1

CH 201
Exam #4
December 13, 2000

Name ______________________________

Page

Points

1

______(10)

Table of Bond Dissociation Energies

2

______(24)

Bond

DHo(kJ/mole)

3

______(27)

Cl-Cl
Br-Br
I-I
H-Cl
H-Br
H-I
CH3-H
CH3-Cl
CH3-Br
CH3-I
(CH3)3C--H

242
192
150
431
366
297
438
349
293
234
96

4

______(21)

5

______(08)

6

______(10)

Total

______(100)

1. Provide IUPAC names for the following molecules. Don't forget to indicate stereochemistry when
applicable. (4 pts)

H3C

CH2

CH2

CH

CH

O

CH3

CH3

O

CH2

CH3

______________________________

____________________________

2. Provide structures for the following molecules. (6 pts)

benzyl, isopropyl ether

THF

Diphenyl ether

2

3. Predict the products for the following reactions. (12 pts)

Br

CH2CH2OH

SOCl2

Br

OH

H3C

CH2

CH2

OH

acetone

H2CrO4,

PCC

NaH

CH2

OH

CH2Cl2

4. Fill in the appropriate reagents to carry out the following reactions. (12 pts)

H3C

CH

CH2

CH3

OH

H3C

CH

CH2

CH3

O

CH3

OH

O

OH

O

H

1.

2.

O

CH2OH

O

CH2Br

3

5. Predict the products of the following reactions, showing stereochemistry where appropriate. You need
not show the mechanisms for these reactions; simply draw the structures of the products. (27 pts)

CH3
BH3:THF, then H2O2/OH-

a.

OH

1. NaH
2. propyl bromide

b.

H3CH2C
C

C

CH2CH3

H

H

MMPP or MCPBA

c.

OH

H3C

S

O

O

Cl

d.

CH3CH2O-,

e.

CH3CH2OH
CH 3

O

C

O

CH3MgBr, then dilute H3O+

g.

C
O

O

O
C
O

as initiator

C

C

H

H

H

h.

CH3

C

H3C

H

CH2Br

1.
2.

anhydr.ether, Mg

O

,thenH3O+

i.