ORGANIC CHEM PRINT STUDY GDE & SSM
ORGANIC CHEM PRINT STUDY GDE & SSM
4th Edition
ISBN: 9781119810650
Author: Klein
Publisher: WILEY
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Chapter 13, Problem 53ASP
Interpretation Introduction

Interpretation: The major product of the following reaction needs to be determined.

  ORGANIC CHEM PRINT STUDY GDE & SSM, Chapter 13, Problem 53ASP

Concept introduction: The nucleophilic attack on epoxide takes place at a more substituted position due to a more partial positive character. The reaction follows the SN2 mechanism. The product formed has an inversion of configuration.

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Predict the major organic product(s) of the following reactions. Indicate which of the following mechanisms is in operation: SN1, SN2, E1, or E2.
(c) (4pts) Mechanism: heat (E1) CH3OH + 1.5pts each _E1 _ (1pt) Br CH3OH (d) (4pts) Mechanism: SN1 (1pt) (e) (3pts) 1111 I H 10 Ill!! H LDA THF (solvent) Mechanism: E2 (1pt) NC (f) Bri!!!!! CH3 NaCN (3pts) acetone Mechanism: SN2 (1pt) (SN1) -OCH3 OCH3 1.5pts each 2pts for either product 1pt if incorrect stereochemistry H Br (g) “,、 (3pts) H CH3OH +21 Mechanism: SN2 (1pt) H CH3 2pts 1pt if incorrect stereochemistry H 2pts 1pt if incorrect stereochemistry
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