13. Alcohols and Carbonyl Compounds

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

(a)

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

(d)

Based on the analysis you used in Assessment 17.3, which carbonyl would you expect to react most quickly with a nucleophile?

(a)

Why is a ketone more reactive/electrophilic than an ester?

Nucleophilic addition to the α,β-unsaturated ketone shown can occur at either C₂ or C₄. Why?

a. Could a nucleophile ever add to C₃?

b. Why or why not?

What product is formed when 3-methyl-2-cyclohexenone reacts with each of the following reagents?

c. HBr

d. CH₃CH₂SH

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(a)

Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents

(c)

(d)

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(c)

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(b)

Show how you would accomplish the following syntheses.

b. cyclopentanecarbaldehyde → 2-cyclopentyl-2-hydroxyacetic acid

Propose a mechanism for the following reactions:

a.

Predict the product of the following aldehyde and ketone addition reactions.

(b)