ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
4th Edition
ISBN: 9781119745105
Author: Klein
Publisher: WILEY
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Chapter 6, Problem 61IP

(a)

Interpretation Introduction

Interpretation:

The curved arrows for each step of the mechanism must be drawn and the sequence of arrow pushing patterns must be identified.

Concept Introduction :

The curved arrow shows the electron flow; and thereby, it shows bond breaking and new bond formation. The alpha hydrogen of ketones is acidic due to electron withdrawing nature of the keto group.

(b)

Interpretation Introduction

Interpretation:

For the conversion of 4 to 5 the electrophilic and nucleophilic centers must be identified with the help of resonance.

Concept Introduction :

Electrophilic centers are those where there is low electron density. Nucleophilic centers are those where there is higher electron density.

(c)

Interpretation Introduction

Interpretation:

Configuration of the newly formed chiral center during conversion of 4 to 5 must be determined. Why the other possible configuration is not observed must be explained.

Concept Introduction :

The configuration of a chiral center depends on the three dimensional orientations and priorities of different groups. Priorities of those groups can be determined using CIP (Cahn-Ingold-Prelog) priority rules according to which higher is the atomic number, higher is the priority.

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Assign R or S to all the chiral centers in each compound drawn below porat bg 9 Br Br
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