EBK A SMALL SCALE APPROACH TO ORGANIC L
EBK A SMALL SCALE APPROACH TO ORGANIC L
4th Edition
ISBN: 9781305446021
Author: Lampman
Publisher: CENGAGE LEARNING - CONSIGNMENT
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Chapter 12, Problem 7Q
Interpretation Introduction

Interpretation:

The mechanism for the acid-catalyzed esterification of acetic acid with isopentyl alcohol needs to be explained.

Concept Introduction:

Ester is an organic compound with the general formula RCOOR. It can be formed by the reaction of carboxylic acid with alcohol in the presence of acidic medium. This reaction is called as esterification reaction. The esterification reaction of acetic acid with isopentyl alcohol forms isopentyl acetate. The chemical equation can be written as:

  CH3COOH +  (CH3)2-CH2-CH2-OHCH3COOCH2CH2CH(CH3)2+H2O

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2. Please consider the two all 'cis' isomers of trimethylcyclohexane drawn below. Draw the two chair conformers of each stereoisomer below (1 and 2) and calculate their torsional interaction energies in order to identify the lower energy conformer for each stereoisomer. Based on your calculations, state which of the two stereoisomers 1 and 2 is less stable and which is more stable. [1,3-diaxial CH3 CH3 = 3.7kcal/mol; 1,3-diaxial CH3 H = 0.88kcal/mol; cis-1,2 (axial:equatorial) CH3 CH3 = 0.88kcal/mol; trans-1,2-diequatorial CH3 CH3 = 0.88kcal/mol) all-cis-1,2,3- 1 all-cis-1,2,4- 2
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What is the mechanism by which the 1,4 product is created?  Please draw it by hand with arrows and stuff.
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