Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Concept explainers

Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and…
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic…
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction…
Question

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) Which product predominates—the product of inversion or the product of retention of configuration?

(c) Suggest an explanation for this phenomenon.

Br OH H2O 1-bromo-1-phenylpropane 1-phenylpropan-1-ol observed [a] = +5.0 optically pure S isomer, [a] = -48
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Transcribed Image Text:Br OH H2O 1-bromo-1-phenylpropane 1-phenylpropan-1-ol observed [a] = +5.0 optically pure S isomer, [a] = -48
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