Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 5.SE, Problem 70AP
Interpretation Introduction
Interpretation:
The light induced reaction of (S)-1-chloro-2-methylbutane is to be explained.
Concept introduction:
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2,3-Dibromoprop-1-ene (C3H4Br2) has four H atoms. Suppose that any of these H atoms can be replaced by a Cl atom to
yield a molecule with the formula C3H3Br,Cl. (a) Identify two H atoms where this substitution would yield constitutional
isomers of C3H3Br,CI; (b) enantiomers of C3H3Br,Cl; (c) diastereomers of C3H3Br,Cl.
H
нн
H
Br
Br
2,3-Dibromoprop-1-ene
(b) Draw the structural formula for each of the following compounds.
(i) 2,2,3-trimethylpentan-3-ol(ii) 2-methyl-3-phenylbut-2-enal(iii) 5-chloro-2-methylheptan-3-ol
Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide.
(a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds.
(b) Then analyze the stereochemistry of the product.
racemic
chiral
achiral
(1R, 3S)
(1R, 3R)
(1S, 3S)
Chapter 5 Solutions
Organic Chemistry
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