Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 22.2, Problem 6P
Interpretation Introduction

Interpretation: A stepwise mechanism for the given reaction of benzaldehyde (C6H5CHO) with heptanal (CH3CH2CH2CH2CH2CH2CHO) is to be drawn.

Concept Introduction: Aldol reaction is the condensation reaction of the organic chemistry. In this reaction an enolate ion or an enol reacts with the carbonyl compound that leads to the formation of β-hydroxyaldehyde or β-hydroxyketone which on further dehydration gives the conjugated enone. It is necessary that the carbonyl compound must contain at least one αhydrogen atom to undergo aldol reaction.

The crossed aldol reaction takes place between the two different carbonyl compounds that is between two different aldehydes or two different ketones or one aldehyde and one ketone. The crossed aldol reaction takes place only if the carbonyl compound contains an acidic αhydrogen atom.

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2-Pentylcinnamaldehyde, commonly called flosal, is a perfume ingredient with a jasmine-like odor. Flosal is an a,B-unsaturated aldehyde made by a crossed aldol reaction between benzaldehyde (CsH;CHO) and heptanal (CH,CH,CH2CH,CH,CH2CHO), followed by dehydration. Draw a stepwise mechanism for the following reaction that prepares flosal. CHO OH CgH;CHO CHO + Hо H20 flosal (perfume component)
2-Pentylcinnamaldehyde, commonly called flosal, is a perfume ingredient with a jasminelike odor. Flosal is an α,β-unsaturated aldehyde made by a crossed aldol reactionbetween benzaldehyde (C6H5CHO) and heptanal (CH3CH2CH2CH2CH2CH2CHO), followed by dehydration. Draw a stepwise mechanism for the following reaction that prepares flosal.
β-D-Glucose, a hemiacetal, can be converted to a mixture of acetals on treatment with CH3OH in the presence of acid. Draw a stepwise mechanism for this reaction. Explain why two acetals are formed from a single starting material.

Chapter 22 Solutions

Organic Chemistry (6th Edition)

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