CH 202
Exam #4
May 8, 2000

Name ______________________________

Page

Points

1

______(12)

2

______(17)

3

______(26)

4

______(12)

5

______(15)

6

______(18)

Total

______(100)

1. (a)Provide IUPAC names for the following molecules. Don't forget to indicate stereochemistry when
applicable. (6 pts)

H3C

N

CH3

CH2C H3

Cl

HO

CH2CH2NH2

O

NH2

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

N,N-diethyl-N-isopropyl amine

L-Glucose
(open chain form, Fischer Projection)

2-methylaniline

1

3. Label the following sugars as reducing sugars or nonreducing sugars. (9 pts)

HO

CHO

H

CH2OH

H

OH

H

O

OH

OCH3

H

OH

H

H

OH

CH2OH

H

O

O
HO

O

OH
CH
2OH

HO

OH

OH

OH

HOH
2C

4. Rank the following compounds in order of decreasing basicity. Label the mostbasic 1 and the least
basic compound 4. (8 pts)

NH2

NH2

NH2

NH2

CH3

CF3

NO2

2

5. Show the structures of the final products for the following reactions:

(20 pts)

CH2

Br

N-

K+

O

O

CH2
C

O

CH3

H3C
CHCH2
H3C

CH2

Br

NH2

+

1. Mix and heat in EtOH

2. OH-, H2O, Heat

NH3

H2 / Ni

1. NaCN

2. LAH, H2O workup

1. NaNO2/ HCl (HNO2)

2. CuCN

O

(CH3)2NH

NaBH3CN

6. Show an electron pushing mechanism for the hydrolyis of the following glycoside. (6 pts)

O

O

OH

HO

HO

HOH2C

CH3

O

OH
OH

HO

HO

HOH2C

H+
H2O

3