13. Alcohols and Carbonyl Compounds

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.

(e)

What is the product of the reacion?

What is the product of the reaction?

Show a mechanism for the lithium aluminum hydride reduction of benzoic anhydride.

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.

(e)

Propose a mechanism for the following reaction:

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

a. dibenzylamine

Show how this 1° alcohol can be made from the following:

(c) a 7-carbon aldehyde

(d) a carboxylic acid

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(j)

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.

(d)

Suggest the most appropriate reagent for each synthesis, and explain your choice.

(c)

What alcohols are obtained from the reduction of the following compounds with sodium borohydride?

c. 4-tert-butylcyclohexanone

d. acetophenone

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

(d) Ph₂CHOH

(e) PhCH₂OH

(f) PhCOOH

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

(d)