CHM 138H INTRODUCTORY ORGANIC CHEMISTRY I TERM TEST II March 18th 2010 TOTAL MARKS: 70

NAME (PRINT): ___________________________ TUTORIAL GROUP #: ___________

Student #: ______________________

Answer all questions in the spaces provided on the accompanying answer sheet. It is attached to the back of the test paper. You may detach the answer sheet. Nothing on this question sheet will be marked. PRINT YOUR NAME, STUDENT NUMBER, and TUTORIAL GROUP NUMBER on this test paper and on the answer sheet. Write all answers in blue or black ink. You may use unboxed molecular models. Calculators are not permitted. A periodic table is included on page 6 of the test. At the end of the test, place the answer sheet inside the test paper and HAND BOTH IN.

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Part I (20 marks) Multiple Choice (2 marks each). Use the structure below to answer questions 1-7.

1.

How many degrees of unsaturation are found in the above compound? a) 2 b) 3 c) 4 d) 5 e) 6

2.

What term best describes the alkene in the above compound? a) R b) S c) Z d) E e) trans

3.

What is the configuration of the chirality centres (stereocentres) labelled 1 and 2 in the above compound? a) 1 is R and 2 is S b) 1 is R and 2 is R c) 1 is S and 2 is S d) 1 is S and 2 is R e) The centres are pro-S to one another

4.

How many prochiral sp3 centres are present in the above compound? a) 7 b) 8 c) 9 d) 10 e) 11

5.

What are the hybridizations of the oxygen atoms labelled 3 and 4 in the above compound? a) 3 is sp3 and 4 is sp3 b) 3 is sp2 and 4 is sp3 c) 3 is sp3 and 4 is sp2 d) 3 is sp2 and 4 is sp2

6.

If the compound above was halogenated with Cl2 which of the following statements would be true? a) Four stereoisomers would result and they would be diastereomers b) Two stereoisomers would result and they would be enantiomers c) Two stereoisomers would result and they would be meso compounds d) Four stereoisomers would result and there would be two enantiomers and two diastereomers e) Two stereoisomers would result and they would be diastereomers Page 2 of 6

7.

If the compound above was hydrated with mercury acetate (Hg(OAc)2) followed by treatment with sodium borohydride (NaBH4), which of the following statements would be true? a) a tertiary alcohol would result b) two compounds with the same boiling point would result c) a mixture of enantiomers would result d) A and C e) A and B

8. a)

Which of the following structures represents (Z)-2,3-dibromo-4-methylpentene?

Br

b)

Br

c)
Br

Br

Br

Br

d)

Br

Br

e)

Br

Br

9.

The following forward reaction is

O H 3CO OCH 3

H+ + H2O K=1000 T=273 K

+ 2 CH3OH

a) b) c) d) e)

exergonic and entropically favoured exergonic and entropically disfavoured exergonic and a rearrangement reaction endergonic and entropically favoured endergonic and entropically disfavoured

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10.

Rank the carbocations shown below in order of decreasing stability (most stable to least stable).
CH3 O

CH3
H H CH3

CH3

H CF3

II

III

IV

a) b) c) d) e)

II > IV > III > I III > I > IV > II IV > II > I > III II > IV > I > III III > II > I > IV END OF MULTIPLE CHOICE QUESTIONS

Part II Short Answer Questions 1. (10 marks) Using curved arrows to show the movement of electrons, draw a mechanism to explain the following transformation. Be sure to include the structures of all relevant intermediates but do not draw the structures of transition states. NOTE: you are not required to show the stereochemistry of the reactants, intermediates or products.
Cl

OH

Cl2

HCl

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2. (13 marks) The free energy diagram template on your answer sheet is for the reaction below.

On the free energy diagram clearly add the following features: a) b) c) d) e) f) A label (R) for the reactant A label (P) for the product TS to indicate each reaction transition state The positions and structures of any reaction intermediates A label (G(for)) to show the activation energy of the forward reaction A label (G(rev)) to show the activation energy of the reverse reaction

3. (27 marks) Fill in the boxes on the answer sheet with the appropriate reactants (A, F, H), reagents (B, G, I) or major organic products (C, D, E) for the following reactions. Be sure to include stereochemistry where important.

i).

A
an alkene

Cl

Cl

ii).

H2, Pd/C

iii).
1. a) BH3; b) NaOH,H2O2 2. HIO4 OH

D and E

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iv).
OH

F
an alkene

OH

v).
Br

H
an alkene

- END OF THE TEST -

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