EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393543971
Author: KARTY
Publisher: VST
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Chapter 22, Problem 22.54P
Interpretation Introduction

Interpretation:

Compounds A-G in the given synthesis scheme are to be identified.

Concept introduction:

Friedel craft acylation is the electrophilic substitution reaction in the presence of Lewis acid. In the haloform reaction, acetyl group is converted into haloform or carboxyl group through exhaustive halogenation. To convert the carboxylic group into acid chloride, thionyl chloride is used.

Nitration is the aromatic electrophilic substitution reaction in the presence of concentrated nitric acid and concentrated sulfuric acid. In this reaction, nitronium ion NO2+ are attached to the aromatic ring and acts as an electrophile. LiAlH4 is a strong reducing agent, it convert the carbonyl carbon into the corresponding alcohol, amide or nitrile to amine.

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Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)
3. What starting material would you use to synthesize 3-hydroxypentanoic acid using a NaBH4 reduction?
1. Give stereochemical (Fischer projection) formulas for all (but no extras) the stereoisomers that could theoretically form during the reduction of a. the carbonyl group of 2-methyl-3--pentanone b. both carbonyl groups of 2,4-pentanedione (careful!) 2. Predict the products of the reduction of O=CCH2CH2CH2C=O with a. LiAlH4 b. NaBH4 CH3 OH

Chapter 22 Solutions

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M

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