More stable species in given pair has to be identified. Concept Introduction: In an S N 2 reaction, relative stability of alkyl halide is primary > secondary > tertiary. The tertiary carbocation is the most stable. The primary carbanion is the most stable. Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

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Answer 1

Question

Chapter 9, Problem 86P

(a)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

The tertiary carbocation is the most stable. The primary carbanion is the most stable. Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(b)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(c)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(d)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(e)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(f)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(g)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

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Answer 2

Question

Chapter 9, Problem 86P

(a)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

The tertiary carbocation is the most stable. The primary carbanion is the most stable. Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(b)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(c)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(d)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(e)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(f)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(g)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

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Answer 3

Question

Chapter 9, Problem 86P

(a)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

The tertiary carbocation is the most stable. The primary carbanion is the most stable. Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(b)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(c)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(d)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(e)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(f)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(g)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

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Answer 4

Question

Chapter 9, Problem 86P

(a)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

The tertiary carbocation is the most stable. The primary carbanion is the most stable. Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(b)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(c)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(d)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(e)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(f)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(g)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

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Answer 5

Chapter 9, Problem 86P

(a)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

The tertiary carbocation is the most stable. The primary carbanion is the most stable. Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(b)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(c)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(d)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(e)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(f)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

(g)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 6

Chapter 9, Problem 86P

(a)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

The tertiary carbocation is the most stable. The primary carbanion is the most stable. Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 7

Chapter 9, Problem 86P

(a)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

The tertiary carbocation is the most stable. The primary carbanion is the most stable. Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 8

(b)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 9

(b)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 10

(c)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 11

(c)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 12

(d)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 13

(d)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 14

(e)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 15

(e)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 16

(f)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 17

(f)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 18

(g)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 19

(g)

Interpretation Introduction

Interpretation:

More stable species in given pair has to be identified.

Concept Introduction:

In an S_N2 reaction, relative stability of alkyl halide is primary > secondary > tertiary.

Resonance allows for delocalization, in which the overall energy of a molecule is lowered since its electrons occupy a greater volume, molecules that experience resonance are more stable than those that do not.

Answer 20

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Answer 21

Expert Solution & Answer

Answer 22

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Answer 23

Ch. 9.1 - Prob. 3P Ch. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.1 - Prob. 8P Ch. 9.2 - Prob. 9P Ch. 9.2 - Prob. 10P Ch. 9.2 - Prob. 11P Ch. 9.2 - Prob. 12P Ch. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 15P

Solution Summary: The author explains that in an S N 2 reaction, relative stability of alkyl halide is primary > secondary > tertiary, and resonance allows for delocalization.

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Chapter 9 Solutions