13. Alcohols and Carbonyl Compounds

Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.

(b)

An ether extraction of nutmeg gives large quantities of trimyristin, a waxy crystalline solid of melting point 57°C. The IR spectrum of trimyristin shows a very strong absorption at 1733 cm^-1. Basic hydrolysis of trimyristin gives 1 equivalent of glycerol and 3 equivalents of myristic acid (tetradecanoic acid).

(a) Draw the structure of trimyristin.

(b) Predict the products formed when trimyristin is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts.

The esters shown differ only by the alkoxy group.

(i) Predict the product(s) obtained when these react with DIBAl-H.

(ii) Based on your answer, in a sequence like this, would there ever be a need to convert from one ester to another?

(a)

Predict the product of the following reductions.

(a)

Predict the product of the following reductions.

(d)

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

Predict the product of the following reaction sequences.

(a)

Predict the product of the following reductions.

(b)

Predict the product of the following reductions.

(c)

How would you reduce the alkene in the presence of a carboxylic acid?

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

a. 2-methylpropanal

b. cyclohexanone

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

c. 4-tert-butylcyclohexanone

d. acetophenone

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

c. methyl benzoate

d. pentanoic acid

What amides would you react with LiAlH₄ to form the following amines?

a. benzylmethylamine

b. ethylamine

c. diethylamine

d. triethylamine

An unknown alcohol with a molecular formula of C₇H₁₄O was oxidized to an aldehyde with HOCl. When an acidic solution of the alcohol was distilled, two alkenes were obtained. The alkene formed in greater yield was determined to be 1-methylcyclohexene. The other alkene formed the original un-known alcohol when treated with BH₃/THF followed by H₂O₂, HO^-, and H₂O. Identify the unknown alcohol.