ALKANES AND CYCLOALKANES

PROBLEMS
3
ALKANES

(c) C2C12 (d) cis-l,3-Dichlorocyclobutane

3.1 General
P3.1 Identify the compound with the highest melting point. 3.2 Nomenclature
(a) n-Octane (b) 2,5-Dimethylhexane
P3.7 Write the IUPAC names for each of the following struc-
(c) 2,3,4-Trimethylpentane (d) Bicyclo[2.2.2]octane tures and specify the stereochemistry where required.
P3.2 Identify which compound has the highest boiling point.
(a) n-Pentane (b) Neopentane (2,2-Dimethylpropane) (a) (b)

(c) Isopentane
P3.3 Dodecahedrane is a regular polyhedron consisting of
12 cyclopentane rings (like a football) while eicosane
is a straight-chain compound. Explain the difference in
their melting points of 420° (dodecahedrane) and 37°
(eicosane), even though both are C20 hydrocarbon alkanes.
P3.4 How many constitutional (structural) isomers exist for (c) (d)
the following molecular formulae?
(a) C6H14 (b) C7H16 (c) Dichlorocyclohexane
Cl
(d) C6H12 that have a cyclopropyl ring in their structure
P3.5 How many different kinds (constitutional) hydrogens
are present in the following compounds? (e) (f)

(a) 2,3-Dimethylpentane
F
(b) 2,2,4-Trimethylpentane
(c) 4-Ethyl-3,3,5-trimethylheptane
(d) 2,5,5-Trimethylheptane (g)
(e) 2,4-Dimethylpentane
(f) 3-Ethylpentane
P3.6 The compound with the highest molecular dipole
moment (µ) among the following is: (h)
Cl

(a) Cl (b) Anti conformer of 2,3-dichlorobutane

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 74 CHAPTER 3 ALKANES AND CYCLOALKANES

3.3 Conformational Analysis

(i) (j) Isohexyl iodide P3.10 Represent the following as their Newmann projection:
(a) Most stable conformer of 2-cyclopentyl-6-methylheptane,
looking down the C2 C3 bond.
(b) Gauche conformer of 1-phenylbutane, looking down the
(k) (l) C1 C2 bond.
P3.11 Draw the Newman projections of isopentane and
plot the graph for potential energy vs. rotation about
the C2 C3 bond. Identify the conformer that corre-
sponds to the highest minimum in the plot.
P3.8 Provide the correct IUPAC names for the following
compounds with their bond line structures. P3.12 Why the molecular dipole moment (µ) for FCH2CH2OH
is much larger than that for FCH2CH2F. Use conforma-
(a) 2-Isopropyl-4-methylheptane tional analysis to explain.
(b) 3-(l-Methylbutyl) octane P3.13 The least stable conformation of 3-bromo-2-methyl-
(c) 3-S-Butyl-7-t-butylnonane pentane, viewed through the C-2 C-3 bond (i.e., C-2
in the front, C-3 in the back) is:
(d) Tetraethylmethane
P3.9 Using bond line notation, represent structural formulae
for the following: (a) (b)
(a) Neopentyl alcohol
(b) Isobutyl n-pentyl ether
(c) Allyl bromide
(c) (d)

CYCLOALKANES

(e) Vinylcyclopentane
3.4 General
P3.16 Identify the bicyclic compound with the least strain?
P3.14 How many cis/trans stereoisomers exist for the fol-
lowing?
(a) (b)
(a) Dichlorocyclopentane
(b) Diphenylcyclohexane
(c) 2-Chloro-4-ethyl-l-methylcyclohexane
P3.15 How many different kinds [i.e., constitutional and (c) (d)
geometric (cis/trans)] of hydrogens are there in the
following?
(a) 1-Ethyl-1-methylcyclopropane P3.17 Three structural isomers are possible for methylbi-
cyclo[2.2.1]heptane. One of them has two stereoiso-
(b) Allylcyclobutane
meric forms. Draw structures for all four isomers.
(c) Methylcyclobutane
P3.18 Identify the number of structural isomers that exist for
(d) Chlorocyclopentane methylbicyclo[2.2.2]octane?

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 3.5 NOMENCLATURE 75

P3.19 Identify the more stable stereoisomer in each of the

following pairs, and justify your choice.
(a) cis-or trans-1-Isopropyl-2-methylcyclohexane
(c)
(b) cis-or trans-1-Isopropyl-4-methylcyclohexane
(c) or H3C CH3

CH3

(d) or CH3
H3C
H3C P3.22
CH3
(a) Which of the following has the least negative heat of com-
(e) H3C CH3 or H3C CH3 bustion ( Hcomb)?

CH3 CH3

(f) cis-or trans-1-Isopropyl-3-methylcyclohexane

P3.20 In each of the following groups of compounds, iden-
tify the one with the largest heat of combustion and
the one with the smallest. In which cases can a com-
parison of heats of combustion be used to assess rel-
ative stability?
(a) Cyclopropane, cyclobutane, cyclopentane
(b) cis-1,2-Dimethylcyclopentane, methylcyclohexane,1,1,2,2- (b) Identify the structures in (a) that are the same compound.
tetramethylcyclopropane
(c) 3.5 Nomenclature

H H H P3.23 Give the IUPAC name for each of the following and
specify the stereochemistry where required.
(d)

H H H
(a) (b)
P3.21 State which has the most negative heat of combustion
( Hcomb) in each of (a), (b) or (c)?

(a)
t -Bu t -Bu (c) (d)

(b)

(e)

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 76 CHAPTER 3 ALKANES AND CYCLOALKANES

P3.25 In each of the following, predict whether Keq is

approximately equal to, greater than or less than one:
Ph
(f) (g)

Cl (a) Ph

Ph
Ph

(h) (i)
(b)

(j) (k)
(c)

(l) (m) P3.26 Many alkyl halides undergo loss of HX (dehydroha-

logenation) in the presence of base to form alkenes.
The reaction is known as trans-diaxial elimination
because mechanism generally requires both the leav-
ing proton and halide to occupy axial positions. Based
on this which of the two geometric isomers would
react faster, cis-l-chloro-2-t-butylcyclohexane or
trans-1-chloro-2-t-butylcyclohexane?
P3.27 Explain why the trans-4-fluorocyclohexanol exists
largely in a chair conformation, while its cis-isomer
favours a twist-boat conformation.
(n) (o) P3.28 Two possible configurations of glucose are shown as
follows:

3.6 Conformational Analysis

P3.24 Draw the most stable conformer of

(a) In the structures below, complete the chair conformations

to represent the most stable conformer of (1) and (2).

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 3.6 CONFORMATIONAL ANALYSIS 77

(b) Which configuration would have a more negative heat of and

combustion?
P3.29 One of the chair conformations of cis-l,3-dimethylcy-
clohexane is 5.4 kcal/mol more stable than the other.
If the steric strain of 1,3-diaxial interactions between
hydrogen and methyl is 0.9 kcal/mol, what is the CH3
amount of strain of a 1,3-diaxial interaction between
the two methyl groups? (e) CH3CH2

P3.30 (a) How many cis/trans stereoisomers exist for

1,2,3,4,5,6-hexamethylcyclohexane? and

(b) Draw the conformations for three stereoisomers for which CH3CH2
CH3
Keq = 1 for conformational chair-chair flipping.
CH3
(c) Which is the least stable isomer of those three?
(d) Which stereoisomer would be least likely to undergo (f)
H
conformational flipping?
P3.31 Determine whether the two structures in each of the
following pairs represent constitutional isomers, dif- and
ferent conformations of the same compound, or ste-
reoisomers that cannot be inter-converted by rotation
about single bonds.
CH3
H H
(a) P3.32 Write the structural formula of the most stable confor-
and mation for each of the following compounds
H3C H
CH3 (a) 2,2,5,5-Tetramethylhexane (Newman projection of con-
formation about C3 C4 bond)
CH3
(b) cis-1-Isopropyl-3-methylcyclohexane
H3C H
(b) (c) trans-1-Isopropyl-3-methylcyclohexane
and
H (d) cis-1-tert-Butyl-4-ethylcyclohexane
H3C
CH3 (e) cis-1,1,3,4-Tetramethylcyclohexane
(c) cis-1,2-Dimethylcyclopentane and trans-1,3-dimethylcy- H
clopentane CH3
(f)

(d) H
H3C
H CH3

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 78 CHAPTER 3 ALKANES AND CYCLOALKANES

SOLUTIONS

ALKANES

3.1 General
S3.1 The compound with highest melting point is bicyclo[2.2.2]octane. It is most spherical in shape.

.
S3.2 The compound with highest boiling point is n-pentane. It is straight chain compound.
.
S3.3 Dodecahedrane has higher melting point than eicosane because spherical molecules tend to pack more closely in the solid
state than linear ones, thus requiring more energy to separate (melt) them.

Eicosane, mp 37º

Dodecahedrane, mp 420º

S3.4
(a) The number of constitutional isomers for the molecular formula C6H14 is five.

(b) The number of constitutional isomers for the molecular formula C7H16 is nine.

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 SOLUTIONS 79

(c) The number of constitutional isomers for dichlorocyclohexane is four.

(d) The number of constitutional isomers for C6H12 that contain a cyclopropyl ring is six.

S3.5 Different kinds (constitutional) of hydrogens in the given compounds are as follows:
(a) There are six different kinds of hydrogens present in 2,3-dimethylpentane.

(b) There are four different kinds of hydrogens present in 2,2,4-trimethylpentane.

(c) There are ten different kinds of hydrogens present in 4-ethyl-3,3,5-trimethylheptane

(d) There are seven different kinds of hydrogens present in 2,5,5-trimethylheptane.

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 80 CHAPTER 3 ALKANES AND CYCLOALKANES

(e) There are three different kinds of hydrogens present in 2,4-dimethylpentane.

(f) There are three different kinds of hydrogens present in 3-ethylpentane.

S3.6 Highest molecular dipole moment is observed in cis-1,3-dichlorocyclobutane, as the dipole moment of the two C Cl
bond is not cancelled out.

The dipole moment is zero in case of (a), (b) and (c) because of symmetrical structures of molecules, in which dipole
moment of two C Cl bonds are cancelled out.

3.2 Nomenclature
S3.7 (a)

4-Ethyl-2,2,5-trimethyl-3-nitroheptane
(b)

2,3,7-Trimethyl-4-n-propyloctane (Numbering is started from carbon atom with more branching)

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 SOLUTIONS 81

(c)

5-Ethyl-3,5-dimethyloctane
(d)

5-(2-Chloro-2-methylpropyl)-4-methyldecane
(e) The two possible names for the compound are 4-t-butyl-2, 2, 6-trimethyl-4-n-propylheptane and 4-t-butyl-2,2-dimethyl-
4-(2-methylpropyl)heptane. Since, in case of chains of equal length, the chain with the greater number of substituents are
preferred over lesser number of substituents, hence, the second possible name of the compound is incorrect.

4-Butyl-2,2,6-trimethyl-4-(1,1-dimethylpropyl) heptane.
(f)

4-Fluoro-2-methyl-2-phenylheptane
(g)

5-(1,2-Dimethylpropyl)nonane

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 82 CHAPTER 3 ALKANES AND CYCLOALKANES

(h)

7-Bromo-3-ethyl-2-iodo-5,6-dimethylnonane
(i)

2,3-Dimethyl-4-n-propylnonane
(j)

1-Iodo-4-methylpentane
(k)

4-Ethyl-3,3,5-trimethylheptane
(l)

5-Ethyl-3,4-dimethyloctane
S3.8 The correct IUPAC names for the following compounds are:
(a)

2,3,5-Trimethyloctane

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 SOLUTIONS 83

(b)

5-Ethyl-4-methyldecane
(c)

3,7-Diethyl-2,2,8-trimethyldecane
(d)

Diethylpentane
S3.9 The following are the structural formulae of the given compounds, with bond-line notation:
(a)

(b)

(c)

3.3 Conformational Analysis

S3.10 (a) The compound 2-cyclopentyl-6-methylheptane is most stable when the largest R groups are positioned anti to each
other. Hence, the most stable conformer is

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 84 CHAPTER 3 ALKANES AND CYCLOALKANES

(b) Gauche conformer of 1-phenylbutane implies that the largest R groups are at a dihedral angle of 60° to each other. Hence,
the Newman projection is

S3.11 The Newman projections of isopentane are

The plot for potential energy vs. rotation about C2—C3 bond for these structures is as follows:

Conformer E in which the dihedral angle between both the methyl groups is 60° corresponds to highest minimum in the graph.
S3.12 The dipole moment (μ) of F CH2CH2OH is much larger than FCH2CH2F because an intramolecular hydrogen
bonding between highly electronegative F and H of ( OH) leads to stabilization of a gauche conformer of FCH-
2CH2OH thereby adding to the net dipole moment in the same direction. On the other hand, the net dipole moment in
FCH2CH2F is zero because of oppositively oriented F atoms.

S3.13 Eclipsed conformation is least stable. Steric repulsion between the molecules raises the energy of the conformation
which makes the molecule less stable. Thus, the correct option is (c).
CYCLOALKANES

3.4 General
S3.14
(a) The number of cis/trans stereoisomers for dichlorocyclopentane is two pairs.

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 SOLUTIONS 85

(b) The number of cis/trans stereoisomers for diphenylcyclohexane is three pairs

.
(c) The number of cis/trans stereoisomers for 2-chloro-4-ethyl-l-methylcyclohexane is four pairs.

S3.15
(a) Different kinds of constitutional and geometric hydrogens in 1-ethyl-1-methylcyclopropane are five.

(b) Different kinds of constitutional and geometric hydrogens in allylcyclobutane are nine.

(c) Different kinds of constitutional and geometric hydrogens in methylcyclobutane are six.

Note: H1and H2 are cis and trans to methyl and so are counted as different.

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 86 CHAPTER 3 ALKANES AND CYCLOALKANES

(d) Different kinds of constitutional and geometric hydrogens in chlorocyclopentane are five.

(e) Different kinds of constitutional and geometric hydrogens in vinylcyclopentane are eight.

S3.16 In the given compounds, the least strained bicyclic compound is (a) because the trans isomer shows no strain.

In (b), the cis isomer shows diaxial strain.

In (c), ring strain prevents alkene from being planar and Bredt’s rule is violated.

In (d), angle strain is observed.

S3.17 The structure of four isomers of methylbicyclo[2.2.1]heptane are:

(1) (2) (3) (4)

The structures (3) and (4) are stereoisomers.

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 SOLUTIONS 87

S3.18 The number of structural isomers for methylbicyclo[2.2.2]octane are two.

(1) (2) (3) (4)

Compounds (2), (3) and (4) represent identical structures.
S3.19 (a) The axial methyl group in the cis stereoisomer of 1-isopropyl-2-methylcyclohexane faces unfavourable repulsion
with axial hydrogens at C-4 and C-6 which make it less stable than its corresponding trans-isomer where the methyl
group is in equatorial position and diaxial interactions are minimized.

(b) The most stable stereoisomer is trans-1-isopropyl-4-methylcyclohexane due to both alkyl groups being at equatorial posi-
tion. In cis isomer, axial methyl group is involved in repulsion with axial H at C-2 and C-6, thereby leading to a less stable
isomer than trans.

(c) The first stereoisomer of 1,2,4-trimethylcyclohexane is the more stable one because all its methyl groups are equatorial, but
one of the methyl groups is axial in the most stable conformation of the second stereoisomer

(d) Each stereoisomer of 2,3-dimethylbicyclo[3.2.1]octane has one axial and one equatorial methyl group. The first one, how-
ever, has a close contact between its axial methyl group and both methylene groups of the two-carbon bridge leading to
more Van der Waal strain and loss of stability. The second stereoisomer has repulsions with only one axial methylene
group; lesser Van der Waal strain and therefore it is more stable.

(e) The first stereoisomer of 1,2,4-trimethylcyclohexane is the more stable one. All its methyl groups are equatorial in its most
stable conformation. The most stable conformation of the second stereoisomer has one axial and two equatorial methyl groups.

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 88 CHAPTER 3 ALKANES AND CYCLOALKANES

(f) The more stable stereoisomer is cis-1-isopropyl-3-methylcyclohexane because both the alkyl groups are equatorial.
The trans isomer is less stable because axial methyl group is involved in repulsion with axial H at C-1 and C-5.

S3.20
(a) The heat of combustion is highest for the hydrocarbon with the greatest number of carbons. Thus, cyclopropane has the
lowest heat of combustion even though it is more strained than cyclobutane or cyclopentane.

A comparison of heats of combustion can only be used to assess relative stability when the compounds are isomers. Hence,
for the given compounds comparison of stability cannot be made.
(b) All these compounds are isomers with molecular formula C7H14. Hence, their heats of combustion can be compared on
the basis of relative stability of isomers. Therefore, the one with the most strain will have the highest heat of combustion.

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 SOLUTIONS 89

(c) All these hydrocarbons have different molecular formulae. Their heats of combustion decrease with decreasing number of
carbons, and comparisons of relative stability cannot be made.

(d) Since, bicyclo[3.3.0]octane and bicyclo[5.1.0]octane are isomers, their heats of combustion can be compared on the basis
of their relative stabilities. The third hydrocarbon, bicyclo[4.3.0]nonane, has a greater number of carbons than either of the
other two and hence the largest heat of combustion. The three-membered ring in bicyclo[5.1.0]octane imparts a significant
amount of angle strain to this isomer, making it less stable than bicyclo[3.3.0]octane.

S3.21 The compound with the most strain is the least stable and has the most negative ΔHcomb.
(a) The isomer (ii) is the least stable; therefore, has most negative ΔHcomb.

(i) (ii) (iii)

(b)

(i) (ii) (iii)

The isomer (ii) is the least stable due to dimethyl repulsion therefore, has most negative ΔHcomb.
(c) The isomer (i) is the least stable and has the most negative ΔHcomb.

(i) (ii) (iii)

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 90 CHAPTER 3 ALKANES AND CYCLOALKANES

S3.22 The compound that is most stable (least strain) will have the least negative ΔHcomb.
(a)

(i) (ii) (iii)

In (ii) all alkyl groups are equatorial; therefore, most stable.
Compounds (iii) and (iv) are the same.

3.5 Nomenclature
S3.23

(a)

1-Bromo-6-t-butyl-3-vinylcyclooctane or 1-Bromo-6-(1,1-dimethyl ethyl)-3-ethenyl cyclooctane

(b)

cis-1-Isopentyl-5-n-propylcyclodecane or cis-1-(3-Methyl butyl)-5-propylcyclodecane

(c)

1-Ethyl-4-(1-methylpropyl)-2-propyl cyclohexane

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 SOLUTIONS 91

(d)

l-Cyclopropyl-3-methylbutane

(e)

4-(2-Cyclohexylethyl)-3-methylheptane

(f)

t-Pentylcyclopentane or 1,1-dimethylpropyl cyclopentane

(g)

trans-1-Chloro-2-s-butylcyclopentane or trans-1-Chloro-2(1-methylpropyl) cyclopentane

(h)

(2-Fluoro-1-methylbutyl)cycloheptane

(i)

trans-1-(2,3-Dimethylbutyl)-2-n-propylcycloheptane

(j)

trans-1-Chloro-3-phenylcyclohexane

(k)

cis-1-Allyl-2-isobutylcyclohexane or cis-1-(2'-Methylpropyl)-2-prop-2-enyl-cyclohexane

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 92 CHAPTER 3 ALKANES AND CYCLOALKANES

(l)

3-(1-Cyclobutylethyl)-6-ethyl-5-iodo-2,2,8,8-tetramethylnonane
(m)

2,6,6-Trimethylbicyclo[3.1.1]heptane
(n)

2,9,9-Trimethylbicyclo[5.2.0]nonane
(o)

4-(1,1-Dimethylethyl)-2-methyl-5-phenylheptane

3.6 Conformational Analysis

S3.24 Most stable conformer for menthol and neomenthol are:

Menthol Neomenthol

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 SOLUTIONS 93

S3.25
(a) The two structures are degenerate structures (same energy); therefore, Keq = 1

(b) In the flipped conformation (ii) 1,3-diaxial interactions are more, so it is less stable conformer; therefore, Keq< 1

(i) (ii)
(c) In the flipped conformation (ii) larger ethyl group is more stable in the equatorial position; therefore, Keq> 1

(i) (ii)
S3.26 In the trans isomer, both tert-butyl and Cl occupy equatorial positions. Bulky tert-butyl group prevents flipping of chair
conformer, therefore, Cl cannot assume axial position in trans isomer. Whereas in cis isomer, Cl is already in axial posi-
tion thus 1,3-diaxial elimination occurs easily in the presence of a base. Therefore, cis-isomer would react more rapidly.

S3.27 The twist-boat conformation of cis-isomer is stabilized by intramolecular hydrogen bonding; which is not possible in
chair conformer (or in trans-isomer). Hence, boat conformer is preferred conformation for cis-isomer due to additional
stabilization.

S3.28
(a)

(b) Configuration (2) is less stable as one substituent is axial and hence would have more negative ΔHcomb.

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 94 CHAPTER 3 ALKANES AND CYCLOALKANES

S3.29 Structure (i) is less stable than (ii) by 5.4 kcal/mol due to the presence of 1,3-diaxial repulsion. In first structure: Two
1,3-diaxial interaction is present between methyl and hydrogen so, total steric strain is 0.9 × 2 = 1.8 kcal/mol. In the
second structure methyl-methyl 1,3-diaxial interaction is present whose value is 5.4 − 1.8 = 3.6 kcal/mol

S3.30
(a) The number of cis/trans stereoisomers that exist for 1,2,3,4,5,6-hexamethylcyclohexane is eight.

(b) For conformational chair-chair flipping, Keq= 1 for configurations (i), (iii), and (v) which have equal number of equatorial
and axial groups (3e/3a).

(c) The least stable isomer is (i) because, three 1,3-diaxial steric interactions exist between two methyl groups, whereas only one
such interaction exists in configurations (iii) and (v).

(d) The stereoisomer which is least likely to flip is (viii), because all methyl groups that are equatorial will become axial (less
stable).

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 SOLUTIONS 95

S3.31
(a) By rewriting the structures in a form that shows the order of their atomic connections, it is apparent that the two structures
are constitutional isomers that is 2,2-dimethylpropane and 2-methylbutane.

(b) The two compounds have the same constitution: (CH3)2CHCH(CH3)2. The Newman projections represent different stag-
gered conformations of the molecule 2,3-dimethylbutane. In the first structure the hydrogens at C-2 and C-3 are anti to each
other, whereas in the second structure they are gauche.

(c) The compounds differ in the order in which the atoms are connected, so they are constitutional isomers of dimethyl cyclo-
pentane. Although the compounds have different stereochemistry (one is cis, the other trans), they are not stereoisomers
because they have different constitution.

(d) Both structures are cis-1-ethyl-4-methylcyclohexane. In the first structure the methyl is axial and the ethyl equatorial. The
orientations are opposite to these in the second structure. The two structures are ring-flipped forms of each other hence
different conformations of the same compound.

and

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 96 CHAPTER 3 ALKANES AND CYCLOALKANES

(e) The methyl and the ethyl groups are cis (both ethyl and methyl groups are up) in the first structure but trans (ethyl group is
down, methyl group is up) in the second. The two compounds are stereoisomers; they have same constitution but differ in
the arrangement of their atoms in space.

(f) The two structures have the same constitution but differ in the arrangement of their atoms in space hence, they are stereo-
isomers. They are not different conformations of the same compound, because they are not related by rotation about C–C
bonds. In the first structure shown below the methyl group is trans to the bonds marked with arrows, whereas in the second
structure it is cis to these bonds.

S3.32
(a) The structural formula of 2,2,5,5-tetramethylhexane is (CH3)3CCH2CH2C(CH3)3. The most stable conformation is achieved
when the large tert-butyl groups lie anti to each other.

(b) An isopropyl group is bulkier than a methyl group and will have a greater preference for an equatorial orientation in the
most stable conformation of cis-1-isopropyl-3-methylcyclohexane. Both substituents are equatorial in the most stable con-
formation of cis-1-isopropyl-3-methylcyclohexane.

(c) The bulkier isopropyl group is equatorial and the methyl group axial in the most stable conformation.

(d) In a cyclohexane ring for two substituents located at position 1 and 4, to be cis to each other, one substituent must be axial
and the other equatorial.

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 SOLUTIONS 97

To achieve the most stable conformation, we place the larger substituent (the tert-butyl group) at the equatorial site and the
smaller substituent (the ethyl group) at the axial one

(e) In the more stable chair conformation: C-3 methyl group is equatorial with no Van der Waals strain between axial C-1
methyl group and C-3 methyl group. In the less stable chair conformation: C-3 methyl group is axial with strong Van der
Waals strain between axial C-1 and C-3 methyl groups.

(f) To arrive at the most stable conformation, first draw the projection formula as a chair conformation and then write its ring-
flipped form.

The first conformation with two axial methyl groups is less stable and the second conformation with one axial group is
more stable.

The ring-flipped form, with two equatorial groups and one axial methyl group, is more stable than the originally drawn
conformation, with two axial groups and one equatorial methyl group. This is because in less stable conformation, both CH3
placed are axially to each other which will undergo repulsion with axially placed hydrogens. For example,
Methyl group at C1 will undergo repulsion with H at C3 and C5.
Methyl group at C2 will undergo repulsion with H at C4 and C6.
In ring flipped conformation, there is only one axial CH3 group. Therefore, diaxial repulsions are reduced than previous
case. Hence, it is more stable conformer of the two.

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