13. Alcohols and Carbonyl Compounds

What are the products of the following reactions?

a.

b.

What are the products of the following reactions?

b.

What are the products of the following reactions? Show all stereoisomers that are formed.

a.

b.

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

a. CH₃MgBr followed by H₃O⁺

b. (CH₃CH₂)₂CuLi followed by H₃O⁺

The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an α-bromo ester with zinc.

Describe how each of the following compounds can be prepared, using a Reformatsky reaction:

a.

Using bromocyclohexane as a starting material, how could you synthesize the following compounds?

a.

What alcohols are formed from the reaction of ethylene oxide with the following organocuprates followed by the addition of acid?

b. (CH₃CH=CH)₂CuLi

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

(d) cyclopentyl propyl ketone

Show how you would accomplish the following synthetic

conversions by adding an organolithium reagent to an acid.

(c) pentanoic acid → heptan-3-one

Predict the products of the following reactions:

(c)

(d)

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(d) phenylacetic acid → 3,3-dimethyl-1-phenylbutan-2-one

Propose structures for intermediates and products (A) through (D).

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

f. 1-(phenylmethyl)cyclohexanol

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(a)

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(b)