Question

Draw the product formed when ${\mathbf{\left(}{\mathbf{CH}}_{\mathbf{3}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}\mathbf{\right)}}_{\mathbf{2}}\mathbf{}\mathbf{CuLi}$is treated with each compound. In some cases, no reaction occurs.

Short answer

The products formed when ${\left({\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\right)}_2\mathrm{CuLi}$ is treated with each compound are shown below:

Step-by-step solution

 Step 1: Use of organocuprate

You can useorganocuprate in many nucleophilic substitution reactions to get products such as aldehydes and ketones.

They attack the electrophilic carbon center of any acid chloride structures where chlorine is a powerful leaving group and also take part in a 1,4-addition reaction.

Cases where the reaction is possible

The reaction with organocuprate is possible when the leaving group, like halides, present in acid derivative compounds is facile enough to proceed with the reaction. In case of compound b, no reaction ocuurs.

Besides, the reaction takes place in unsaturated carbonyl compounds where 1,4-addition is possible.