CH 201
Exam #3
November 17, 2000

Name ______________________________

Page

Points

1

______(14)

2

______(12)

3

______(24)

4

______(14)

5

______(12)

6

______(18)

7

______(06)

Total

______(100)

1. a. Provide IUPAC names for the following molecules (don’t forget stereochemistry). (6 pts)

H3C

CH2

CH2

H3C

CH2CH3

CH2CH3

CH2

CH2

CH2

CH2

CH3

CH2Br

H3C

H3C

________________________

___________________________

b. Provide structures for the following molecules. (4 pts)
(Z)-3-isopropyl-2-hexene(Z)-2,3-dichloro-2-butene

2. Calculate the unsaturation number for each of the following compounds. (4 pts)
a. C10H16Cl2b. C10H18N2

1

3. Circle the stronger acid. (3 pts)

HI or HBr

BrCH2COOHorClCH2COOH

Phenoloracetic acid

4. Write an arrow pushing mechanism for the following reaction. (5 pts)

CH3

CH

CH3

CH3

CH3

85% H3PO4

OH

Heat

5. In each group of compounds below, circle the compound expected to have the lowestheat of
hydrogentation. (4 pts)

vs.

vs.

vs.

2

6. Predict the products of the following reactions showing the proper stereochemistryand
regiochemistry. (24 pts)

H3C

C

C

CH2

CH3

CH3

CH2CH3

HCl

H3C

H3C

Pd/CaCO3
( Lindlar c atalyst)

H2

Br2

H3C

C

C

CH2

CH3

Br2/H2O

1 eq. H2

Pd/C

1. Na/NH3

2.NH4Cl

C

C

CH3

H3C

H

H

HC

CH

H3C

CH3

CH2N2

heat

H3C

CH3

2. HO, OH-
2

1. Cold KMnO4

3