Chapter 20.SE, Problem 47AP

Interpretation Introduction

a) LiAlH₄, then H₃O⁺

Interpretation:

The product produced when p-methylbenzoic acid is treated with LiAlH₄ and then with H₃O⁺ is to be predicted.

Concept introduction:

Carboxylic acids get reduced to primary alcohols when treated with LiAlH₄.

To predict:

The product produced when p-methylbenzoic acid is treated with LiAlH₄ and then with H₃O⁺.

Interpretation Introduction

b) N-Bromosuccinimide in CCl₄

Interpretation:

The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl₄ is to be predicted.

Concept introduction:

N-bromosuccinimide in CCl₄ is used for introducing a Br in the benzyl carbon.

To predict:

The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl₄.

Interpretation Introduction

c) CH₃MgBr in ether, then H₃O⁺

Interpretation:

The product produced when p-methylbenzoic acid is treated with CH₃MgBr and then with H₃O⁺ is to be predicted.

Concept introduction:

Grignard reagents will react with the carboxyl hydrogen to yield alkanes.

To predict:

The product produced when p-methylbenzoic acid is treated with CH₃MgBr and then with H₃O⁺.

Interpretation Introduction

d) KMnO₄, H₃O⁺

Interpretation:

The product produced when p-methylbenzoic acid is treated with KMnO₄ in the presence of H₃O⁺ is to be predicted.

Concept introduction:

When treated with KMnO₄ in the presence of H₃O⁺, the side chain in aromatic compounds is oxidized to carboxyl group.

To predict:

The product produced when p-methylbenzoic acid is treated with KMnO₄ in the presence of H₃O⁺.