Organic Chemistry I Problem Set 20 Answer Key Alkene Reactions Practice Exam

I. _a__ Select the Best Answer 1. a.

CH3 I H I H

HI CH3

b.
CH3 H

c.
CH3 H I

d.
CH2I

e.
No Rxn

_b__

2.

CH3

H2 Pt

CH3

a.
CH 3 H CH 3 H

b.
CH 3 H H CH 3

c.
H CH 3 H CH 3

d.
All of these are formed

_c__

3. a.

2-methyl-2-butene

HBr ROOR

Major Product

b.
CH3 CH3 CH3 CH2 C CH3 Br

c.
CH3 Br CH3 CH CH CH3

d.
CH3 CH3 CH2 C CH2 Br Br

e.
CH3 CH3 CH2 CH CH2 Br

CH3 CH2 C CH2 Br OR

_c__

4. a.

cyclohexene

cold dil KMnO4 OH- / H2O

b.
OH H H

c.
OH H OH H OH

d.
OH H OH OH

e.
O

_d__

5.

propylene

H2SO 4 / H2O reflux

a. b. propylene glycol CH2=C=CH 2 _c__ 6.

c. 1-propanol

d. 2-propanol

e. none of these

1-butene

1. Hg(OAc)2 / H2O / THF 2. NaBH4

Major Product

a. 1,2-butanediol b. 1-butanol c. 2-butanol d. butane

_d__ 7.
cis-2-butene 1. O 3 2. Zn / H+ / H2O

a.

OH OH

b.

OH

c.

d.

CH3 CH CH CH3

CH3 CH2 CH CH3

CH3 C OH

CH3 CH

_a__

8. a.

2-methylpropene

Br2 CCl4

b.
CH3 CH3

c.
CH3 CH3 C CH3 Br

d.
CH3 CH3 C CH2 Br CCl3

e.
CH3 CH3 C CH2 CCl3 Br

CH3 C CH2 Br Br

CH3 CH CH2 Br

_b__

9.
CH3

a. B2H6 b. H2O2 / OH- / H2O

a. cis-2-methylcyclohexane

b. trans-2-methylcyclohexanol

c. 1-methylcyclohexanol

d. 1-methyl-1,2-cyclohexanediol

_c__

10. a. e.

cis-3-hexene
OH OH

KMnO4 / H+ / H2O reflux

b.
O

c.

d.
CH3 CH2 CH2 OH

CH3 CH2 CH CH CH2 CH3 None of these

CH3 CH2 CH

CH3 CH2 C OH

_d__

11. a.
CH3

CH2I2 Zn(Cu)

b.
CH2I

c.

I I

d.

e.

Cl

CH3

_a__

12. a.
CH3CH2

KOH alcohol / heat

CH3 CH2 CH CH CH3

Major product d.
CH3 CH2 C H2C CH CH3 CH3 H

b.
CH3 CH3 H

c.
CH3

CH3

CHCH3 CH3

CH3

CH3

_a__

13. a.
OH Br

E-3-methyl-2-pentene

Br2 / H2O

Major Product

b.
Br OH CH3 CH CH2 C CH3 CH3

c.
Br OH CH3 CH2 C CH CH3 CH3

d.
HO OH CH3 CH2 C CH CH3 CH3

e.
No Rxn

CH3 CH2 C CH CH3 CH3

_e__ a.

14. b.

2,3-dimethyl-2-butene

1. cold, dil KMnO 4 2. HIO4

c.
CH3 OH H3C O CH3 C C CH3 CH3

d.
OH CH3 CH CH3

e.
O CH3 C CH3

f.
O CH3 C C CH3

HO OH CH3 C C CH3 H3C CH3

CH3 CH C CH3 CH3

CH3 CH3

_c__

15.

CH3 CH3 C CH2

KOH CHCl3 / heat

b. acetone and CO 2 c. 1,1-dichloro-2-2-dimethylcyclopropane

a. 1,2-dimethylcyclopropane

d. 1-chloro-2-methyl-2-propanol

OH

_b__

16.

CH3

H2SO 4 heat

a.

b.

c.
OH

d.
CH2

e.
OH

OH

_c__

17.

cis-2-butene

OsO 4 NaHSO3

a.
O CH3 CH

b.
O CH3 C OH HO

c.
OH C H CH3 HO H C H3C

d.
H C CH3 OH H C H3C

_c__

18. a.

propylene

NBS / H2O DMSO

b.
OH Br CH3 CH CH2 OH

c.
OH CH3 CH CH2 Br

d.
OH CH3 CH CH2 OH

e.
CH3 CH2 CH3

CH3 CH CH3

_a__

19.
CH3

HCl

Major Product

a.
CH3 Cl

b.
CH3 H H Cl

c.
CH3 H Cl H

d.
CH2Cl

II.

Answer the following questions: 1. A hydrocarbon of formula C10H14 is treated with ozone, then with acidic zinc in water. The only products are shown below. Write the structure of the hydrocarbon.
CHO O + HC O CH2 CH

CHO

2.

A compound of formula C10H16 is treated with ozone, then with acidic zinc in water. The products of this reaction are shown below. When the original compound is treated with excess H2 / Pt , 1-isopropyl-3-methylcyclohexane is formed. Write the structure of the original compound.
O H2C O CH3 C O CH2 CH2 CH2 CH C O CH3

CH3

CH2 CH3