13. Alcohols and Carbonyl Compounds

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.

Predict the products formed by periodic acid cleavage of the following diols.

(c)

(d)

Predict the major products of the following reactions, including stereochemistry where appropriate.

(c) cyclooctanol + NaOCl/HOAC

(d) cyclopentylmethanol + CrO₃·pyridine·HCl

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na₂Cr₂O₇/H₂SO₄, (2) PCC

c. 4-hydroxydecanal

Give the structure of the principal product(s) when each of the following alcohols reacts with (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

c. 4-hydroxydecanal