Question

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Provide the reagents necessary to carry out the following conversion. CCH3 Choose the correct reagents for step 1. CH3CH2Cl / AICI Cl2 / AICI Bry/ FeBry CH3CCI / AICI:

Answer 1

Reagents for step 1:

CH3CCI / AICI

Reagents for step 2:

Brz/ FeBry

The benzene ring is meta substituted. Hence, the benzene ring should first have a deactivating group attached in its mono-substituted form. Among Br and CH₃CO, CH₃CO (acetyl) group is a deactivating group. So, the first reaction of benzene should be with acetyl chloride in presence of aluminium chloride catalyst (Friedel-Crafts acylation reaction) to give acetophenone. Then acetophenone will react with bromine in presence of FeBr₃ catalyst to give the meta-bromoacetophenone.

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Correct option:

НО

Phenolic OH is an ortho/para directing group. The para position and one of the ortho positions are sterically crowded. So the Cl will preferably attach to the sterically less crowded ortho position to give the major product.

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Reagent for step 1:

(CH3)2CHCI / AICI

Reagent for step 2:

CH3CH2CCI / AICI

Reagent for step 3:

Zn(Hg) / HCI, A

The benzene ring is para substituted. This implies that in the first step the ring attaches to an activating group. The activating group is isopropyl which attaches to benzene by Friedel-Crafts alkylation reaction. In the next step, the isopropyl benzene reacts with propionyl chloride in Friedel-Crafts acylation reaction to give the para-substituted product. The keto carbonyl group (C=O) is then reduced in Clemmensen reduction reaction to give the product.