13. Alcohols and Carbonyl Compounds

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:

A dibromide loses only one bromine when it reacts with sodium hydroxide. The dibromide forms toluene (C₆H₅-CH₃) when it reacts with magnesium shavings in ether followed by treatment with dilute acid. Give possible structures for the dibromide.

What is the major product of each of the following reactions?

c.

d.

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:

e.

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:

d.

Identify A through H

Fill in the boxes with the appropriate reagents:

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

a.

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

c.