13. Alcohols and Carbonyl Compounds

(a) Based on Figure 24.23, explain why meta-dihydroxybenzene is not oxidized to meta-quinone.

(b) If a meta-quinone is not produced, what would you expect the product of the oxidation of meta-dihydroxybenzene to be?

Predict the product of the oxidation reactions shown.

(b)

If there is no water present, the hydrate of an aldehyde cannot form. Could an aldehyde itself (not the hydrate) be oxidized to a carboxylic acid? Why?

In Hinkley, the cleanup continues today. In one process PG&E is using to mitigate the chromium(VI) toxicity, ethanol is injected into the soil. How would this reduce the chromium(VI) contamination?

Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.

(b)

Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.

(c)

Oxidation of the phenol shown gives a single quinone product. Predict this product and explain why it is the only one formed.

Predict the product of the following oxidation reactions.

(c)

Phenol oxidation can be coupled with other reactions to form new C―C bonds using reactions studied previously. Predict the product of the following series of reactions.

(a)

The intermediates for the Swern oxidation, a reaction introduced in Section 13.9.4, are shown. Provide the arrow-pushing mechanism that rationalizes the formation of each intermediate and the final product(s).

What product is obtained from the reaction of each of the following alcohols with

a. H₂CrO₄?

1. 3-pentanol

2. 1-pentanol

3. 2-methyl-2-pentanol

What product is obtained from the reaction of each of the following alcohols with

c. the regents required for a Swern oxidation?

1. 3-pentanol

2. 1-pentanol

3. 2-methyl-2-pentanol

Predict the major products of the following reactions.

(c)

Which of the following compounds would give a positive Tollens test? (Remember that the Tollens test involves mild basic aqueous conditions.)

(d) CH₃CH₂CH₂CH₂CH(OH)OCH₃

(e) CH₃CH₂CH₂CH₂CH(OCH₃)₂

(f)

The following reaction involves a starting material with a double bond and a hydroxy group, yet its mechanism resembles a pinacol rearrangement. Propose a mechanism, and point out the part of your mechanism that resembles a pinacol rearrangement.