NAME __________________________

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 NAME __________________________

THIRD HOUR EXAMINATION

CHEMISTRY 241-001
December 4, 2013

Please put your name on all 10 pages of the examination.

Be certain that you have all 4 questions.

Question Score

II

III

IV

Total

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 NAME __________________________

I. (30 points) Provide the missing reagents or products for the following reactions. Pay particular
attention to stereochemistry where applicable.

A.
?
O
H

B.

1. O3
?
2. MeSMe

C.
MgBr O H 3O+
2 equiv +
O ?

D.
OH
O
?
? catalytic
H 2SO 4 HO H

E.
OH CN
?

optically pure optically pure

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 NAME __________________________

F.
O D D
?
OCH3 OH

G.
xs. LiAlH 4
?
O

O HIO 4
OH ?
OH
xs.NaBH4
?

H.
OH D
?

I.

Cl OH
? HBr

CH2Cl2
?

J.

xs. Na 2Cr2O7 OH xs PCC

? H 2SO 4
?
HO

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 NAME __________________________

II. (36 points) Using the arrow formalism, draw detailed, stepwise mechanisms for the reactions below.
Show each intermediate (not transition states) along the reaction pathway.

A. (6 points)
Br + 2 Li Li + LiBr

B. (8 points)

HO O
O OH H 2SO 4

OCH3
OCH3 OCH3 OCH3

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 NAME __________________________

C. (12 points)

B
1. H
H CHO
2. aqueous NaOH, H 2O2

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D. (10 points)
catalytic

O N N O
OH + + Et 3NHCl
Cl O
Et 3N
CH2Cl2

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III. (29 points) Using the starting materials given and any other substrates or reagents, outline
syntheses of the desired products.

A. (11 points) (Two starting materials are the source of all carbons)
OCH2CH2CH 3
O ? O
+ O
Cl

B. (7 points)
? OH

(source of all carbons)

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 NAME __________________________

C. (11 points)

? O
H H
H 3CO

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 NAME __________________________

IV. (5 points) Rank order the following compounds (1 5; 1 = most reactive) according to their reactivity
with nucleophiles

O O O O O
N(CH 3)2 H OCH3 Cl

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