The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction. Concept introduction: Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction. There are mainly three types of pericyclic reactions, 1) Electrocyclic reactions 2) Cycloaddition reactions 3) Sigmatropic reactions In an electrocyclic reaction “one new sigma- bond is formed or broken.” In a cycloaddition reaction “ two new sigma-bonds are formed or broken” In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

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Answer 1

Question

Chapter 28.1, Problem 1P

(a)

Interpretation Introduction

Interpretation:

The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(b)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(c)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(d)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

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Part II. xiao isolated a compound TAD (Ca H 10 N₂) from tobacco and obtained its IR spectrum. Xiao proposed a chemical structure shown below: % Transmittance 4000 3500 3000 2500 2000 Wavenumber (cm-1) 1500 1000 (a) Explain why her proposed structure is inconsistent with the IR spectrum obtained (b) TAD exists as a tautomer of the structure xiao proposed. Draw the structure and explain why it is more compatible with the obtained spectrum. (C) what is the possible source for the fairly intense signal at 1621cm1

AE>AE₁ (Y/N) AE=AE₁ (Y/N) AE

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Answer 2

Question

Chapter 28.1, Problem 1P

(a)

Interpretation Introduction

Interpretation:

The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(b)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(c)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(d)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

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Answer 3

Question

Chapter 28.1, Problem 1P

(a)

Interpretation Introduction

Interpretation:

The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(b)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(c)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(d)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Expert Solution & Answer

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Answer 4

Question

Chapter 28.1, Problem 1P

(a)

Interpretation Introduction

Interpretation:

The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(b)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(c)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(d)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Expert Solution & Answer

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Answer 5

Chapter 28.1, Problem 1P

(a)

Interpretation Introduction

Interpretation:

The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(b)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(c)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

(d)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Answer 6

Chapter 28.1, Problem 1P

(a)

Interpretation Introduction

Interpretation:

The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Answer 7

Chapter 28.1, Problem 1P

(a)

Interpretation Introduction

Interpretation:

The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Answer 8

(b)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Answer 9

(b)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Answer 10

(c)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Answer 11

(c)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Answer 12

(d)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Answer 13

(d)

Interpretation Introduction

Interpretation: The given reaction has to be identified as electro cyclic reaction, a cycloaddition reaction or a sigma tropic reaction.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or broken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

1) Electrocyclic reactions

2) Cycloaddition reactions

3) Sigmatropic reactions

In an electrocyclic reaction “one new sigma- bond is formed or broken.”

In a cycloaddition reaction “ two new sigma-bonds are formed or broken”

In a sigmatropic rearrangement reaction “ one new sigma-bond is formed as another breaks.”

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 28.1 - Prob. 1P Ch. 28.2 - Prob. 2P Ch. 28.2 - Prob. 3P Ch. 28.2 - Give a molecular orbital description for each of...Ch. 28.3 - Prob. 5P Ch. 28.3 - Prob. 6P Ch. 28.3 - Prob. 7P Ch. 28.3 - Prob. 8P Ch. 28.4 - Prob. 9P Ch. 28.4 - Prob. 11P

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Chapter 28 Solutions