13. Alcohols and Carbonyl Compounds

Predict the major products of the following reactions.

(d)

Predict the products of the reactions of the following compounds with:

1. chromic acid or excess sodium hypochlorite with acetic acid.

2. PCC or NaOCl (1 equivalent) with TEMPO.

f. 1-phenylpropan-1-ol

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)

Draw a mechanism for the following oxidation reactions.

(b)

Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.

b. Tollens reagent

Identify the aromatic product that would result from the oxidation of the triol with an excess of PCC.

Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.

a. chromic acid

b. PCC (pyridinium chlorochromate)

c. sodium hypochlorite/acetic acid

In Assessment 13.48, identify the individual step that represents the general mechanism for all alcohol oxidation reactions.

Every oxidation is accompanied by a reduction. Identify the species that is reduced in the Swern oxidation in Assessment 13.48.

Predict the products of the reactions of the following compounds with:

1. chromic acid or excess sodium hypochlorite with acetic acid.

2. PCC or NaOCl (1 equivalent) with TEMPO.

a. cyclohexanol

b. 1-methylcyclohexanol

c. cyclopentylmethanol

Assessment 24.22 asked why meta-dihydroxybenzene could not be oxidized to meta-quinone. The attempted oxidation instead gives rise to three different quinone products. Suggest a mechanism for the formation of each.

Oxidation of a phenol derivative produces the lactone shown. Provide an arrow-pushing mechanism that rationalizes this outcome.

Tertiary (3°)alcohols are not oxidized by chromic acid. Why?

(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 following oxidation reactions.

(d)