13. Alcohols and Carbonyl Compounds

Show how you would make each compound, beginning with an alcohol of your choice.

(g)

(h)

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

Predict the product of the following reductions.

(b)

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

When LiAlH₄ reduces 3-methylcyclopentanone, the product mixture contains 60% cis-3-methylcyclopentanol and 40% trans-3-methylcyclopentanol. Use your models, and make three-dimensional drawings to explain this preference for the cis isomer.

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

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

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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.

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

(e)

(f)

Predict the product of the following reductions.

(c)

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

(a)

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

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.

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

a. 2-methylpropanal

b. cyclohexanone