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)

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Chapter1: Chemical Foundations
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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. 

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)
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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