ORGANIC CHEMISTRY BOOK& SG/SM
ORGANIC CHEMISTRY BOOK& SG/SM
6th Edition
ISBN: 9781264094493
Author: SMITH
Publisher: MCG
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Chapter 16.9, Problem 22P
Interpretation Introduction

(a)

Interpretation: All resonance structures for the carbocation of given compound formed by ortho attack of the electrophile +NO2 are to be drawn. The resonance structures are to be labeled as stable or unstable.

Concept introduction: Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.

Interpretation Introduction

(b)

Interpretation: All resonance structures for the carbocation of given compound formed by ortho attack of the electrophile +NO2 are to be drawn. The resonance structures are to be labeled as stable or unstable.

Concept introduction: Resonance structure is a blend of two or more Lewis structures. Resonance structures are represented by a double headed arrow between the structures.

Interpretation Introduction

(c)

Interpretation: All resonance structures for the carbocation of given compound formed by ortho attack of the electrophile +NO2 are to be drawn. The resonance structures are to be labeled as stable or unstable.

Concept introduction: Most of the organic structures cannot be represented using single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures.

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4. Draw all resonance structures for the carbocation formed by ortho attack of the electrophile +NO2 on each starting material. Label any resonance structures that are especially stable or unstable. C(CH3)3 LOH CHO a. b. С.
For each of the reactions indicate which reactant is the nucleophile and which is the electrophile.
Rank the species in each group in order of increasing nucleophilicity. a. CH,, "OH, "NH2 b. H20, OH, "SH in CH3OH c. CH,CH2S", CH;CH2O¯, CH;COO" in CH3OH d. CH3NH2, CH3SH, CH;OH in acetone e. "OH, F", CI" in acetone f. HS, F", CI in CH3OH

Chapter 16 Solutions

ORGANIC CHEMISTRY BOOK& SG/SM

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