CHAPTER 05

CHAPTER 05
Reactions of Alkenes
Modified and prepared by:
Robert Dominic D. Gonzales
MULTIPLE CHOICE
1. The reaction of propene with which of the following reagents are oxidation reactions?
HBr/CH2Cl2 OsO4 H2/Pt Br2 H+/H2O

I II III IV V
a) II
b) III
c) I and V
d) II and IV
2. Which point on the potential energy diagram represents the intermediate?
B
C
E D
reaction coordinate
CHAPTER 05
3. Which diagram represents the slowest reaction?
E E
reaction coordinate reaction coordinate

A B
E E

C D
4. Which compound has the highest heat (most negative) of hydrogenation?
A B C D
5. Which statement does not describe a transition state?
a) Possesses a definite geometry

b) Maximum on the potential energy diagram
c) Structure can be determined experimentally
d) Can not be isolated
CHAPTER 05
6. Using Markovnikov’s rule, predict the position of the Cl atom in the major product from the reaction of 1-
methylcyclohexene with HCl.
A
C
B D
7. Which species are electrophiles?
OH NH3 H
I II III IV
a) II, III
b) II, IV
c) I, IV
d) I, III
8. Arrange these carbocations in order of increasing stability (least to most).
H3C
I II III IV
a) I, II, III, IV
b) III, I, II, IV
c) II, IV, I, III
d) I, III, IV, II
9. Arrange these carbocations in order of increasing stability (least to most).
I II III
a) I, II, III
b) I, III, II
c) II, I, III
d) III, II, I
CHAPTER 05
10. Which reagents react with an alkene by syn addition?
I. Cl2 II. Br2 III. H2/Pt IV. OsO4/ROOH
a) I, II
b) III, IV
c) II, III
d) I, IV
11. Which reagents react with an alkene by anti addition?

I. Cl2 II. Br2 III. H2/Pt IV. OsO4/ROOH
a) I, II
b) III, IV
c) II, III
d) I, IV
12. Which reagents react with an alkene in a Markovnikov orientation?

I. HBr II. H2O/H2SO4 III. Br2 IV. OsO4/ROOH
a) I, II
b) III, IV
c) II, IV
d) II, III, IV
13. Which is the major product from the reaction of propene with OsO4/ROOH?
a) 1-propanol
b) 2-propanol
c) 1,2-propanediol
d) 1,3-propandiol
14. Which reagents react with an alkene by an electrophilic mechanism?
I. H2O/H2SO4 II. Br2/CCl4 III. HBr IV. H2/Pt
a) I, II, III
b) I, II, IV
c) II, IV
d) III, IV
15. Which is the product of the reaction of 1-methylcyclohexene with H2O/H2SO4?
CH3 CH3 CH3 H

H H
OH OH H CH3
OH OH OH
a) b) c) d)
CHAPTER 05
16. Which is the major product from acid catalyzed hydration of 2-methyl-2-pentene?
a) 2-methyl-3-pentanol
b) 2-methyl-2-pentanol
c) 4-methyl-2-pentanol
d) 3-methyl-3-pentanol
17. Which is the intermediate formed in the reaction of propene with HBr?
Br
Br
a) b) c) d)
18. Which is the major product from the reaction of cyclopentene with Br 2/CCl4?
Br Br
Br H H H
H Br
H Br Br Br
a) b) c) d)
19. Compound A has a molecular formula C8H14 and reacts with H2/Pt to give compound B, C8H16. Which is
compound A?
a) b) c) d)
20. Which is the major product from the reaction of 1,2-dimethylcyclohexene with D2/Pt?
CH3 CH3 D
D
D D CH3 CH3
D CH3 CH3 D
CH3 D D CH3
a) b) c) d)
CHAPTER 05
21. Which alkene has the highest rate of reaction with HBr?
a) b) c) d)
22. Which potential energy diagram represents the reaction of HBr with 2-butene?
E E

A B
E E

C D
23. Which compound does not give two isomers when reacted with Cl 2/CCl4?
a) b) c) d)
24. Which compound has the lowest (least negative) heat of hydrogenation?
a) b) c) d)
CHAPTER 05
25. Which point on the potential energy diagram represents the activation energy?
B
C
E D
reaction coordinate
FILL IN THE BLANK
1. The stereoselective reagents from the following list are _________________________________.
HCl H+/H2O Br2 OsO4 H2
2. Complete the following reaction by providing the major product.
OsO4
CH3COOH
HBr
CH2Cl2
H2
Pt
CHAPTER 05
5. Complete the following reaction by providing the necessary reagents.
Br
Br
6. Complete the following reaction by providing the necessary reagents.
OH
7. Complete the following reaction by providing the starting material and reagents.
Cl
Cl
8. Complete the following reaction by providing the starting materials.

H2
or
Pt
9. Draw the intermediate of the following reaction.
+ HCl
CHAPTER 05
10. Draw the intermediate of the following reaction.
+ Br2
11. Draw the reaction arrows (curved arrows) for the following reaction.
Cl H
Cl
+
+ H Cl C
TRUE-FALSE
C
B
D
A
E
reaction coordinate
1. The reaction represented by the above reaction energy diagram is endothermic.
2. The rate determining step of the reaction represented by the above reaction energy diagram is the first step.
3. The activation energies of the reaction represented by the above reaction energy diagram are noted as A and B.
CHAPTER 05
4. The following carbocations are listed in increasing order of stability (least first).
H
+ H
C CH3 +
+ C
C <
< HC CH3 H
3
5. The following alkenes are listed in decreasing order of heat of hydrogenation (highest first).
> > >
6. The product of the reaction of cyclohexene and bromine is cis-1,2-dibromocycloheane.
7. The major product of the reaction of catalytic hydrogenation of 1,2-dimethylcyclohexene is cis-1,2-

dimethylcyclohexane.
8. Bromination, catalytic hydrogenation, and hydroxylation via osmium tetroxide are cis stereoselective reactions.
9. Hydrohalogenation, hydration, and bromination reactions proceed through an open carbocation intermediate.
10. The reaction arrows (curved arrows) are accurately drawn for the following reaction.
H H Br
+ Br-
H Br
CHAPTER 05
ANSWERS
MULTIPLE CHOICE
1. d
2. c
3. a
4. b
5. c
6. c
7. c
8. b
9. d
10. b
11. a
12. a
13. c
14. a
15. b
16. b
17. d
18. a
19. a
20. b
21. d
22. c
23. a
24. d
25. d
FILL IN THE BLANK

1. Br2, OsO4, H2
2.
OH
OH
3.
Br
4.
H H
CHAPTER 05
5.
Br2
CH2Cl2
6.
H+
H2O
7.
Cl2
CH2Cl2
8.
or
9.
10.
+
Br
11.
Cl H
Cl
+
+ H Cl C
CHAPTER 05
TRUE-FALSE
1. F
2. F
3. T
4. F
5. F
6. F
7. T
8. F
9. F
10. F

CHAPTER 05 - Reactions of Alkenes

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

CHAPTER 05 - Reactions of Alkenes

Uploaded by

Copyright:

Available Formats

HBr/CH2Cl2 OsO4 H2/Pt Br2 H+/H2O

2. Which point on the potential energy diagram represents the intermediate?

3. Which diagram represents the slowest reaction?

reaction coordinate reaction coordinate

reaction coordinate reaction coordinate

4. Which compound has the highest heat (most negative) of hydrogenation?

5. Which statement does not describe a transition state?

a) Possesses a definite geometry

7. Which species are electrophiles?

8. Arrange these carbocations in order of increasing stability (least to most).

10. Which reagents react with an alkene by syn addition?

I. Cl2 II. Br2 III. H2/Pt IV. OsO4/ROOH

11. Which reagents react with an alkene by anti addition?

12. Which reagents react with an alkene in a Markovnikov orientation?

14. Which reagents react with an alkene by an electrophilic mechanism?

I. H2O/H2SO4 II. Br2/CCl4 III. HBr IV. H2/Pt

15. Which is the product of the reaction of 1-methylcyclohexene with H2O/H2SO4?

CH3 CH3 CH3 H

reaction coordinate reaction coordinate

reaction coordinate reaction coordinate

FILL IN THE BLANK

1. The stereoselective reagents from the following list are _________________________________.

HCl H+/H2O Br2 OsO4 H2

2. Complete the following reaction by providing the major product.

3. Complete the following reaction by providing the major product.

4. Complete the following reaction by providing the major product.

5. Complete the following reaction by providing the necessary reagents.

6. Complete the following reaction by providing the necessary reagents.

8. Complete the following reaction by providing the starting materials.

9. Draw the intermediate of the following reaction.

10. Draw the intermediate of the following reaction.

1. The reaction represented by the above reaction energy diagram is endothermic.

> > >

6. The product of the reaction of cyclohexene and bromine is cis-1,2-dibromocycloheane.

7. The major product of the reaction of catalytic hydrogenation of 1,2-dimethylcyclohexene is cis-1,2-

FILL IN THE BLANK

You might also like