name ______________________________

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1-10. Multiple Choice. Provide the best answer for each question. There is only one answer for each
question. (3 pts each, 30 pts total)

1. Which of the following is NOT a resonance structure for benzene?

a) b) c) d)

2. Which of the following would you expect to be the major product from the nitration of
4-bromobiphenyl?

Br HNO3, H2SO 4

b)
a) O2N
Br NO2
Br

c) NO2 d)
There will be NO reaction
Br

3. Which of the following would NOT be a product from the Friedel-Crafts alkylation of benzene with
1-bromopropane?

a) b)

c) d)
a, b and c are all possible products
for the reaction

4. Which of the following does NOT contain a conjugated system.

a) b) O c) d)
CH3
H3C N
CH3

5. Which of the following reagents will react with (R)-2-octanol to give an optically active product.

a) b) c) d) a, b, and c will all give an

PBr3 SOCl2 TosCl optically active product
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6. The pKa of phenol is 10. Which of the following compounds would you expect to be LESS acidic
than phenol?

a) OH b) OH c) OH d) SH

NO2
C NH2
N
7. Which of the following compounds is aromatic?

a) b) + c) d)
N None. i.e., a, b and c are
not aromatic compounds
O

8. Which of the following compounds is anti-aromatic?

a) b) + c) d) _

9. Which of the following oxidants can be used to convert 1-hexanol to hexanal?

[O] O
OH
H
1-hexanol hexanal

a) b) c) d)
CrO3, H3O+ a, b, and c will all give the
PCC KMnO4 hexanal as the major product

10. Which of the following compounds is predicted to undergo electrophilic aromatic nitration the
slowest?

a) N b) OCH3 c) d) Compounds a, b, and c would

C undergo nitration at
approximately the same rate
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11. Anthracene is shown below. There are a total of four resonance structures for anthracene. Draw the
remaining three resonances structures and draw curved arrows showing how the resonances
structures can be interconverted. (12 pts)

12. Answer the following questions concerning the cycloheptatrienyl cation (also known as the
tropylium ion), shown below. (12 pts)

+
a) How many conjugated p-orbitals does the tropylium ion have? 2 pts
7

b) According to Hckel, is the tropylium ion aromatic? Explain briefly although precisely Hckel
criteria for aromaticity? 4 pts

Yes: According to Hckel, aromatic systems have 4n+2 -electrons, where n is an

integer. The tropylium ion has 6--electrons which follows Hckel's criteria

c) Draw a molecular orbital diagram of the tropylium ion showing the relative energies of the MO's
and where the electrons are. You do not need to draw the phases of the individual orbitals. 8 pts

NB
+
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13. From the list below, provide the proper reagents, needed to complete the following reactions. (3 pts
each, 18 pts total)

A. Br2, FeBr 3 I. NaOH, 300 C

B. HNO3, H 2SO4 J. 1. LiAlH4 2. H3O+
C. SO3, H 2SO4 K . 1. NaBH4 2. H3O+
D. I2, CuCl 2 L. 1 Hg(OAc)2, H 2O 2. NaBH 4
E. Cl2, FeCl 3 M. 1. B 2H6 2. H2O2, NaOH, H2O
F. KMnO4 N . PBr3
G. NBS, peroxides, O. CrO3, H 3O+
H. H2, Pd/C P . PCC

O
J
OH
OCH3

O
H

A
Br

Br
G

SO3H OH
I
H3C H3C

O O OH O
K
OCH3 OCH3
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14. Give the major product for the following reactions (9 pts).

OCH3 O O OCH3
H3C Cl

AlCl3
Cl Cl

O 1) H3C-MgBr
(excess) HO
OCH3
2) H3O+

(H3C)3SiCl,
O O
(CH3CH 2)3N
(CH 3)3Si
HO H O H

15. Starting from benzene, any alkyl halide, any acid chloride and any necessary reagents, synthesize
4-chloro-2-nitroaniline. (10 pts)

H2, Pd/C
NO2 NH2
-or-
HNO3, H2SO4 SnCl2

NH2 NH2
Cl2, FeCl3 HNO3, H2SO4 NO2

Cl Cl
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16. Provide a structure consistent with the following spectroscopic data.

Formula: C8H9OCl 4 degrees of unsaturation

IR: broad absorption from 3600-3400 cm-1 -OH group present
13C NMR: 138, 131, 129, 127, 65, 39 138, 131, 129, 127:
4 aromatic 13C peaks=
p-disubstituted benzene

1H NMR: 7.50 d, J= 9.0, 2H p-disusbtituted benzene

7.10 d, J= 9.0, 2H

3.70 t, J= 5.0, 2H -CH 2 -CH 2 - in the O-C-H

region
3.00 s, 1H perhaps an O-H

2.70 t, J= 5.0, 2H -CH 2 -CH 2 - in the Ar-CH

region

Data is consistent with the following two structures:

OH Cl

Cl HO

____________________________________________________________________________________

Problem 1-10:________ (30 pts) 14:________ (9 pts)

11:________ (12 pts) 15:________ (10 pts)

12:________ (12 pts) 16:________ (9 pts)

13:________ (18 pts)

Total out of 100: _________