ALKANES AND

CYCLOALKANES

2-1 What is the molecular formula of the alkane represented by the carbon skeleton
shown?

1. C13H22

2. C13H24

3. C13H26

4. C13H28

5. C13H30

2-2 What is the correct IUPAC name for the alkane given in problem 2-1?

1. 2-Propyl-3-ethyl-6-methylheptane 4. 4,7-Dimethyl-5-ethylnonane
2. 3-Ethyl-6-methyl-2-propylheptane 5. 5-Ethyl-2,6-dimethylnonane
3. 2-Methyl-5-ethyl-6-methylnonane

2-3 How many primary carbons are present in the alkane shown?

1. 1 4. 4

2. 2 5. 5

3. 3
2-4 How many secondary carbons are present in the alkane shown?

1
 1. 1 4. 4

2. 2 5. 5

3. 3

2-5 How many tertiary carbons are present in the alkane shown?

1. 1 4. 4

2. 2 5. 5

3. 3

2-6 Which of the following is an isomer of the compound shown?

1. 2-Methylheptane 3. 2,2,3,4-
Tetramethylpentane
2. 2,5-Dimethylhexane
4. 2,5-
Dimethylcycloheptane

2-7 Which one of the following compounds is an isomer of octane?

1. n-Octane 4. 2-Methylheptane
2. Cyclobutylcyclobutane 5. 2-Methyloctane
3. Cyclooctane

2-8 Which pair of compounds are constitutional isomers?

1. Butane and Cyclobutane 3. 3-Methylpentane and 3-

Methylhexane
2. Cyclopentane and Methylcyclopentane 4. 2-Methylpentane and 2,3-
Dimethylbutane

2-9 How many constitutional isomers of C 9H20 have 8 carbons in their longest
continuous chain?

1. 1 2. 2 3. 3 4. 4 5. 5

2-10 How many constitutional isomers of C 10H22 have 9 carbons in their longest
continuous chain?

1. 1 2. 2 3. 3 4. 4 5. 5

2
2-11 How many constitutional isomers of C 10H22 are named 2,x-dimethyloctane?

1. 1 2. 2 3. 4 4. 6 5. 7

2-12 Only one of the following compounds is named correctly according to the IUPAC
rules. Which one?

Structural formula Proposed name

1. 3,3,5,6-Tetramethylheptane

2. 2,5,6-Trimethyloctane

3. 4-Pentylheptane

4. CH2CH(CH3)2 tert-Butylcyclopentane

2-13 What is the IUPAC name of the compound shown below?

CH3

CH3CH2CH2CHCH2C CH3

CH3 CH2CH3

1. 4,6-Dimethyl-6-ethylheptane 4. Isooctane
2. 2,4-Dimethyl-2-ethylheptane 5. 4,6-Dimethyl-6-isobutylpentane
3. 3,3,5-Trimethyloctane

2-14 The IUPAC name of the alkane shown below is:

CH3

CH3CH2CHCH2CH CH CH3
CH3 CH2CH2CH3

1. 4-Isopropyl-6-methyloctane
2. 5-Isopropyl-3-methyloctane

3
3. 3,6-Dimethyl-5-propylheptane
4. 2,5-Dimethyl-3-propylheptane
5. 2-Ethyl-4-isopropylheptane

4
2-15 The correct IUPAC name for the following compound is:
CH2CH3

CH3CH2CH2CH2CHCH2CH2CHCH3

CH2

CH
CH3 CH3

1. 2-Ethyl-5-isobutylnonane
2. 5-sec-Butyl-2-ethylnonane
3. 6-sec-Butyl-3-methylnonane
4. 4-Butyl-2,7-dimethylnonane
5. 6-Isobutyl-3-methyldecane

5
 CH3CHCH2CH3
2-16 The group is called:

1. Butyl 3. Isobutyl
2. sec-Butyl 4. tert-Butyl

2-17 Another name for a sec-butyl group is:

1. 1-Methylpropyl 3. Isobutyl
2. 2-Methylpropyl 4. 1,1-Dimethylethyl

2-18 Another name for a tert-butyl group is:

1. 1-Methylpropyl 3. Isobutyl
2. 2-Methylpropyl 4. 1,1-Dimethylethyl

2-19 Which one of the following is isobutylcyclopentane?

CH2CH2CH2CH3 CH2CHCH3

CH3

1. 2. 3.

CHCH2CH3 C(CH3)3

CH3
4. 5.

6
2-20 What is the correct IUPAC name of the alkyl group shown?
CH2CH3
CHCH2CHCH3

CH3

1. 1-Ethyl-3-methylbutyl
2. 1-Ethyl-3,3-dimethylpropyl
3. 2-Methyl-4-ethylbutyl
4. 5-Methylhexyl
5. 1-Isopropyl-sec-butyl

2-21 The IUPAC name of the alkane shown is:

1. 2-Isopropylbutane 4. 2,3-Dimethylpentane CH(CH3)2

H H

H CH3
CH3

2. 2-Methyl-2-isopropylpropane 5. 1,1,2,3-Tetramethylpropane
3. 1,2-Dimethyl-1-isopropylethane

2-22 The IUPAC name of the alkane shown is:

CH3

H H

CH3 CH3
C(CH3)3
1. 1,1,1,3,3,3-Hexamethylpropane
2. 1,2-di-tert-Butylethane
3. 1-tert-Butyl-2,2-Dimethylpropane
4. 2,2,4,4-Tetramethylpentane
5. 2-tert-Butyl-1,1,1-Trimethylethane

2-23 Which is the Newman projection of the gauche conformation of butane?

 CH3 CH3 CH3 CH3
CH3CH3 H
H CH3 H H H H CH3
H H H
H H H CH3 H CH3
H H CH3
H H H H

1. 2. 3. 4. 5.

2-24 Which is the Newman projection of the anti conformation of butane?

CH3 CH3 CH3 CH3

CH3CH3 H
H CH3 H H H H CH3
H H H
H H H CH3 H CH3
H H CH3
H H H H

1. 2. 3. 4. 5.

2-25 Which one of the following is a Newman projection of 2,2-dimethylpropane?

CH3 CH3 CH3 H CH3

H CH3 H H CH3 CH3 CH3 CH3 H H

H CH3 H CH3 CH3 CH3 H CH3 CH3

H H CH3
H CH3 H

1. 2. 3. 4. 5.

2-26 In which two of the following are the methyl group and the chlorine anti to one
another?

Cl Cl H H

H H H H Cl H H Cl
H CH3 H H H CH3 H H

H CH3 H CH3
A B C D
1. A and B 4. B and C
2. A and C 5. B and D
3. A and D

2-27 In which two of the following are the methyl group and the chlorine gauche to
one another?
 Cl Cl H H

H H H H Cl H H Cl
H CH3 H H H CH3 H H

H CH3 H CH3
A B C D
1. A and B 4. B and C
2. A and C 5. B and D
3. A and D

2-28 Identify the atom that is anti to A.

1. X
2. B
3. C
4. D
5. E
A
E
B
X
C

2-29 Identify the atom that is anti to X.

1. A
2. B
3. C
4. D
5. E
A
E
B
X
C

2-30 The molecular model shown is a staggered conformation of CH 3CH2CH2Br. What

term best describes the atom that is anti to bromine?
 1. a primary carbon
2. a primary hydrogen
3. a secondary carbon
4. a secondary hydrogen
5. a tertiary hydrogen

2-31 What atom is gauche to X?

2-32 Which statement is true about the compound Cl

shown at the right? CH3
Br

1. Br, Cl, and CH3 are cis to each other

2. Br is trans to Cl, and cis to CH 3

3. Br is cis to Cl, and trans to CH 3

4. Br is trans to both Cl and CH 3

2-33 Which statement is true about the compound Cl

shown at the right? CH3
Br

A. Br is gauche only to Cl

B. Br is gauche to both Cl and CH3

C. Br is anti to both Cl and CH3

D. Br is gauche to Cl, and anti to CH 3

 E. Br is anti only to Cl

2-34 Specify the relationship between the pair of compounds shown :

H Cl H H

Cl H Cl Cl

1. Different representations of same compound 4. Stereoisomers

2. Different conformations of same compound 5. Resonance forms
3. Constitutional isomers
2-35 myo-Inositol has the structure shown. What is the relationship of compound X to
myo-inositol?
OH
OH
HO OH HO
OH
OH
HO OH OH
OH
OH
myo-Inositol Compound X

1. Compound X is myo-inositol shown in its most stable conformation.

2. Compound X is myo-inositol shown in its least stable conformation.

3. Compound X is a resonance form of myo-inositol.

4. Compound X is a constitutional isomer of myo-inositol.

5. Compound X is a stereoisomer of myo-inositol.

2-36 Which one of the following structures corresponds to the most stable
conformation of cis-1-tert-butyl-4-methylcyclohexane?

C(CH3)3 CH3 C(CH3)3

H H H
H (CH3)3C H3C

CH3 H H
1. 2. 3.
H H

CH3 H3C
(CH3)3C C(CH3)3

H H
4. 5.

2-37 The most stable chair conformation of trans-1-tert-butyl-3-methylcyclohexane is

the one in which
1. the tert-butyl group is axial and the methyl group is equatorial.
2. the methyl group is axial and the tert-butyl group is equatorial.
3. both groups are axial.
4. both groups are equatorial.

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2-38 The most stable chair conformation of cis-1-tert-butyl-3-methylcyclohexane is the
one in which
1. the tert-butyl group is axial and the methyl group is equatorial.
2. the methyl group is axial and the tert-butyl group is equatorial.
3. both groups are axial.
4. both groups are equatorial.

2-39 Methyl groups are cis to each other in which of the following?

CH3 CH3 H

H H CH3
CH3 H CH3

H CH3 H

A B C
1. only A 4. A and B
2. only B 5. A and C
3. only C

2-40 Which pair of structures below are interconvertible by ring-flips?

CH3 CH3 H

H H CH3
H3C H H3C

H CH3 H

A B C

1. A and B 4. All of them

2. A and C 5. None of them
3. B and C

2-41 Which one of the following compounds is a constitutional isomer of

cis- 1,2-dimethylcyclobutane?

1. cis-1,2-Dimethylcyclopropane 4. trans-1,2-Dimethylcyclobutane
2. trans-1,2-Dimethylcyclopropane 5. 2,2-Dimethylbutane
3. 1,1-Dimethylcyclobutane

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2-42 Which one of the following compounds is a stereoisomer of
cis- 1,2-dimethylcyclopentane?

1. Methylcyclohexane 4. cis-1,3-Dimethylcyclopentane
2. 1,1-Dimethylcyclopentane 5. trans-1,3-Dimethylcyclopentane
3. trans-1,2-Dimethylcyclopentane
2-43 Which two compounds given below are isomers?

A B C D E

1. A and B 4. D and E
2. B and C 5. none are isomers
3. C and E

CH3 CH3 H
CH3
H H CH3
CH3 CH3
H
H H

2-44 What is the relationship between the two structures shown?

1. Stereoisomers
2. Constitutional
isomers
3. Equivalent structures
4. Different conformations of same compound
2-45 Which structural formula is the most stable?

CH3 CH3
CH3 CH3 CH3
CH3 CH3
CH3 CH3
1. 2. 3.

14
 CH3
CH3 CH3

CH3
CH3 CH3
4. 5.

2-46 In which structural formula are all of the methyl groups cis to one another?

CH3 CH3
CH3 CH3 CH3
CH3 CH3
CH3 CH3
1. 2. 3.
CH3
CH3 CH3

CH3
CH3 CH3
4. 5.

2-47 The most stable conformation of the compound shown (all methyl groups are cis
to one another) has:

1. all methyl groups axial.

2. all methyl groups equatorial.
3. equatorial methyl groups at C-1 and C-2.
4. equatorial methyl groups at C-1 and C-4.
5. equatorial methyl groups at C-2 and C-4.

1 CH3

CH3 4 2 CH3

2-48 Which one of the following is the most stable conformation of the compound it
represents?

15
 H CH3
CH3
HO H H H3C H
H H CH3
H CH3
C(CH3)3 H H

1. 2. 3. 4.

16