21. Aldehydes and Ketones: Nucleophilic Addition

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(a)

Draw structures of the following derivatives.

(f) the methyl hemiacetal of formaldehyde

What is the specific rotation of an equilibrium mixture of fructose? (Hint: Recall that the specific rotation of an equilibrium mixture of glucose is +52.7.)

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

(e) phenylhydrazine and weak acid

Draw a mechanism for the reaction of propanoyl chloride with 2 moles of phenylmagnesium bromide.

Show how you would accomplish the following syntheses efficiently and in good yield. You may use any necessary reagents.

(a) acetaldehyde → lactic acid, CH₃CH(OH)COOH

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

(k) sodium cyanide

What are the products of the following reactions?

b.

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

(c) hydroxylamine and weak acid

Give the expected products of the following acid-catalyzed reactions.

(a) acetophenone + methylamine

What are the products of the following reactions?

f.

Predict the major products of the following reactions.

(j)

Which of the following amino acid side chains can form an imine with a substrate?

Propose a mechanism for each of the following reactions:

b.

Depending on the reaction conditions, two different imines of formula C₈H₉N might be formed by the reaction of benzaldehyde with methylamine. Explain, and give the structures of the two imines.