving it ten electrons in its valence shell.

Carbon can only share four electron pairs, never five.

Section 8.

8.11 a) linear alkane b) branched alkane c) linear alkane

d) cycloalkane e) branched alkane

H C C C C H

H

H

H

H

H

H

H

H

H C C C C C C C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3

CH 3 CH CH 2 CH CH 3

CH 3 CH 3

H C C C C C H

H

H

H

H

C

H

H

H

H

H

H H

C

H

H H

H C C C C C C

H

H

H

H

H

H

H

H

H

H

C C H

H

H

H

H

H

H

CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3

8.15 a) b)

8.17 a) These two molecules are isomers. Both have the molecular formula (C 6 H 14 ), but they

have different structures.

b) These two molecules are actually the same structure (pentane) drawn in two different

ways, so they are not isomers.

c) These two molecules have different molecular formulas (hexane is C 6 H 14 and

cyclohexane is C 6 H 12 ), so they are not isomers.

Section 8.

8.18 A three-carbon alkyl group is called a propyl group.

8.19 a) 3-methylpentane b) 2-methyloctane

c) 3-ethyl-2-methylheptane d) 2,3-dimethylhexane

e) 2,2,3-trimethylpentane f) 5,5-diethyl-2-methylheptane

g) cyclohexane h) methylcyclopentane

8.20 a) b)

c)

d)

CH 3 CH CH 2 C CH 3

CH 3 CH 3

CH 3 CH 2 CH 2

CH

CH 2

CH 2 CH 2 CH 2 CH 3

CH 3 CH 2 CH 2 CH 2

CH 3

CH 2 CH 3

This carbon atom makes five bonds. CH 3 CH 2 CH 2 CH CH 2 CH 2 CH 3

CH 2 CH 2 CH 3

CH 3 C CH 2 CH 2 CH 3

CH 3

CH 3

CH 3 CH 2 CH CH CH 2 CH 2 CH 2

CH 3 CH 2 CH 2 CH 2 CH 3

CH 2 CH 3

CH CH CH CH CH 2 CH 2 CH 2

CH 3 CH 2 CH 2 CH 2

CH 3 CH 2 CH 3

CH 3 CH 3 CH 3

8.28 a) or b)

c) d)

e) f)

8.31 a) The second carbon from the left is making five bonds, which is not possible. The

correct structure is:

b) Both of the carbon atoms in the alkyne group are making five bonds, which is not

possible. The correct structure is:

Section 8.

8.32 Only 2-pentene has cis and trans forms. Alkenes that have the double bond at the end of

the chain (1-alkenes) do not have cis and trans forms.

8.33 a) trans-3-heptene b) cis-4-octene

8.35 a) These molecules are geometric isomers, because you can interconvert them without

breaking any bonds. Cis and trans forms of the same alkene (3-hexene in this case) are always

geometric isomers.

HC

H 2 C CH 2

CH

CH 3 CH 2 CH CH CH 2 CH 2 CH 2 CH 3

HC C CH 2 CH 2 CH 2 CH 3 HC CH

CH 2 CH CH

CH 3 CH 2

CH 2 CH 2 CH 3 CH 3 C C C CH 2 CH 2 CH 2 CH 3

CH 3

CH 3

CH 3 C

CH 3

CH CH

CH 3

CH 2 CH 2 CH 3

CH 3 C CH CH 3

CH 3

CH C^ CH 3

C C

H

CH 3 CH 2

H

CH 2 CH 2 CH 3

b) These molecules are structural isomers. Whenever you move a double bond from one

position to another (the 3 position to the 2 position in this case), you must also move a hydrogen

atom from one carbon atom to another. This requires breaking a covalent bond.

c) These molecules are structural isomers. The reasoning here is the same as in part b.

d) These molecules are not isomers, because they have different molecular formulas.

Cis-3-hexene is C 6 H 12 , but cyclohexene is C 6 H 10.

Section 8.

8.36 methylbenzene

8.37 ethylbenzene

8.39 Only the middle compound contains an aromatic ring. An aromatic ring must contain

three double bonds, alternating around the ring.

8.40 This molecule contains two alkene groups, an alkyne group, and an aromatic ring.

Section 8.

8.41 The first molecule (benzene) is a liquid and the second is a solid. In general, the larger

the hydrocarbon is, the higher its melting and boiling points will be, because the dispersion force

is stronger for larger molecules.

8.42 Pentane does not contain any oxygen or nitrogen atoms, so it cannot form hydrogen

bonds. Therefore, water is not strongly attracted to pentane. Water molecules prefer to cluster

together, forcing the pentane molecules aside.

8.43 2 C 2 H 2 + 5 O 2 → 4 CO 2 + 2 H 2 O

8.44 These two molecules are both hydrocarbons and are similar sizes, so they should have

similar boiling points.

CH 2 CH 2 CH 3

CH CH C CH alkene alkene alkyne aromatic ring

e) or

f) or

8.65 a) b)

c) d)

e) f)

8.67 a) b)

c) d) or

e) f) or

g) h)

CH 2 CH 2

CH 2

CH 2 CH 2 CH 3

CH 2 CH 2

CH

CH 2

CH 2 CH 2 CH 2 CH 3

CH 3 C C CH 2 CH 2 CH 2 CH 3 C^ C

H

CH 3 H

CH 2 CH 2 CH 3

CH 2 CH 2

CH CH

CH 2

CH 2

CH 2

CH 2 C

CH 3 CH 2 CH 2

CH 2 CH 2 CH 3

CH

CH

CH

CH

CH

CH

CH 3 C C C

CH 3

CH 3

CH 2 CH 3 C C

H

CH 3 CH

H

CH 2 CH 3

CH 3

8.69 a) or

b) c)

8.71 a) pentane b) 3-ethylhexane c) 2,2,7-trimethyloctane

d) 4-ethyl-2,2-dimethylheptane e) cyclopentane

f) methylcycloheptane

8.73 a) 2-pentyne b) trans-2-octene c) 4-methyl-1-pentene

d) 2,5-dimethyl-3-heptyne e) cyclopentene

f) 6-ethyl-7-methyl-cis-3-octene g) ethylbenzene

8.75 a) These two molecules are isomers. Both have the molecular formula C 6 H 14 , but they

have different structures.

b) These two molecules are not isomers, because they have different molecular formulas.

Pentane is C 5 H 12 , but 2-methylpentane is C 6 H 14.

c) These two molecules are not isomers, because they have different molecular formulas.

1-hexene is C 6 H 12 , but cyclohexene is C 6 H 10.

d) These two molecules are isomers. Both have the molecular formula C 6 H 12 , but they

have different structures.

e) These two molecules are isomers. Both have the molecular formula C 7 H 14 , but they

have different structures.

f) These two molecules are isomers. Both have the molecular formula C 7 H 16 , but they

have different structures.

8.77 a) There are seven possible branched molecules that are isomers of 2-methylhexane.

Here are the structures of five of them. The first one is the easiest to find: simply move the

methyl group to a different carbon atom. The others have a shorter principal chain and more (or

longer) branches.

The other two isomers are 3,3-dimethylpentane and 2,4-dimethylpentane.

CH 3 CH 2 CH CH 2 CH 2 CH 3

CH 3

CH 3 C CH 2 CH 2 CH 3

CH 3

CH 3

CH 3 CH CH CH 2 CH 3

CH 3 CH 3

CH 3 CH 2 CH

CH 2 CH 3

CH 2 CH 3 CH 3 C

CH 3

CH 3

CH

CH 3

CH 3

3-methylhexane (^) 2,2-dimethylpentane 2,3-dimethylpentane 3-ethylpentane 2,2,3-trimethylbutane

8.89 Pentane has a higher boiling point than propane. Both compounds are alkanes, but

pentane is a larger molecule than propane, so the dispersion force that attracts pentane molecules

to one another is stronger than the dispersion force between propane molecules.

8.91 Melting points can be affected dramatically by the shape of the molecule, whereas boiling

points of molecules that are the same size are rather similar.

8.93 2 C 6 H 14 + 19 O 2 → 12 CO 2 + 14 H 2 O

8.95 The formula weight of methane (CH 4 ) is 16.042 amu, so the first equation tells us that we

get 213 kcal of heat when we burn 16.042 grams of methane. The formula weight of propane

(C 3 H 8 ) is 44.094 amu, so the second equation tells us that we get 531 kcal of heat when we burn

44.094 grams of propane. We can use these relationships to calculate the amount of heat we get

from 1.00 g of each hydrocarbon:

1.00 g CH 4 ×

213 kcal

16.042 g CH 4

= 13.3 kcal of heat (when you burn 1.00 g CH 4 )

1.00 g C 3 H 8 ×

531 kcal

44.094 g C 3 H 8

= 12.0 kcal of heat (when you burn 1.00 g C 3 H 8 )

As we can see, 1.00 gram of methane produces more heat.

8.97 You have 0.0347 moles of pentane (the calculator answer is 0.03465196 moles). Pentane

has the molecular formula C 5 H 12 and a formula weight of 72.146 amu, so one mole of pentane

weighs 72.146 g. We can use this relationship as a conversion factor:

2.50 g ×

1 mol

72.146 g

= 0.03465196 moles of pentane (calculator answer)

Rounding this answer to three significant figures gives us 0.0347 moles of pentane.

CH 2 CH CH 2

O

O CH 2 C

O

N CH 2 CH 3

CH 2 CH 3

CH 3

Estil

(an anesthetic)

alkene aromatic ring

8.99 Any carbon atom that makes four single bonds will be the center of a tetrahedral

arrangement. In this molecule, there is only one carbon atom that forms four single bonds.

8.101 a) To calculate the density, we must divide the mass by the volume:

65.0 g

75.0 mL

= 0.86666667 g/mL (calculator answer)

This number is valid to three significant figures, so the density of toluene is 0.867 g/mL. The

specific gravity is the same as the density, but without the unit, so the specific gravity of toluene

is 0.867.

b) The toluene will float, because its density is lower than the density of water. (The

density of water is about 1 g/mL.)

8.103 5 ppb equals 5 ng/mL (see page 5-29). There are 1000 mL in one liter, so we can also

express 5 ppb as 5000 ng/L. There are 1,000,000,000 ng (nanograms) in one gram, so we can

write this same concentration as 0.000005 g/L. This last form allows us to compare the safe

concentration to the solubility. For benzene, the solubility (0.6 g/L) is much higher than the safe

concentration (0.000005 g/L). Therefore, benzene in drinking water can be a serious concern,

because the concentration of benzene in drinking water could be far higher than the safe limit.

8.105 Combustion reactions supply most of the energy that we use, either directly (in

automobiles, airplanes, buses, home furnaces, water heaters, etc.) or indirectly (in power plants

that convert the heat of combustion into electrical energy).

CH 2 CH CH 2 C CH