Question

What reagents are needed to convert 2-methylpropene $[\left({\mathrm{CH}}_3\right)C={\mathrm{CH}}_2]$to each compound? More than one step may be required.

a.

b.

c.

Short answer

Answer

a.

b.

c.

Step-by-step solution

Cyclopropanes

A new C-C bond is formed via the reaction of alkenes with carbene intermediates to form the corresponding cyclopropanes.

Finding reagents

The following reagents are used to convert 2-methylpropene to the given compounds.

a. 2-Methylpropene reacts with trichloromethane in the presence of potassium tert-butoxide to form the given cyclopropane.

Reaction with trichloromethane and potassium-tert-butoxide

b. 2-Methylpropene reacts with tribromomethane in the presence of potassium tert-butoxide to form the given cyclopropane.

Reaction with tribromomethane and potassium-tert-butoxide

c. 2-Methylpropene reacts with lithium dimethyl cuprate to form the given cyclopropane.

Reaction with lithium dimethyl cuprate