Ts H,C- S-CI ÓH only geometric isomer OO, (тCРВA) OCH,CH, i) NaH CH,0 CH,0 racemic racemic two enantiomers formed; show stereochemistry for one CrOg, H,SO, (aq)
Ts H,C- S-CI ÓH only geometric isomer OO, (тCРВA) OCH,CH, i) NaH CH,0 CH,0 racemic racemic two enantiomers formed; show stereochemistry for one CrOg, H,SO, (aq)
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Complete the reaction scheme below by filling in missing reagents and/or intermediate products for each step. Please explain.
Transcribed Image Text:Ts
H,C-
S-CI
ÓH
only geometric isomer
OO,
(тCРВA)
OCH,CH,
i) NaH
CH,0
CH,0
racemic
racemic
two enantiomers formed;
show stereochemistry for one
CrOg, H,SO, (aq)
Expert Solution
Step 1
- Tosylation of alcohol by tosyl chloride in the presence of pyridine gives corresponding tosylated product.
- Elimination of tosyl group in the presence of based (ethoxide) give more stable alkene.
- Epoxidation with m-CPBA generates two enantiomeric alcohols, the structure of only one has been shown
- Opening of epoxide under acidic condition occurs from the greater substituted side because of greater stability of carbocation.
- Alkylation of alcohol with ethyl iodide gives ether
- Oxidation of secodary alcohol with chromic acid gives corresponding ketone
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