Chemistry 52
ANSWER KEY
REVIEW QUESTIONS
Chapter 20
1. Identify each of the isomers below as cis- or trans- and name using the IUPAC system:
a)
trans-2-butene
b)
cis-2-pentene
c)
trans-3-heptene
2. Name each aromatic compound shown below as a toluene derivative:
a)
H O CH 3 c)
CH 3 Cl Br 3-hydroxytoluene or
m-hydroxytoluene
b)
4-bromo-3-chlorotoluene or
p-bromo-m-chlorotoluene
d)
CH 3 CH 3 Cl H 3C 2-chlorotoluene or
o-chlorotoluene
4-ethyltoluene or
p-ethyltoluene
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3. For each compound shown below, determine if a cis/trans isomer is possible or not.
a)
CH3CH=CHCH3
Yes
b)
CH2=CHCH2CH3
No
(2 H’s on C no. 1)
No
(2 CH3’s on C no. 1)
H 3 C CH 3 c)
CH 3 CH 3 d)
Yes
H 3 C H 3 C 4. Write condensed structural formula for each compound below:
a) 2,3-dichloro-1-butene
b) trans-3-hexene
CH 3 CH 3 c) 1,2,4-trimethylbenzene
CH 3 d) p-ethyltoluene
H 3C 2
CH 3 5. Complete each of the reactions shown below. If reactions produce more than
one isomer, draw structure and name each isomer.
a)
+ H
CH3CH2CH=CH2 + H2O ¾¾
® 2­butanol H 3 C b)
H 3 C CH 3 H 3 C ¾¾
® + HI
I CH 3 H 3 C 2­iodo­2­methylbutane OH c) H 3 C H + heat
¾¾¾
®
H 3 C CH 3 CH 3 cis and trans-2-pentene
d)
Pt ¾¾
¾
®
heat
+ H2 2-methylpropane
Br e)
H 2 C CH 3 Br
+ Br2 ¾¾
®
H 3 C CH 3 H 3 C 1,2-dibromo-3-methylbutane
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