The optically active (2R)-2-phenyl-2-butanol reacts in hydrochloric acid to form haloalkanes and alkenes. The substitution reaction is reported to occur with 100% racemization. Give the structures of the enantiomers that form during the substitution and indicate how much of each is formed. Propose a mechanism for the substitution reaction to yield the R product. What reagents would you use to achieve 100% retention of configuration. Two geometric isomers are obtained during the elimination reaction. Explain mechanistically which alkene will be the main product.
The optically active (2R)-2-phenyl-2-butanol reacts in hydrochloric acid to form haloalkanes and alkenes. The substitution reaction is reported to occur with 100% racemization. Give the structures of the enantiomers that form during the substitution and indicate how much of each is formed. Propose a mechanism for the substitution reaction to yield the R product. What reagents would you use to achieve 100% retention of configuration. Two geometric isomers are obtained during the elimination reaction. Explain mechanistically which alkene will be the main product.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section8.7: Radical Autoxidation
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The optically active (2R)-2-phenyl-2-butanol reacts in hydrochloric acid to form
- Give the structures of the enantiomers that form during the substitution and indicate how much of each is formed.
- Propose a mechanism for the substitution reaction to yield the R product.
- What reagents would you use to achieve 100% retention of configuration.
- Two geometric isomers are obtained during the elimination reaction. Explain mechanistically which alkene will be the main product.
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