1

CH 202
Exam #4
April 12, 2000

Name ______________________________

Page

Points

1

______(12)

2

______(14)

3

______(17)

4

______(21)

5

______(11)

6

______(12)

7

______(13)

Total

______(100)

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

O

O

O2N

O

N

H3C

CH3

O

Cl

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

N-methylbenzamide

butylpentanoate

propionic anhydride

2

2. Rank the following compounds with regard to expected reactivity toward nucleophilic acyl substitution.
Label the most reactive compound 1 and the least reactive compound 4. (4 pts)

CH3

O

O

O

CH3

CH3

O

N

CH3

CH3

CH3

O

O

CH3

CH3

O

Cl

3. Circle the most acidic proton(s) in eachof the following molecules (4 pts)

CH2

OH

O

H3C

CH2

O

CH3

O

a.

b.

4. Show the mechanism for an acid catalyzed hydroylisis of an ester to an acid. (6 pts)

OCH3

O

OH

O

+

H2O

+CH3OH

H+

3

5. Show a complete arrow pushing mechanism for the following reaction. (8 pts)

O

O

O

O

1. NaOMe

2. HCl/H2O

O

O

O

6. Fill in the reagents for the following reactions. (9 pts)

NH2

O

C

N

C

N

OH

O

OH

O

O

O

CH3