ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
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Question
Chapter 17, Problem 35P
Interpretation Introduction
Interpretation:
The stereochemical configuration of the propranolol formed by the given sequence is to be stated.
Concept introduction:
If the epoxide is unsymmetrical, then the anionic nucleophile will attack the less-hindered carbon atom of the ring.
If the reaction conditions are acidic, then the reaction will occur at the more substituted carbon atom.
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Students have asked these similar questions
d) Identify one compound that is expected to have identical physical properties as structure II.
(e) Other than structures III and VI, identify a stereoisomer with a different boiling point from that of structure II.
(f) Other than structures IV, identify one diastereomer of structure I.
(g) How many stereoisomers may be derived from structure V?
In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1- phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Whichproduct predominates—the product of inversion or the product of retention of conguration? (c) Suggest an explanation for this phenomenon.
In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one
enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1-phenyl-1-propanol.
(a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates-the
product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon.
H Br
он
H20
1-bromo-1-phenylpropane
1-phenyl-1-propanol
observed [a) = +5.0
optically pure S isomer, [a] =-48
%3D
Chapter 17 Solutions
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
Ch. 17.1 - Prob. 1PCh. 17.2 - The heats of combustion of 1, 2-epoxybutane...Ch. 17.3 - Prob. 3PCh. 17.4 - Prob. 4PCh. 17.5 - Prob. 5PCh. 17.6 - Problem 17.6 (a) Write equations describing two...Ch. 17.6 - Problem 17.7 Only one combination of alkyl halide...Ch. 17.6 - Prob. 8PCh. 17.8 - Prob. 9PCh. 17.8 - Prob. 10P
Ch. 17.9 - Prob. 11PCh. 17.10 - Problem 17.12 Classify the bromohydrins formed...Ch. 17.11 - Prob. 13PCh. 17.11 - Prob. 14PCh. 17.12 - Prob. 15PCh. 17.12 - Prob. 16PCh. 17.14 - Prob. 17PCh. 17.15 - Prob. 18PCh. 17.16 - Prob. 19PCh. 17.17 - Problem 17.20 There is another oxygen-stabilized...Ch. 17 - Prob. 21PCh. 17 - Many ethers, including diethyl ether, are...Ch. 17 - Although epoxides are always considered to have...Ch. 17 - The name of the parent six-membered...Ch. 17 - Prob. 25PCh. 17 - Prob. 26PCh. 17 - Prob. 27PCh. 17 - Prob. 28PCh. 17 - Prob. 29PCh. 17 - Given that: does the product of the analogous...Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - Prob. 36PCh. 17 - When (R)-(+)-2-phenyl-2-butanol is allowed to...Ch. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Write a mechanism for the following reaction.Ch. 17 - Prob. 41PCh. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - Prob. 44PCh. 17 - Prob. 45PCh. 17 - Prob. 46DSPCh. 17 - Prob. 47DSPCh. 17 - Prob. 48DSPCh. 17 - Prob. 49DSPCh. 17 - Epoxide Rearrangements and the NIH Shift This...Ch. 17 - Epoxide Rearrangements and the NIH Shift This...
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