Chapter 4 Alkenes and Alkynes

Multiple Choice
1. Which are the approximate carbon-carbon bond angles at positions I and II in the
following compound?
(Sec. 4.2)

CH3

I
II
a)
b)
c)
d)

109, 109
120, 180
120, 109
109, 120

2. Which is the best description for the indicated bond in the following compound? (Sec.

CH3
4.2)
a)
b)
c)
d)

sp3-sp3
sp3-sp3 and 2p-2p
sp2-sp2 and 2p-2p

sp-sp and sp-sp

3. Which is the IUPAC name for the following structure? (Sec. 4.3)

CH3
H3C

CH CH2

CH2 CH3
a)
b)
c)
d)

3,3-dimethyl-4-pentene
3-methyl-3-ethyl-1-butene
isopropylpentene
3,3-dimethyl-1-pentene

4. Which is the correct structure for vinylcyclobutane? (Sec. 4.3)

CH2
a)

b)

CH2
c)

CH CH2
d)

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Chapter 4 Alkenes and Alkynes

5. Which is the correct name for the following compound? (Sec. 4.3)

CH3
H3C

C
CH2

H
a)
b)
c)
d)

H
C

CH3

2E, 5E-5-methyl-2,5-heptadiene
2E, 5E-3-methyl-2,5-heptadiene
2Z, 5E-3-methyl-2,5-heptadiene
2E, 5Z-5-methyl-2,5-heptadiene

6. Which is the correct name for the following compound? (Sec. 4.3)

CH3

CH3
a)
b)
c)
d)

1,3-dimethylcyclohexene
2,4-dimethylcyclohexene
3,5-dimethylcyclohexene
2,4-dimethyl-1-cyclohexene

7. Which is the correct name for the following compound? (Sec. 4.3)

H3C

CH3
C

H
a)
b)
c)
d)

C
CH2CH3

E-2-ethyl-2-butene
Z-3-methyl-3-pentene
E-3-methyl-2-pentene
Z-3-ethyl-2-butene

8. Which is the IUPAC name for the following compound? (Sec. 4.3)

H3C C
a)
b)
c)
d)

C CH3

dimethyl acetylene
3-butyne
3-butene
2-butyne

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Chapter 4 Alkenes and Alkynes

9. Which is the IUPAC name for the following compound? (Sec. 4.3)

H3C
H3C
CH2CH3
a)
b)
c)
d)

1,1-dimethyl-4-ethyl-2,5-cyclohexadiene
1-ethyl-4,4-dimethyl-2,5-cyclohexadiene
3-ethyl-6,6-dimethyl-1,4-cyclohexadiene
6-ethyl-3,3-dimethyl-1,4-cyclohexadiene

10. Which of the following alkenes do not show cis-trans isomerization? (Sec. 4.3)
I) 2-methyl-2-hexene
II) 1-chloro-1-butene
III) 1-methylcyclohexene
IV) 2-methyl-3-hexene
a)
b)
c)
d)

I, II
III, IV
II, III, IV
I, III

11. Which of the following alkenes show cis-trans isomerization? (Sec. 4.3)
I) 1-chloropropene
II) 3-methylcyclohexene
III) 2,6-dimethyl-2,5-octadiene
IV) 3-ethyl-3-methyl-1-pentene
a)
b)
c)
d)

I, II
II, III
III, IV
I, III

12. How many trans isomers are there for an alkene with the formula, C 4H7Cl? (Sec. 4.3)
a)
b)
c)
d)

2
3
6
8

13. How many cycloalkanes of molecular formula C5H10 show cis-trans isomerism? (Sec. 4.3)
a)
b)
c)
d)

1
2
3
4

38

Chapter 4 Alkenes and Alkynes

14. How many cycloalkanes of molecular formula C6H12 do not show cis-trans isomerization? (Sec. 4.3)
a)
b)
c)
d)

2
3
4
5

15. Arrange the following groups in the order of increasing priority (lowest first). (Sec. 4.3)

CH2CH3

CH2NH2

I
a)
b)
c)
d)

CH2Br

II

CH2OH

III

IV

I, II, IV, III

III, IV, II, I
I, IV, II, III
IV, II, III, I

16. Arrange the following groups in the order of increasing priority (lowest first). (Sec. 4.3)

CH CH2

C CH
II

I
a)
b)
c)
d)

C N

C O
CH3
IV

III

IV, III, II, I

I, II, III, IV
III, IV, I, II
III, I, IV, II

17. Arrange the following groups in the order of increasing priority (lowest first). (Sec. 4.3)

C OCH3

C OH

II

III

a)
b)
c)
d)

O
CH3

C NH2
IV

II, I, IV, III

II, III, I, IV
I, II, IV, III
III, IV, II, I

39

Chapter 4 Alkenes and Alkynes

18. Which structure is Z-2-bromo-3-methyl-2-pentene? (Sec. 4.3)

CH3
H3C

CH2CH3
C

Br

C
CH3

CH CH2CH3

CH3
C

Br

a)

H3C

H3C

Br

C
CH2CH3

b)

Br
C

H3C

CH2CH3

c)

d)

19. Which alkenes have E configurations? (Sec. 4.3)

HO C

Cl
Cl

C OH
C

C
H

H2C

I
a)
b)
c)
d)

CH2Cl

F
C

CH3

H3C

II

C
Cl

III

Br

Cl
C

H3C

C
I

IV

I, II
II, III
III, IV
II, IV

20. How many cis-trans isomers are possible for geraniol? (Sec. 4.3 and 4.5)

CH3
H2C
H2C

C
CH

C
H

CH2OH

C
H3C
a)
b)
c)
d)

CH3

2
3
4
6

21. How many distinct terpene structure types can be made from the assembly of 2-isoprene units? (Sec. 4.5)
a)
b)
c)
d)

1
2
3
4

22. How many isoprene units are there in vitamin A? (Sec. 4.5)

CH2OH

40

Chapter 4 Alkenes and Alkynes

a)
b)
c)
d)

2
3
4
8

23. Cleavage of which of the indicated bonds in limonene leads to a head to tail terpene? (Sec. 4.5)

c)
d)

b)
a)

24. Arrange the following compounds in decreasing order of boiling point (highest first). (Sec. 4.4)

H3C

CH2CH2CH3
I

a)
b)
c)
d)

H3C

CH3
C C CH
CH3
II

CH3
H3C

CH3

III

HC

C C
IV

I, II, IV, III

II, IV, III, I
III, IV, II, I
IV, II, III, I

25. Arrange the following molecules in order of increasing boiling point (lowest first). (Sec. 4.4)

I
a)
b)
c)
d)

II

III

I, II, IV, III

IV, II, III, I
III, IV, II, I
I, II, III, IV

41

IV

CH3

CH3

Chapter 4 Alkenes and Alkynes

Fill in the Blank
1. The IUPAC name of the following molecule is ____________________________________________________.
(Sec. 4.3)

2. The IUPAC name of the following molecule is ____________________________________________________.

(Sec. 4.3)

3. The structure of (3E, 6Z) 2,9-dimethyl-3,6-decadiene is

(Sec. 4.3)
4. The structure of 3,7-diethyl-4,8-dimethyl-1,5-cyclooctadiene is

(Sec. 4.3)
5. The IUPAC name of the following molecule is ____________________________________________________.
(Sec. 4.3)

6. The structure of 2-cyclobutyl-6,6-dimethyl-4-octyne is

42

Chapter 4 Alkenes and Alkynes

(Sec. 4.3)
7. The approximate bond angles of the indicated carbons are 1) ______, 2) _______, 3) _______, 4) ______.
(Sec. 4.2)

3
4

8. The number of isoprene units in menthol is ___________. (Sec. 4.5)

OH

9. The number of isoprene units in grandisol is ____________. (Sec. 4.5)

OH

H
10. The priority order of the groups CH2CH3, -CH3, -OCH3, -CH=CH2 is;

>

>

>
(Sec. 4.3)

43

Chapter 4 Alkenes and Alkynes

True-False
1. The structure of 4-isopropyl-1-methylcyclohexene is

(Sec. 4.3)
2. The name of the following structure is (3E, 5E) 2-ethyl-3,5-octadiene. (Sec. 4.3)

3. The following compounds are listed in order of increasing boiling point (lowest first). (Sec. 4.4)

<

<

<

4. The following groups are listed in order of decreasing priority (highest first). (Sec. 4.3)

CH3
C CH >

CH

>

CH3

C CH2 >
H

CH3

5. The following groups are listed in order of increasing priority (lowest first). (Sec. 4.3)

O
H

<

Cl

<

OCH2CH3

<

Cl

6. The following structures represent identical compounds. (Sec. 4.3)

7. The following structures represent isomers. (Sec. 4.3)

8. 2,2-Dimethylcyclohexene occurs as E and Z isomers. (Sec. 4.3)

9. 2,3-dimethyl-3-hexene occurs as E and Z isomers. (Sec. 4.3)
10. There are 4 possible E,Z isomers of 1,3-pentadiene. (Sec. 4.3)

44

Chapter 4 Alkenes and Alkynes

ANSWERS:

11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.

Multiple Choice
1. c
2. c
3. d
4. d
5. b
6. c
7. c
8. d
9. d
10. d

d
b, two alkenes and a cycloalkane
a
d
a
b
d
c
c
a
c
c
a
a
c

Fill in the Blank

1. (Z) 7-methyl-3-nonene
2. 6,6-dimethyl-1,4-cycloheptadiene

5. 2,8,9-trimethyl-3-decyne

3.
6.

7. 1) 120, 2) 109, 3) 120, 4) 180

4.

8. 2
9. 2

10.

OCH3

>

C CH2 >
H

CH2CH3 >

True-False
1. F
2. F
3. F
4. F
5. T
6. T
7. F
8. F
9. T
10. F

45

CH3