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CHM 2211: ORGANIC CHEMISTRY II
Exam 2 – March 1, 2007
Section 02, Professor A. Herriott
Instructions: No electronic devices (calculators, cell phones, laptops, etc) may be used or
consulted during the exam. All scrap work should be done on the extra page provided; no
additional paper may be used. Sign your name to confirm your acceptance of these policies.
“I have neither given nor received assistance on this exam” ____________________________
Panther ID ____________________
Section B: ( 28 points, 4 each) Circle the letter of the correct answer.
1.
Which one of the following structures in each group is aromatic?
a)
b)
c)
d)
e)
2.
H
a)
b)
CH2
N CH3
c)
O
H
CH2
H
d)
e)
H
H
3. Which of the following compounds is the strongest acid?
. a) benzoic acid; b) 2,4-dinitrobenzoic acid; c) p-toluic acid; d) phenol; e) phenylacetic acid
4. Which of the following compounds is the strongest acid?
O
OH
CO2H
a)
CO2H
b)
c)
Cl2CHCO2H
d)
e)
5. Which of the following reagents is not a reducing agent:
a) NaBH4
b) Zn (Hg),HCl
c) H2, Pd
d) K2Cr2O7, dil H2SO4
e) LiAlH(OC(CH3)3
6. In the reduction of 2-butanone to (2)-butanol using the (S)-CBS reagent (2-methyloxazaborolidine + BH3), what is transferred in the critical step in the reaction mechanism?
a) a hydride ion, H- b) a hydrogen radical, H
c) a proton, H+ d) both hydrogens
simultaneously as molecular hydrogen, H2 e) a hydroxy group, OH
7. The amino acid glycine is soluble in water. At pH 1, it will exist largely in which form?
H2
C
a)
NH2
H2
C
H2
C
CO2H
b
NH3
CO2
c)
NH3
CO2H
d)
O
H2
C
NH2
CO2
e)
HN
O
Org II exam, p.2
Section A (48 points, 4 each – answer 12 of the 13 questions, marking clearly the one you
choose to omit; if none is marked, the last answer will be omitted) Give the major organic
product(s) of the following reactions, including stereochemistry if appropriate.
OCH3
HNO3
1.
H2SO4
2.
1. (CH3CH2)2CuLi
O
C
2. H2O
Cl
NO2
KMnO4
3.
1. LiAlH4
4.
2. H20
O
5.
NaOH
CO2H
O
6.
H2
C
C
H3C
O
+
CH3
CH3CH2CH2CH2MgBr
2 equivalents
2. H2O
Org II exam, p.3
CH3
O
AlCl3
7.
Cl
H3C
Br
8.
1. Mg, ether
2. CH3CH2 CHO
3. Water
Br2
9.
hv
NO2
S03
H2SO4
10.
H3C
O
11.
1. (CH3)2CHLi
CH2
H
2. H2O
OH
12.
CrO3
AlCl3
13.
Cl
Org II exam, p.4
C. ( 12 points, 6 each) Indicate the reagents for the following two-step conversions:
Cl
1.
NO2
OH
2.
OH
D. (12 points, 6 each) With your available starting materials being benzene and any organic
compounds of 4 carbons or less, and any needed inorganic reagents, provide a reasonable
synthetic path to the following compounds, showing all reagents.
1.
Org II exam, p.5
2.
Bonus: (2 points): When two equivalents of N,N-dimethylaniline are reacted with benzaldehyde
in HCl, an addition product is formed in 75% yield, which is very easily oxidized to a cationic
dye called Malachite Green. Identify the addition product and explain why it is easily oxidized
to a dye.