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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