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Organic Chemistry I
Spring 2013
Practice test
1. Name the following compounds:
a. 5-tert-butyl-7-isopropyl-6-sec-butyl-undecane
b. cis-2-(5,6-dimethylheptyl)-6-(3-methylpentyl)piperidine
c. trans -2-nonyl-3-octyl-tetrahydrofuran
d. trans-1,6-dimethylbicyclo[4.3.0]nonane
e. cis-6,8-ditert-butylspiro[3.5]nonane
f. 1,6-dimethylcyclohexene
g. (Z)-3-bromo-4-fluoro-5-methyl-oct-4-ene
h. (E)-8-(1-chloroethyl)nonadec-8-ene
2. Draw the structures of the following compounds:

a

b

e

c

f

d

g

h

3. Draw the structure of the following compounds in Newman projections and in chair conformations:

a

b

c

d

e

4. Draw the most stable isomer of 1-tert-butyl-3-methylcyclohexane.

a. Which atoms/groups are
i. gauche to axial hydrogen on C2
A: t-butyl, C6, methyl, C4
ii. anti to equatorial substituent on C3
A: C5, C1
b. What is the relationship between:
i. tert-butyl group and equatorial hydrogen on C2
A: gauche
ii. equatorial hydrogen on C4 and C6
A: anti
5. Draw all isomers of 4-tert-butyl-2-ethyl-1-methylcyclohexane (ignore mirror images) in their most stable conformations. Arrange the structures from the least stable to the most stable.

6. Cyclohexylmethanol and 1-methylcyclohexanol are converted to their corresponding bromides. Write a suitable mechanism for each reaction, and assign each the appropriate symbol (SN1 or SN2). OH

O
H

H Br

H
+

:Br :

SN2

:Br :
O
H

H

Br

+

H2O

OH

O

H Br

O

+

H2O

+

:Br :

SN1

:Br :
Br

7. Give the structure of the principal organic product formed by photochemical bromination of methylcyclopropane, draw the mechanism of the reaction.
Br2, h
h
Br Br

H

.

.Br
Br Br

Br

2Br .

.

+

HBr

Br

+ .Br

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