13. Alcohols and Carbonyl Compounds

Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.

a. heptan-1-ol

Predict the products of the following reactions.

(c) 1-methylcyclohexanol + H₂SO₄, heat

(d) product of (c) + H₂, Pt

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.

(a) butan-1-ol → butanal, CH₃CH₂CH₂CHO

(b) but-2-en-1-ol → but-2-enoic acid, CH₃CH=CH–COOH

(c) butan-2-ol → butan-2-one, CH₃COCH₂CH₃

a. Show the reagents required to form the primary alcohol in each of the following reactions.

a. Show the reagents required to form the primary alcohol in each of the following reactions.

a. Show the reagents required to form the primary alcohol in each of the following reactions.

Show the reagents required to form the primary alcohol in each of the following reactions.

What would have been the product of the preceding reaction with LiAlH₄ if the keto group had not been protected?

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Identify A through O:

What reagent could you use to reduce only the keto group?

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How would you make the following compounds from N-benzylbenzamide?

a. dibenzylamine

What products are obtained from the reaction of the following compounds with LiAlH₄ followed by treatment with dilute acid?

a. ethyl butanoate

b. benzoic acid

Draw the structure of two esters that will be reduced to propanol and butanol by LiAlH₄ (followed by addition of aqueous acid).

Predict the major products of the following reactions.

(f)

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(a)