Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 18, Problem 26P
Interpretation Introduction

Interpretation:

Each of the given compounds is to be synthesized from diethyl malonate or ethyl acetoacetate and any other organic and inorganic reagents.

Concept Introduction:

βdicarbonyl compound can be converted into enolate ions in the presence of sodium ethoxide.

▸ Alkylation in the βdicarbonyl compound is a SN2 reaction.

▸ Decarboxylation of βketoacid takes place readily in the presence of heat.

▸ LDA stands for lithium disopyramide. It is a strong base.

▸ In Sn2 reaction, one bond is broken and one bond is formed. In Sn2 reaction, the nucleophile attacks on the less sterically hindered carbon.

▸ Reduction of a carboxylic acid into alcohol occurs in the presence of reducing agent LiAlH4.

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3. Name this ether correctly. H₁C H3C CH3 CH3 4. Show the best way to make the ether in #3 by a Williamson Ether Synthesis. Start from an alcohol or phenol. 5. Draw the structure of an example of a sulfide.
1. Which one(s) of these can be oxidized with CrO3 ? (could be more than one) a) triphenylmethanol b) 2-pentanol c) Ethyl alcohol d) CH3 2. Write in all the product(s) of this reaction. Label them as "major" or "minor". 2-methyl-2-hexanol H2SO4, heat
3) Determine if the pairs are constitutional isomers, enantiomers, diastereomers, or mesocompounds. (4 points)

Chapter 18 Solutions

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