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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Part II. xiao isolated a compound TAD (Ca H 10 N₂) from tobacco and obtained its IR spectrum. Xiao proposed a chemical structure shown below: % Transmittance 4000 3500 3000 2500 2000 Wavenumber (cm-1) 1500 1000 (a) Explain why her proposed structure is inconsistent with the IR spectrum obtained (b) TAD exists as a tautomer of the structure xiao proposed. Draw the structure and explain why it is more compatible with the obtained spectrum. (C) what is the possible source for the fairly intense signal at 1621cm1
AE>AE₁ (Y/N) AE=AE₁ (Y/N) AE

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Organic Chemistry

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