2262-002 Chemistry PROBLEM SET 5
Dr. K. M. Smith March 18, 2008
1) Write full and complete mechanisms for each of the following reactions, showing all electron movements with curved arrows:
A
O
H
HOCH2CH2OH H (B ) O
H O
O
B
1. CN 2. HCl
NC
O
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2) In the boxes below, fill in the product(s), reactants, or reagents, for the following reactions, as appropriate. If you think that no reaction will take place, insert NR in the box.
A) O 1. (CH3)2CuLi 2. CH3CH2OH B) product(s)
product(s) O OH 1. CH3MgBr 2. H3O
C)
product(s) O NHCH3 CH3OH
D)
O OH 1. PBr3/Br2 2. H2O 3. CN
product(s)
E)
product(s) O CH3 excess NaOH excess I2
F) O 1. Br2, H3O 2. CN
product(s)
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G)
O 1. LDA/THF 2. CH3CH2Br
product(s)
H)
starting marterial(s) 1. CN 2. H 3. NaBH4/H2O
OH
CN
I)
starting marterial(s) NH2CH3 CH3NH O
J) O O
reagents
O OCH3 OH
Br
K)
reagents
O CH3 Br Br
L)
O
O O CH3
reagents
O CH2OH
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