Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 18.4, Problem 4P
Interpretation Introduction

Interpretation: It is to be identified if catalytic hydrogenation can be used to reduce a carboxylic acid to a primary alcohol in the first step of the sequence RCO2HRCH2OHRCHO.

Concept introduction: The addition of H2 to a molecule in the presence of a catalyst is known as catalytic hydrogenation reaction. This process is used to reduce aldehydes and ketones to alcohols.

Lithium aluminum hydride and sodium borohydride are strong reducing agents. They are inorganic compounds which are used as the reducing agents in organic synthesis. They used for the conversion of carboxylic acids, aldehydes and ketones into primary and secondary alcohols.

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(a) What is the structure of C, which is formed by oxy-Coperearrangement of B with NaOEt? (b) Draw a stepwise mechanism for theconversion of C to the bicyclic alcohol D.
Bromoetherification, the addition of the elements of Br and OR to adouble bond, is a common method for constructing rings containingoxygen atoms. This reaction has been used in the synthesis of thepolyether antibiotic monensin (Problem 18.34). Draw a stepwisemechanism for the following intramolecular bromoetherification reaction.
An allylic alcohol contains an OH group on a carbon atom adjacent to aC—C double bond. Treatment of allylic alcohol A with HCl forms amixture of two allylic chlorides, B and C. Draw a stepwise mechanismthat illustrates how both products are formed.

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Organic Chemistry - Standalone book

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