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Thursday February 20, 2014
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You have 60 minutes to complete the exam.
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Chem 2536 Exam 1
Thursday February 20, 2014
Multiple Choice Section (Questions are with 5 points each)
1. Which structure below is m-bromobenzoic acid?
0
e Br OH OH
‘OH oo Tr Sy none of these
Bi
Br "
@)
A Cc D £
2. Which of the following absorbs UV light at the longest wavelength?
a on~conm
A 8B coc @) ¢
3. Which compound is the Lewis acid in the following mechanistic step?
°
§
QO we — Gy
x out
O=N=z0 Cr oO none ofthese —_ alll of these
A c D E
4. Choose the correct reagents for the transformation below.
O-— oe
Bro NBS, Bro, NaBr none of these
ROOR, FeBr3
heat
A B GD D E
Chem 2536 Exam 1
Thursday February 20, 2014
11. What is (are) the product(s) of the reaction below?
|
N@ ¢ carbocadion
CQ ct Cea CON ernest
AICly
| | \ |
N6é NSé “NS “N@
Cue OY O, none of these
A
B j D E
12. From the answers below, select the correct starting material for the reaction shown:
-———— OH
NaOH NO, Aadkeogh lie
COCONNGAT]E
sebst iy hon
S03H
NH F OH
NO2 NO2 NO,
none of these
SO3H S03H SO3H SO3H
A B c D E
Chem 2536 Exam 1
Thursday February 20, 2014
Short Answer Section (Questions are with 10 points each)
13. Answer the following questions on electrophilic aromatic substitution.
a. Draw the structure of phenol.
b. Draw the para-substituted product of the reaction of phenol with H2SO, and HNO3.
c. Draw the cationic intermediate for the reaction above, Show all four resonance structures for
this intermediate and include curved arrows to show transformations between these structures.
oH or
a » Oo
No
on on @,—-H oH
€ N q
H
of © on Wt Nox H Woy H
14. Propose a synthesis of m-bromonitrobenzene from benzene. Include all necessary reagents.
‘You do not need to draw a mechanism.
NOg
No
a
Ha So4 Ba
ts a)
OO HME, Fe Br. 3
Be
Chem 2536 Exam 1
Thursday February 20, 2014
15. Fill in the curved arrows for the sulfonation of toluene (B: represents any base in the reaction
mixture).
2 ® 08,0
HO-SO3;H_ = + =~ H-OSO3H H,0-SO3H sg
re “Ww a) on
+
“OSO3H
5
® S0H p: Se SO3H
BH +
16, Fill in the missing reagents and structures for the synthesis of 4-phenylazophenol.
4, [AlatlOg Hel
yy te
2. Pd/C
2. oH
O
Bonus. Propose a mechanism for the following synthesis:
HsSO4 Ark
‘OH
x
x H2 080,14
A at 7 —s
