13. Alcohols and Carbonyl Compounds

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

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

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

A chemist attempted to oxidize a primary alcohol to a carboxylic acid using chromic acid. The product shown was obtained as a major component in the mixture. Suggest an arrow-pushing mechanism that accounts for its formation. [Think about what chromic acid would normally do to a phenol and make a list of bonds formed and bonds broken.]

Predict the product of the following oxidation reactions.

(d)

Predict the product of the following reactions.

(b)

Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.

(b)

Though ketones, like aldehydes, are in equilibrium with a hydrated form, they cannot be further oxidized. Why?

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

(a)

Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.

(a)

Unfortunately, the use of NMO creates an additional green chemistry problem. What is the problem and how might it be solved?

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O. If no reaction occurs, write 'no reaction.'  

(a)