13. Alcohols and Carbonyl Compounds

For each of the following carbonyl addition reactions, would you expect a racemic mixture or a mixture enriched in one stereoisomer? In each case, draw both possible stereoisomeric products.

(a)

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

(a)

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

(c)

What other product is formed in this reaction?

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

f.

What organometallic compound is formed from the reaction of excess methylmagnesium chloride and GaCl₃?

What bromo-substituted compound would be required to react with (CH₂=CH)₂CuLi in order to form each of the following compounds?

b.

What alkyl halide reacts with lithium divinylcuprate [(CH₂=CH)₂CuLi] for the synthesis of each of the following compounds?

a.

b.

Predict the product that would result from the reaction of an organolithium reagent with a ketone when a hydroxyl group is present in the ketone substrate.

The situation shown here is an example where a cuprate is the only organometallic that will allow the product alcohol to be obtained. What is the problem with using a Grignard or an organolithium to attempt the same reaction?

What bromo-substituted compound would be required to react with (CH₂=CH)₂CuLi in order to form each of the following compounds?

c.

What alkyl halide reacts with lithium divinylcuprate [(CH₂=CH)₂CuLi] for the synthesis of each of the following compounds?

c.

d.

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

c.

What are the products of the following reactions?

a.

Identify compounds A and B: