Question

Devise a synthesis of the given alcohol from benzene, organic alcohols having four or fewer carbons, and any needed inorganic reagents.

Short answer

Benzene reacts with tertiary butyl bromine to form tertiary butyl benzene which on Friedel-Crafts reaction followed by Grignard reaction gives the final product.

Step-by-step solution

Aromatic synthesis

Synthesis of polycyclic compounds or benzene derivatives with benzene as starting material is called aromatic synthesis.

Benzene is used because of its reactivity towards many substitution reactions.

Organic or inorganic reagents are used for synthesis based on yield and reactivity.

Grignard reaction

The reaction of a carbanion formed from organomagnesium reagent with electrophilic carbon part of a polar bond is called a Grignard reaction.

The C-Mg bond contains electropositive magnesium and electronegative carbon. Therefore, a cleaving C-Mg bond produces a carbanion.

Grignard reaction is used to extend the carbon chain in organic synthesis.

Synthesis of the given compound from benzene

Benzene reacts with tertiary butyl bromine to form tertiary butyl benzene which on Friedel-Crafts reaction with acid chloride followed by Grignard reaction with methyl magnesium bromide gives the final product.

Stepwise synthesis mechanism