Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
Question
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Chapter 9.3, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The stereoisomers that are obtained from the given SN1  reaction has to be drawn.

Concept Introduction:

  • Unimolecular nucleophilic substitution reaction in which the reversible ionization of alkyl halide in the presence of aqueous acetone or an aqueous ethyl alcohol provides a carbocation as an intermediate, attacked by the nucleophile to form the product.
  • If the leaving group in SN1  reaction is attached to the asymmetric carbon, a pair of enantiomers will be formed.
  • An enantiomer, also known as an optical isomer, is one of two stereoisomers that are mirror images of each other that are non-superimposable.

(b)

Interpretation Introduction

Interpretation:

The stereoisomers that are obtained from the given SN1  reaction has to be drawn.

Concept Introduction:

  • Unimolecular nucleophilic substitution reaction in which the reversible ionization of alkyl halide in the presence of aqueous acetone or an aqueous ethyl alcohol provides a carbocation as an intermediate, attacked by the nucleophile to form the product.
  • If the leaving group in SN1  reaction is attached to the asymmetric carbon, a pair of enantiomers will be formed.
  • An enantiomer, also known as an optical isomer, is one of two stereoisomers that are mirror images of each other that are non-superimposable.

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7) You want to synthesize 3-methyl-2-pentene from 2-chloro-3-methylpentane. Which reagent would you use? a. HCI, heat b. NH:(aq), 25°C c. CH:CO2NA, CH:CO2H, heat d. CH3CH2ONA, CH3CH2OH, heat e. CН:CH2ОН, heat
Draw the products obtained from the SN2 reaction of a. 2-bromobutane and methoxide ion.          b. (R)-2-bromobutane and methoxide ion. c. (S)-3-chlorohexane and hydroxide ion. d. 3-iodopentane and hydroxide ion.
What stereoisomers are formed in the following reactions? Which stereoisomer is the major product? a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene

Chapter 9 Solutions

Organic Chemistry

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