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UNIVERSITY OF TORONTO MISSISSAUGA

April 2009 Examination
CHM243H5
P.T. Gunning
3 hours
Aids Allowed: Unboxed Molecular Models, non-programmable
calculators
You may be charged with an academic offence for possessing the following items during
the writing of an exam unless otherwise specified: any unauthorized aids, including but not
limited to calculators, cell phones, pagers, wristwatch calculators, personal digital assistants
(PDAs), iPODS, MP3 players, or any other device. If any of these items are in your
possession in the area of your desk, please turn them off and put them with your
belongings at the front of the room before the examination begins. A penalty MAY BE
imposed if any of these items are kept with you during the writing of your exam.
Please note, students are NOT allowed to petition to RE-WRITE a final examination.
Notes to students:

1. Print your name and student at the top of each page.

2. Marks are indicated in parentheses (# marks) after each
question. Total marks equal 100
3. Answer all questions.
4. Be NEAT.
Question Number

1.
2.
3.
4.
5.
6.
7.
8.
9.
Total Marks

MARK

/10
/10
/15
/15
/10
/10
/10
/10
/10
/100

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1. Show all the steps, with appropriate reagents, for the following transformation.

Br

[10 marks]

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2. Predict the products of the following transformations. Provide the chemical structures
of intermediates A, B, C, D and final product E.

Cl
N

1. NaOH, H2O

SOCl2

2. H3O+

CH2Cl2, NEt3

MgBr

1.

AlCl3
19 hours, rt

2. H3O+ (work up)

H2SO4, 75 oC

[10 Marks]

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3. Suggest a synthetic route to molecule B from the starting material A. Multiple steps
are required to complete this synthesis. Be sure to include all reagents, solvents and
conditions required for each transformation.

multiple steps required

[15 Marks]

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4. Give a detailed mechanism for the following reaction. Show each of the products of
the reaction.
O
N

HCl, H2O
r.t., 2hrs

?
[15 Marks]

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5. Propose a mechanism for the following transformation. No alcohol is used in the

formation of the new acetal group, only catalytic HCl.

catalytic HCl
H

H2O

O
H

[10 Marks]

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6. Show all the steps, with appropriate reagents, for the following transformation.
O

[10 Marks]

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7. Provide the product for each numerical step in each of the following reactions
sequences.
1) SOCl2, CH2Cl2
2) liq. NH3

O
OH

3) SOCl2, benzene, 60 oC
4) (i) CH3MgBr, ether
(ii) H3O+

5) (i) NaBH4, EtOH

(ii) H3O+

[10 Marks]

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8. (a) Provide the product for each numerical step in each of the following reactions
sequences.
1) CrO3, H3O+
OH

2) (i) CH3NH2 (1 equiv)

(ii) H3O+, workup
3) H2NNH2, NaOH

(b) Provide a full mechanism for the synthetic transformation in part 3.

[10 Marks]

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9. Show all the steps, with appropriate reagents, for the following transformation.
OH

H 2N

NH2

[10 Marks]

End of exam

Total marks = 100

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No Question: extra sheet

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