1

CH 202
Exam #4
April 11, 2001

Name ______________________________

Page

Points

1

______(12)

2

______(10)

3

______(17)

4

______(21)

5

______(11)

6

______(13)

7

______(16)

Total

______(100)

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

O

O

CH3

O

N
H

Cl

CH3

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

2-Methyl-3-phenylpentanoyl chloride

N,N-dimethyl-2-bromo-benzamide

butanoic anhydride

2

2. Rank the following compounds with regard to acidity. Label the most acidic compound 1 and the least
acidic compound 4. (4 pts)

CH3

CH2

O

CH3

CH2
CH2

CH3

CH3

O

O

CH3

O

CH3

H

H

3. Show the mechanism for an acid catalyzed hydroylisis of the lactone shown below to the gamma
hydroxy acid. (6 pts)

HO

C

O

OH

HO+
3

O

O

+

H2O

3

4. Show a complete arrow pushing mechanism for the following reaction. Show all steps, include all
charges, and draw arrows to show electron flow. (8 pts)

H3CO

C

O

O

O
H

O

CH3O_,then H+to

isolate product

+

CH3OH

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

NH2

O

C

N

OH

O

C

O

CH3

C

N

C

OH

O