Question

Identify the reagents a–c in the following scheme:

Short answer

a is$\mathrm{H}{}_2\mathrm{O}/{\mathrm{H}}^{+}$

b is HBr

c is${\left({\mathrm{CH}}_3\right)}_2\mathrm{CuLi}$

Step-by-step solution

Alkene to alcohol conversion

Markovnikov's rule: Alkenes react with water in the presence of acid as a catalyst to form alcohols. In the case of unsymmetrical alkenes, OH is added to the carbon, having fewer hydrogen atoms.

Alcohol to alkyl halide conversion

Alcohol, when reacting with HX where X is a halide, it results in the formation of alkyl halides.

Alkyl halide to methyl alkyl conversion

Corey-House synthesis is a reaction that involves the reaction of a lithium divinylcuprate with an alkyl halide to form a new alkane.

Reagents used

• Step1: As alkene to alcohol conversion is occurring$\mathrm{H}{}_2\mathrm{O}/{\mathrm{H}}^{+}$is used here.
• Step 2: As alcohol to alkyl bromide conversion occurs, HBr is used as a reagent.
• Step 3: As alkyl halide to methyl, alkyl conversion is used as a reagent for methyl addition.