13. Alcohols and Carbonyl Compounds

What are the products of the following reactions?

a.

b.

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(c)

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(e)

Identify compounds A and B:

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?

Predict the products 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:

f.

Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.

(c)

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

a.

b.

Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

(a)

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.

Identify A through H

Show how this 1° alcohol can be made from the following:

(b) formaldehyde

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

b.