Organic Chemistry: Principles And Mechanisms
Organic Chemistry: Principles And Mechanisms
2nd Edition
ISBN: 9780393630756
Author: KARTY, Joel
Publisher: W.w. Norton & Company,
Question
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Chapter 20, Problem 20.18P
Interpretation Introduction

(a)

Interpretation:

Detailed mechanism and major product for the following reaction is to be proposed.

Concept introduction:

LiAlH4 is a strong reducing agent having hydride ion as active electron rich species. Hydride ions are excellent nucleophiles but poor leaving groups. However, they can still react with acids and their derivatives. LiAlH4 can reduce carboxylic acid to primary alcohol due to its greater reactivity while NaBH4 cannot. Carboxylic, which is alike other acid, derivatives undergo proton transfer due to the presence of acidic hydrogen.

Interpretation Introduction

(b)

Interpretation:

Detailed mechanism and major product for following reaction is to be proposed.

Concept introduction:

LiAlH4 is a strong reducing agent having hydride ion as active electron rich species. Hydride ions are excellent nucleophiles but poor leaving groups. However, they can still react with acids and amides in nucleophilic addition-elimination reaction. LiAlH4 can reduce amide to amine without disturbing the carbon backbone of the original compound.

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Chapter 20 Solutions

Organic Chemistry: Principles And Mechanisms

Ch. 20 - Prob. 20.11PCh. 20 - Prob. 20.12PCh. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 20 - Prob. 20.16PCh. 20 - Prob. 20.17PCh. 20 - Prob. 20.18PCh. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Prob. 20.21PCh. 20 - Prob. 20.22PCh. 20 - Prob. 20.23PCh. 20 - Prob. 20.24PCh. 20 - Prob. 20.25PCh. 20 - Prob. 20.26PCh. 20 - Prob. 20.27PCh. 20 - Prob. 20.28PCh. 20 - Prob. 20.29PCh. 20 - Prob. 20.30PCh. 20 - Prob. 20.31PCh. 20 - Prob. 20.32PCh. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Prob. 20.35PCh. 20 - Prob. 20.36PCh. 20 - Prob. 20.37PCh. 20 - Prob. 20.38PCh. 20 - Prob. 20.39PCh. 20 - Prob. 20.40PCh. 20 - Prob. 20.41PCh. 20 - Prob. 20.42PCh. 20 - Prob. 20.43PCh. 20 - Prob. 20.44PCh. 20 - Prob. 20.45PCh. 20 - Prob. 20.46PCh. 20 - Prob. 20.47PCh. 20 - Prob. 20.48PCh. 20 - Prob. 20.49PCh. 20 - Prob. 20.50PCh. 20 - Prob. 20.51PCh. 20 - Prob. 20.52PCh. 20 - Prob. 20.53PCh. 20 - Prob. 20.54PCh. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - Prob. 20.57PCh. 20 - Prob. 20.58PCh. 20 - Prob. 20.59PCh. 20 - Prob. 20.60PCh. 20 - Prob. 20.61PCh. 20 - Prob. 20.62PCh. 20 - Prob. 20.63PCh. 20 - Prob. 20.64PCh. 20 - Prob. 20.65PCh. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 20 - Prob. 20.69PCh. 20 - Prob. 20.70PCh. 20 - Prob. 20.71PCh. 20 - Prob. 20.1YTCh. 20 - Prob. 20.2YTCh. 20 - Prob. 20.3YTCh. 20 - Prob. 20.4YTCh. 20 - Prob. 20.5YTCh. 20 - Prob. 20.6YTCh. 20 - Prob. 20.7YTCh. 20 - Prob. 20.8YTCh. 20 - Prob. 20.9YTCh. 20 - Prob. 20.10YTCh. 20 - Prob. 20.11YTCh. 20 - Prob. 20.12YTCh. 20 - Prob. 20.13YT
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