Intermediate carbocation should be drawn for the given substrate while reacting with HBr . Concept introduction: Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond ( alkene ). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule. Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene. To draw: Intermediate for the given substrate in hydro halogenation reaction.

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Answer 1

Question

Chapter 9.3, Problem 4ATS

(a)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(b)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(c)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(d)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

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1. Base on this experimental results, how do you know that the product which you are turning in is methyl 3-nitrobenzoate(meta substituted product ) rather than either of the other two products? 2. What observation suggests that at least a small amount of one or both of the other two isomers are in the mother liquor?

Explain Huckel's rule.

Answer 2

Question

Chapter 9.3, Problem 4ATS

(a)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(b)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(c)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(d)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

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Answer 3

Question

Chapter 9.3, Problem 4ATS

(a)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(b)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(c)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(d)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

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Answer 4

Question

Chapter 9.3, Problem 4ATS

(a)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(b)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(c)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(d)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

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Answer 5

Chapter 9.3, Problem 4ATS

(a)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(b)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(c)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

(d)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

Answer 6

Chapter 9.3, Problem 4ATS

(a)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

Answer 7

Chapter 9.3, Problem 4ATS

(a)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

Answer 8

(b)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

Answer 9

(b)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

Answer 10

(c)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

Answer 11

(c)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

Answer 12

(d)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

Answer 13

(d)

Interpretation Introduction

Interpretation:

Intermediate carbocation should be drawn for the given substrate while reacting with HBr .

Concept introduction:

Hydro halogenation reaction: In hydro halogenation reaction hydrogen halide added across the unsaturated bond (alkene). In this addition reaction chloride ion added to the most substituted carbon position of the alkene, which follows the Markovnikov’s rule.

Markovnikov’s rule: In addition reactions negatively addendum goes to most substituted carbon position in alkene.

To draw: Intermediate for the given substrate in hydro halogenation reaction.

Answer 14

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Answer 16

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Answer 17

Ch. 9.3 - Prob. 3PTS Ch. 9.3 - Prob. 4ATS Ch. 9.3 - Prob. 5ATS Ch. 9.3 - Prob. 2LTS Ch. 9.3 - Prob. 7PTS Ch. 9.3 - Prob. 8ATS Ch. 9.3 - Prob. 9ATS Ch. 9.4 - Prob. 10CC Ch. 9.4 - Prob. 11CC Ch. 9.4 - Prob. 3LTS

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Chapter 9 Solutions