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?

(d)

Why are $\mathrm{aldehydes}$ generally more reactive than $\mathrm{ketones}$ toward nucleophilic addition reactions?

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

(c)

(d)

Which of the following compounds could be used as a nucleophile in an aldol reaction?

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

(b)

Show how you would accomplish the following syntheses.

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

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

(b)

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)