1
CHEM 10052
Summer 1999
Final Exam
Name____________________
ss#______________________
1) Identify the functional groups in the following compound (8 pts.).
O
O
CH3
alkene
NH
amide
ketone
O
ether
2) Give examples of compounds that contain the following functional groups (8 pts.).
a) alcohol
b) acetal
CH3O OCH3
CH3OH
c) carboxylic acid
CH3
O
C
OH
d) thiol
CH3SH
3) Name the following compounds using either common or systematic nomenclature (8 pts).
CH3CH2
H
C C
H
CH3
a)
trans-2-pentene
OH
OH
O
CH3CH2 CH CH
OH
NO2
b)
3-hydroxy-2-nitropentanoic acid
OCH2CH3
OCH3
c)
phenol
d)
1-ethoxy-1-methoxycyclobutane
2
4) Draw structural formulas for the following compounds (8 pts).
a) trans-2-methylcyclopentanol
b) m-nitrobenzoic acid
O
OH
O2N
CH3
c) 3-hydroxy-2-mercaptohexanal
OH
d) 2-phenylhexanal
O
H3 C
OH O
H3C
H
H
SH
5) Compare the molecular structure and physical properties of carboxylic acids and ethers. Include
descriptions of geometry, orbital hybridization, hydrogen bonding, relative boiling points, and
water solubility. (8 pts).
See Notes
6) Using an orbital diagram describe the bonding in a double bond. Label the  and  bonds,
indicate bond angles, and describe the molecular geometry and orbital hybridization. (6 pts.)
See Notes
7) Draw and name two isomers with the chemical formula C6H12O2. (6 pts.)
O
O
H3C
H3C
OH
OH
CH3
hexanoic acid
2-methylpentanoic acid
8) Predict the major products for the following reactions. (2 pts. each)
O
a) Ph
O
Ph + CH3CH2NH2
O
CH3
c) CH3CH2CH2
d) CH3CH2
O
C
O
C
OH
NHCH2CH3
+
Ph
O
C
OH
CH3
OH
H2O
H2SO4
b)
Ph
O
C
[R]
CH3CH2CH2
OH + CH3CH2NH2
O
C
H

CH3CH2
[R]
O
C
CH3CH2CH2
OH
CH2
NHCH2CH3 + H2O
3
NH2
NHCH2CH3
1) CH3CH2Br
2) NaOH
e)
O
C
CH3CH2
OH O
cat. NaOH
H
CH3CH2
H
CH3
f)
CH3O
O
OCH3
H2O, H+
+ 2CH3OH
g)
O
O
OH
OCH3
H2SO4
+ CH3OH
h)
CH3CH2CH2
O
O
C
CH C

O
CH3
i)
OH
j)
OH
CH3
H2SO4

CH CH2CH3
H3C
CH3
H
C C
H
H3C
CH3
+ H2O
9) Provide the proper reagents required for the following transformations (2 pts. ea.)
O
N
N
H
a)
HNO3
H2SO4
b)
NO2
O
[O]
CH3CH 2CH2OH
c)
C
CH3CH 2
H
10) Write a detailed mechanism for the hydration of propene. (6 pts.)
See Notes
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11) Write a detailed mechanism for hydrolysis of esters. (6 pts.)
See Notes
12) Circle the five chiral molecules. (8pts.)
CHO
H
CHO
OH
O2N
OH
H
CH3
OH
HO
CHO
H
CH2OH
H
CH3
H
meso
CH2OH
Br
Br
OH
NO 2
H
OH
H
OH
CH2OH
Br
meso
meso
CH2OH
O
O
CH3
O
H
HO
OH
H
CH2OH
Bonus: Identify the three meso compounds above. (9 pts).