21. Aldehydes and Ketones: Nucleophilic Addition

Provide the chemical steps necessary for the following synthesis.

Provide the chemical steps necessary for the following synthesis.

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(b)

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(e)

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

(d) ethylene glycol and p-toluenesulfonic acid

Propose mechanisms for the following reactions.

(d)

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.

(a)

Predict the major products of the following reactions:

(d)

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

(d)

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(d)

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.

(b)

Rationalize the difference in Kₑq for the following reactions. Be sure to account for both ∆S and ∆H.

1. Analyze ∆S and ∆H differences." width="737">