Chapter 17: Q48E (page 567)
How would you prepare the following compounds from 1-phenylethanol?
More than one step may be required.
(a) Acetophenone
(b) Benzyl alcohol
(c) m-Bromobenzoic acid
(d) 2-Phenyl-2-propanol
Short Answer
(a)

(b)

(c)

(d)

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Chapter 17: Q48E (page 567)
How would you prepare the following compounds from 1-phenylethanol?
More than one step may be required.
(a) Acetophenone
(b) Benzyl alcohol
(c) m-Bromobenzoic acid
(d) 2-Phenyl-2-propanol
(a)

(b)

(c)

(d)

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Question:For each reaction, write the mechanism using curved arrows for the conversion of the alcohol into the corresponding alkene with POCl3. In each case, explain the regiochemistry of the elimination.
a)

b)

c)

Question:The conversion of 3° alcohols into alkenes under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.
a)

b)

c)

What products would you expect from oxidation of the following compounds with in aqueous acid? With the Dess-Martin periodinane?
Dehydration of trans-2-methylcyclopentanol with POCl3 in pyridine yields predominantly 3-methylcyclopentene. Is the stereochemistry of this dehydration syn or anti? Can you suggest a reason for formation of the observed product? (Make molecular models!)
Benzoquinone is an excellent dienophile in the Diels – Alder reaction. What product would you expect from reaction of benzoquinone with 1 equivalent of 1,3 butadiene? From reaction with 2 equivalents of 1,3 butadiene?
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