CHEMISTRY 232

QUIZ 2A
NAME:_____________________________ Instructor: A.G. Briggs
REG. NO.:___________________________ Date: October 6, 2010
Marks: 25
Time: 25 minutes
[MARKS]
[4] 1. Identify the indicated sets of protons as homotopic, heterotopic (unrelated), enantiotopic, or
diastereotopic:

a) b)
H H
CH3 H CH2 CH3
C
C C C
CH3
H
H Br H Br
H

[ 4] 2. Give an acceptable name for each of the following structures:

a) b)
Cl CH3 O

CH CH C CH2 CH3CH2 C

[ 4] 3. Draw a structural formula for each of the following compounds: (Ignore chirality, if any.)

a) cis-2-methyl-1,4-hexadiene b) 3-chloropropanal
CHEMISTRY 232 QUIZ 2 A Fall 2010 Page 2

[ 3] 4. The structure of a terpene or terpenoid is shown below. Classify it as a mono-, sesqui-, di, sester-, tri- or
tetraterpene and clearly identify the isoprene units.

Cembrene

[ 2] 5. Define the term isolated diene and give an example. (i.e. Write a condensed structural formula for a
compound that illustrates this.)

[ 8] 6. A graduate student treated 1,3-cyclohexadiene with bromine (Br2, one equivalent) and obtained
two products (ignoring stereoisomers). Her lab partner treated the same starting compound, 1,3-
cyclohexadiene, with HBr (one equivalent) instead, and was surprised to find that only one product was formed
(ignoring stereoisomers). Explain these results. (You need to say what the products are, and you need to write
the intermediate(s) involved, including resonance structures, if any, but a detailed curved arrow mechanism is
not needed.)