ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
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.
2. A benzene ring alters the reactivity of a neighboring group in the so-called "benzylic" position, similarly to how a double bond alters the reactivity of groups in the "allylic" position. R .R allylic position benzylic position Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.
Rank the nucleophiles in each group in order of increasing nucleophilicity. a.−OH, −NH2, H2O b.−OH, Br−, F− (polar aprotic solvent) c.H2O, −OH, CH3CO2−

Chapter 16 Solutions

ORGANIC CHEMISTRY

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