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Alcohols/Synthesis
Name: _______________________
1. How would you synthesize the following from an appropriate alkene using appropriate
reagents?
a) .
b) .
c) .
d) .
e) .
f) .
Dr. Gupta/Alcohols/Synthesis-Wade/Page 1 of 5
2. Show how you would accomplish the following transformations.
a) .
b) .
c) .
d) .
e) .
f) .
Dr. Gupta/Alcohols/Synthesis-Wade/Page 2 of 5
3. Draw the organic products you would expect to isolate from the following reactions after
hydrolysis.
a) .
b) .
c) .
d) .Ph-CHO +
e) .
f) Ph-MgBr + PhCOPh
g)
h) .
i) .
j) .
Dr. Gupta/Alcohols/Synthesis-Wade/Page 3 of 5
k) .
l) .
m) .
n) .
4. Show how you would synthesize:
a) 2-phenylethanol by addition of formaldehyde to a suitable Grignard reagent
b) 2-phenylethanol from a suitable alkene
c) Cyclohexylmethanol from an alkyl halide using SN2 reaction
d) 2,5-dimethylhexane from a four carbon alkyl halide.
Dr. Gupta/Alcohols/Synthesis-Wade/Page 4 of 5
5. What carbonyl compound and reducing agent would you use to carry out the reduction to
form the following alcohols?
a) n-octanol
b) 1-cyclohexyl-1-propanol
c) 1-phenyl-1-butanol
d) .
e) .
f) .
Dr. Gupta/Alcohols/Synthesis-Wade/Page 5 of 5