13. Alcohols and Carbonyl Compounds

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

(a) CH₃CH(OH)CH(OH)CH₃

(b)

Predict the product of the oxidation reactions shown.

(a)

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

Although trans-diols in rings cannot be cleaved using HIO₄ acyclic trans-diols can. Explain this discrepancy.

Predict the product of the following oxidation reactions.

(b)

δ-Hydroxyaldehydes are in equilibrium with their hemiacetal form. Predict the product that would form upon treatment of the hemiacetal with Dess–Martin periodinane.

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

Fill in the missing reactant, reagent, or product for each of the following oxidation reactions. react similarly to chromic acid

(d)

Predict the product of the following reactions.

(a)

Draw a mechanism for the following oxidation reactions.

(a)

Predict the product of the following oxidation reactions.

(a)

Propose a mechanism to explain how dimethyl sulfoxide and oxalyl chloride react to form the dimethylchlorosulfonium ion used as the oxidizing agent in the Swern oxidation.

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

(a) CH₃CH₂CH₂COCH₃

(b) CH₃CH₂CH₂CH₂CHO

(c) CH₃CH=CHCH=CHOH

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

b. Tollens reagent

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

g. Tollens reagent