13. Alcohols and Carbonyl Compounds

Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.

(a) N-ethylbenzamide → benzylethylamine

(b) ethyl benzoate → N-ethylbenzamide

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(d)

What is the product of the reaction?

What is the product of the reacion?

What is the product of the reaction?

Predict the products you would expect from the reaction of LiALH₄ followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(c) Ph-COOH

Predict the products you would expect from the reaction of LiAlH₄ followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(a) CH₃–(CH₂)₈–CHO

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(c) Ph-COOH

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(a) CH₃–(CH₂)₈–CHO

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(b) 1-cyclohexylpropan-1-ol

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(a) octan-1-ol

Show how you would accomplish the following transformations. You may use any additional reagents you need.

(c)

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

c. 2-methylhexan-3-ol

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

a. heptan-1-ol