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PRINT FULL NAME: FIRST______________________LAST (FAMILY

NAME)________________________________

STUDENT #_____________________________________

CHMB42 MIDTERM EXAM- March 8, 2010

TIME ALLOWED- 90 MINUTES

Write answers in spaces provided. There are __ blank pages at the end of the exam
for rough work.

Exams must be written in pen for any remarking claims. (NO PENCIL)

No models, calculators, ‘white out’, pagers or cell phones allowed.

This exam contains __ pages including this page.

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1. Name the following compounds using the IUPAC method: (10 marks)

O
CH3 COCH 2

Cl
Cl

Br

H N

CH2CH 3

O O
CH3 CH 2CH 2COCCH 2CH 2CH3
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2. Of the following pairs of substituents, circle the one which will give a faster rate of
R
bromination. (6)
O
O
OCCH 3
COCH3

if R= a) ,

b) NH2 , NO2

c) CH3 , Cl

For the following substituents on an aromatic ring state their effects- ID, Inductive donation:,
IWD, Inductive withdrawal: DR-donation by resonance:, WR-withdrawal by resonance. Remember
that some of them may have more than one effect. (4)

-CH3 ______________________________, -CN_____________________________

-OH __________________________, Br_________________________________

One ring undergoes electrophilic aromatic substitution more readily than the other. Show with
an’X’ which position gets substituted and explain why in less than 5 words. (3)

O
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Complete the followingPhCOCl,

reactions.
AlCl3 If there are multiple products
Zn(Hg), state which is the MAJOR one. (2
HCl, heat
each)

a)

OCH3
Br2

FeBr 3
NO2
b)

O O
Cl 1. N

CH3 CH3

c)

O NaOH, H 2O, heat

O

d)

6. Provide a detailed stepwise mechanism for the following:

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O
CH 3COCl + HOCH 3
a) (5 marks)
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O
H+
+ H 2O
R NH 2

b) (6 marks)
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