University of Winnipeg

Department of Chemistry

Term Test II

Wednesday March 9, 2016 Duration: 50 minutes

Course: CHEM-2203/3.002 Examiner: A. McCubbin

Student Name:
__________________________________________________________________

Part I (multiple choice): Choose the best answer for each question and indicate it on the
bubblesheet provided.

1. In the reaction shown below, the four possible products of mono-bromination are
shown (A-D). Which of the following best describes the product(s) that would be
observed?

O2N Me Br2
?
FeBr3

A B C D
Br
O2N Me O2 N Me O2N Me O2N Me

Br Br
Br

(a) B is the only major product

(b) C is the only major product
(c) A mixture of A, B and D
(d) A mixture of B and C
(e) A mixture of B and D

2. Which of the following reagents is used to perform benzylic bromination of toluene?

(a) Br2, Cu+2

(b) Br2, FeBr3
(c) Br2, H3O+
(d) NBS, h
(e) All of the above
3. Which of the following statements best describes how the hydroxy group in phenol
affects electrophilic aromatic substitution?

(a) it is ortho/para directing and activates the ring

(b) it is meta directing and activates the ring
(c) it is ortho/para directing and deactivates the ring
(d) it is meta directing and deactivates the ring
(e) it is ortho/para directing and has no effect on the reactivity of the ring

4. Which of the following substrates would be expected to undergo nucleophilic

aromatic substitution via a Meisenheimer complex?

CN Br CN NH2 Me

Br Br Br
(a) (b) (c) (d)

(e) two of the above

5. How many of the following are aromatic?

H
O S

N O
(a) 0
(b) 1
(c) 2
(d) 3
(e) 4

6. How many of the following are anti-aromatic?

O S

(a) 0
(b) 1
(c) 2
(d) 3
(e) 4
7. Which of the following are aromatic?

(a) (b) (c)

S S
S

(d) two of the above (e) all of the above

8. What is the expected product of the following reaction?

O
1. MeMgBr (excess)
OMe ?
+
2. H3O

(a) Me Me (b) Me Me (c) O (d) OMe (e) No reaction

will occur
OH OMe Me Me

9. At which position will the following compound undergo electrophilic aromatic

bromination?

(c) (d)
(b) (e)
H
N

(a)
Br
NO2

10. Which of the following reagents would accomplish the transformation shown?

H OH

(a) H2N-NH2, KOH

(b) NaBH4
(c) LiAlH4
(d) H2/Pd/C
(e) Two of the above would work.
Part II (short answer): Provide an answer to each question below in the space provided.

11. Provide a series of reactions that would accomplish the transformation shown.

OH

O2N
Br
12. Provide a curved arrow mechanism for the following transformation:

OH O O
N Cl Cr O
H
H O (PCC)

CH2Cl2 (dry)