Question

Question 15 Provide the reagents necessary to carry out the following conversion, OH 0 1. Cl/AlCl3 2.0₃ 1. Cly/FeCl3 2. H202 01. CH3CI/FeCl3 2. HNO3/H2504 1. Cl2, light (hv) 2. Na2Cr207/H2SO4/H20 1. Cl./FeCla 2. Na2Cr207/H2SO4/H20 By accessing this Question Assistance, you will learn while you earn points based Point Potential Policy set by your instructor.

Answer 1

Answer - We are given cumene as substrate and 4-chlorobenzoic acid as a product and asked for the reagent required for this conversion.
The chloro group is in the para position with respect to the carboxylic acid group (-COOH) in a product, since we need to first attach the chloro group and then carboxylic acid group

If we first convert the alkyl group to carboxylic acid, then the incoming chloro group will go at meta position, but we needed it on the para.
Thus, there is the first reaction is chlorination of benzene ring and then oxidation of alkyl to gets carboxylic acid respectively. The chlorination of benzene done with Cl₂ in FeCl₃ and oxidation of propyl group to carboxylic acid is done by Na₂Cr₂O₇ /H₂SO₄ / H₂O

The reaction and reagents are as follows.

1. Cl/FeCl3 OH 2. Na,Cr,O,/ H2SO4/H,0 cm 4-chlorobenzoic acid cumene

1. Cl/FeCl3 OH 2. Na,Cr,O,/ H2SO4/H,0 cm 4-chlorobenzoic acid cumene