Exam 2

Name:_____________________________
GT Student ID:_____________________________
CHEM 2312 Second Exam 22 February 2010
In taking this examination, you are expected to adhere to the GT academic honor code. At a minimum this requires that
you utilize only the materials supplied to you, and that you do not give help to, or accept help from, others.
(60 points) Multiple choice:
1. What would be the major product of the following reaction
CO 2 H
NO 2
HNO 3
H 2 SO 4 , heat
a.
CO 2 H
NO 2
b.
NO 2
CO 2 H
c.
NO 2 O 2 N
NO 2
CO 2 H
NO 2
O 2 N
d.
CO 2 H
NO 2
2. What would be the major product(s) of the following reaction sequence
OH
1. SOCl 2
O
2. C 6 H 6 , AlCl 3
3. Zn(Hg), HCl, heat
OH
O
O
OH
a. b. c. d.
3. Which reagent(s) would you use to convert toluene to benzyl bromide
a. Br 2 , FeBr 3 b. N-Bromosuccinimide, ROOR, hν c. HBr d. Br 2 /CCl 4 e. NaBr, H 2 SO 4
4. The common name for 4-methylphenol is which of these
a. catechol b. p-cresol c. resorcinol d. p-xylene e. hydroquinone

5. What final product is expected from the following reaction sequence
1. Fe/HCl
NO 2
2. NaHCO 3
Cl
3. Br 2 /H 2 O
4. HONO, 0-5°C
a.
Cl
Br
OH
5. H 3 PO 2
Br
Br
NO 2
b. c. d.
Cl Br Cl
Cl
Br
PO 2 H
Br
HO 2 P
e.
Cl
Br
NO
6. Which of the following might be used to synthesize m-bromoaniline
a.
1. HNO 3 , H 2 SO 4
2. Fe, HCl
3. NaOH, H 2 O
4. Br 2 , H 2 O
b.
1. Br 2 , FeBr 3
2. HNO 3 , H 2 SO 4
3. H 2 , Pt
c.
1. HNO 3 , H 2 SO 4
2. Br 2 , FeBr 3
d.
3. H 2 , Pd-C
1. HNO 3 , H 2 SO 4
2. Fe, HCl
3. NaNO 2 , HCl
4. CuBr
7. Consider the synthesis below. What is compound B
Br
NO 2
A
B
C
NH 2
Br
Br
Br
a.
NO 2 NH 2
NO 2
NH 2
b. c. d.
e.
Br Br
Br
Br
8. Which of the following would be the strongest acid
a.
OH
OH
OH
b. c. d.
H
O
OH
e.
H 3 CO
OH

9. Which product is likely to be obtained during the following reaction of the isotope-labeled allyl ether
( 14 C-isotopic site marked with an asterisk)
O 200°C
*
O OH OH OH OH
a. b. c. d.
e.
*
* * * *
10. Which of the following would be most likely to undergo a nucleophilic substitution reaction with aqueous
sodium hydroxide by an addition-elimination mechanism
a.
Cl
NO 2
Cl H 3 CO Cl
Cl
b. c. d. e.
O 2 N
O 2 N
Cl
OCH 3
NO 2
11. What products(s) would you expect from the following reaction
Cl
NaNH 2
NH 3 (l), –33°C
NH 2 NH 2
CH 3
CH 3 Cl
a.
CH 3
NH 2
CH 3
Cl
CH 3
b. c. d.
H 2 N
e.
CH 3
NH 2
f. products (a) and (b) g. products (d) and (e)
12. Which method could be used for preparing methoxybenzene from phenol
a. NaOH, then CH 3 I b. NaOH, then CH 3 OCH 3 c. NaOH, then NaOCH 3 d. more than one of these

13. (16 points) In the following reaction sequence fill in all missing reagents and intermediates A-D:
A
NBS
Cl
ROOR
B
C
HBr
Cl
ROOR
D
14. (24 points) The following transformations cannot be performed in a single step. Provide a sequence of
reactions to perform each transformation, showing the reagents and structures of all isolated synthetic
intermediates. You may assume that mixtures of isomers can be separated. Note: each synthesis requires
3 or more steps. Do NOT provide mechanisms, just the synthetic steps.
a)
Br

)
OH
Br
CH 3
CH 3