ALKENE

1.

What is the approximate value of the C-C-C bond angle in propene?

a.
90
b.
109
c.
120
d.
180

2.

What is the hybridization of carbon atoms labeled i iii in the following structure?
H

H2C
i

a.
b.
c.
d.

C
ii

CH3
iii

i = sp2; ii = sp2; iii = sp2

i = sp; ii = sp; iii = sp3
i = sp2; ii = sp; iii = sp3
i = sp2; ii = sp2; iii = sp3

3.

What is the approximate value of the C-C-C bond angle in propene?

a.
90
b.
109
c.
120
d.
180

4.

What is the IUPAC name of the following compound?

a.
b.
c.
d.
5.

What is the IUPAC name of the following compound?

a.
b.
c.
d.
6.

2-methylenepentane
2-methyl-1-pentene
2-vinylpentane
2-propyl-1-propene

(E)-3-methyl-4-hexene
(Z)-3-methyl-4-hexene
(E)-4-methyl-2-hexene
(Z)-4-methyl-2-hexene

What is the IUPAC name of the following compound?

a.
b.
c.
d.
7.

What is the IUPAC name of the following compound?

a.
b.
c.
d.
8.

2-methyl-4-vinyl-2-pentene
3,5-dimethyl-1,4-hexadiene
2,4-dimethyl-3,5-hexadiene
1,1,3-trimethyl-1,4-pentadiene

(Z)-3-ethyl-5-methyl-1,4-heptadiene
(E)-3-ethyl-5-methyl-1,4-heptadiene
(E)-3-methyl-5-vinyl-3-heptene
(Z)-1,3-diethyl-1-methyl-1,4-pentadiene

How many alkenes have the formula C6H12?

a.
9
b.
10
c.
14
d.
17

9.

What is the major organic product obtained from the following reaction?
H2 O
H2SO4

HO
OH
OH
1

a.
b.
c.
d.
10.

OH
2

1
2
3
4

What is the major organic product obtained from the following reaction?
O

O
+
H

1. OsO4

OH
2

2. NaHSO3
H2O
OH
3

OH

OH

a.
b.
c.
d.
11.

1
2
3
4

What is the major organic product obtained from the following reaction?

CH3

HO

HO

CH3

CH3

H3C

OH

OH
O

OH

1. OsO4
CH3

2. NaHSO3
H2O

a.
b.
c.
d.
12.

1
2
3
4

What is the major organic product obtained from the following reaction?

CH3

HO

HO

CH3

CH3

OH

H3C

OH
O

OH

1. O3

H
CH3

2. (CH3)2S

O
1

a.
b.
c.
d.
13.

1
2
3
4

What is (are) the major organic product(s) obtained from the following reaction?
CH3

CH3

CH3
CH3

CH3

CH3
CH3

CH3

H2
Pt

a.
b.
c.
d.

14.

only 1
only 2
only 3
only 2 and 3

What is (are) the major organic product(s) obtained from the following reaction?

Br2

1 2,3-dibromobutane
2 2,2-dibromobutane
3 3,3-dibromobutane
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2
15.

What is (are) the major organic product(s) obtained from the following reaction?
Br2

1 2,3-dibromobutane
2 2,2-dibromobutane
3 3,3-dibromobutane
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2
16.

What is (are) the major organic product(s) obtained from the following reaction?
1. OsO4

2. NaHSO3
H2O

1 2,3-butanediol
2 2,2-butanediol
3 3 ,3-butanediol
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2
17.

What is (are) the major organic product(s) obtained from the following reaction?
1. OsO4
2. NaHSO3
H2O

1 2,3-butanediol
2 2,2-butanediol
3 3 ,3-butanediol
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2

18.

What is the major organic product obtained from the following reaction?

H2O
H2SO4

OH

OH
OH

OH
2

19.

a.

b.
c.
d.

2
3
4

What is the best choice of reagent(s) to perform the following transformation?

OH
?
OH

a.
b.
c.
d.
20.

H2O, H2SO4
H2SO4
O2
OsO4; followed by NaHSO3

What is the best choice of reagent(s) to perform the following transformation?

O

a.
b.
c.
d.
21.

O3; followed by (CH3)2S

CH3COOOH
O2
OsO4; followed by NaHSO3
What is the best choice of reagent(s) to perform the following transformation?
?

OH

a.
b.
c.
d.
22.

H2O, H2SO4
H2SO4
O2
OsO4; followed by NaHSO3

What type of reactive intermediate is formed in the reaction of an alkene with HBr to
give a bromoalkane?
a.
carbocation
b.
carbanion
c.
radical
d.
cyclic bromonium ion

23.

What type of reaction mechanism accounts for the reaction of an alkene with
aqueous acid to give an alcohol?
a.
nucleophilic addition
b.
electrophilic addition
c.
radical addition
d.
elimination

24.

What type of carbocation is shown?

a.
b.
c.
d.
25.

primary
secondary
tertiary
quaternary

What is the major organic product obtained from the following reaction?
HBr

Br
Br
Br
1

a.
b.
c.
d.
26.

1
2
3
4

What is the correct order of stability of the following carbocations (more stable > less
stable)?

a.
b.
c.
d.
27

Br

1>2>3
1>3>2
3>1>2
3>2>1

What is (are) the major organic product(s) obtained from the following reaction?
HBr

1 (R)-2-bromo-3-methylbutane
2 (S)-2-bromo-3-methylbutane

3 2-bromo-2-methylbutane
a.
only 1
b.
only 2
c.
only 3
d.
only 1 and 2
28.

Which of the following concepts explains Markovnikovs rule as applied to the

addition of HBr to propene?
a.
the relative stability of carbocations
b.
the nucleophilicity of bromide anion
c.
the acidity of HBr
d.
the Aufbau principle

29.

What is the major probuct obtained upon addition of Br2 to (R)-4-tertbutylcyclohexane?

a.
(1R,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane
b.
(1S,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane
c.
(1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane
d.
(1S,2S,4S)-1,2-dibromo-4-tert-butylcyclohexane

30.

What is the major organic product obtained from the following reaction?
H2 O
O

H2SO4

OH
OH

OH
1

a.
1
b.
2
c.
3
d.
4
Predict the products of each reaction below.
stereochemistry when relevant.

31.

CH3

H2

a)

Pd

CH3

b)

CH3

Cl2

CCl4

1. O3, CH2Cl2
2. Zn, HOAc

Indicate regiochemistry and

c)

CH3

KMnO4

d)

e)

32.

H3O+
Br
KOH
ethanol

Choose the best reagent from the list below for carrying out each transformation.
Place the letter of the reagent in the blank to the left of the reaction.
a. 1. O3
2. Zn, H3O+

c. 1. OsO4
2. NaHSO3, H2O

b. CH3COOOH

d.

H2O, H2SO4, heat

i)
CH3

O
H

CH3
O
CH3

CH3

ii)

H
CH3
OH

CH3

iii)

34.

a)
b)

For each reaction below suggest structures for alkenes that give the indicated
reaction products. There may be more than one answer in some cases.

H2
Pd
1. H2O, H2SO4
1. BH3, THF
2. H2O2, NaOH, H2O

OH

c)
Br
HBr
ether

d)

ROOR
heat

( CH2CHCH2CHCH2CH )n
C6H5 C6H5 C6H5