13. Alcohols and Carbonyl Compounds

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)