Chapter 17: Q 32 E (page 567)
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)

Short Answer
a)

b)

c)

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Chapter 17: Q 32 E (page 567)
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)

a)

b)

c)

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How would you prepare the following substances from cyclopentanol?
More than one step may be required.
(a) Cyclopentanone
(b) Cyclopentene
(c) 1-Methylcyclopentanol
(d) trans-2-Methylcyclopentanol
p-Nitrophenol and 2,6-dimethyl-4-nitrophenol both have pKa 5 7.15, but 3,5-dimethyl-4-nitrophenol has pKa 5 8.25. Why is 3,5-dimethyl-4- nitrophenol so much less acidic?

The following data for isomeric four-carbon alcohols show that there is a decrease in boiling point with increasing substitution of the OH-bearing carbon. How might you account for this trend?
1-Butanol, bp
2-Butanol, bp
2-Methyl-2-propanol, bp
Question: What carbonyl compounds give the following alcohols on reduction with ? Show all possibilities.
(a)

(b)

(c)

(d)
Draw the structure of the carbonyl compound(s) from which each of the following alcohols might have been prepared, and show the products you would obtain by treatment of each alcohol with (1) Na metal, (2) , and (3) Dess-Martin periodinane.
(a)

(b)

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