(a) Interpretation: Anticipating the isolation of the potentially aromatic hydrocarbon B , a group of chemists irradiated compound A with ultraviolet light. Compound C was obtained as a product instead of B . The reason for compound B might be expected to be unstable in spite of its cyclic array of 4n+2 π electrons is to be stated. Concept introduction: The stability of aromatic compounds is high due to their stabilization energy. In order to retain their aromaticity (resultant stabilization energy) aromatic compounds undergo substitution reaction more readily. Aromaticity in compounds is considered only the system having 4n+2 π electrons, planar, cyclic, and should have conjugated π-electrons.

Question

(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?(c) Draw resonance forms to show the charge distribution on the pyrrole structure.

Answer 1

Question

Chapter 28, Problem 28.53AP

Interpretation Introduction

(a)

Interpretation:

Anticipating the isolation of the potentially aromatic hydrocarbon B, a group of chemists irradiated compound A with ultraviolet light. Compound C was obtained as a product instead of B.

The reason for compound B might be expected to be unstable in spite of its cyclic array of 4n+2 π electrons is to be stated.

Concept introduction:

The stability of aromatic compounds is high due to their stabilization energy. In order to retain their aromaticity (resultant stabilization energy) aromatic compounds undergo substitution reaction more readily. Aromaticity in compounds is considered only the system having 4n+2 π electrons, planar, cyclic, and should have conjugated π-electrons.

Interpretation Introduction

(b)

Interpretation:

The formation of compound B is allowed by the pericyclic selection rules is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The word ‘pericyclic’ means around the cycle. Notably, the pericyclic reactions are classified as electrocyclic, cycloaddition and sigmatropic reactions based on the activation of reaction, the number of electrons involved and the stereochemistry outcome of the reactions. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Interpretation Introduction

(c)

Interpretation:

The formation of the observed product C is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

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(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?(c) Draw resonance forms to show the charge distribution on the pyrrole structure.

Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.

2) The Diels-Alder reaction, developed by German chemists Otto Diels and Kurt Alder (who received the Nobel Prize in 1950 for their discovery), has great synthetic importance due to the possibility of forming an unsaturated six-membered cycle without involving intermediates ionic. About the reaction, answer: (a) Indicate the reagents necessary for the synthesis of the following compounds, indicating who is the diene and who is the dienophile.

Answer 2

Question

Chapter 28, Problem 28.53AP

Interpretation Introduction

(a)

Interpretation:

Anticipating the isolation of the potentially aromatic hydrocarbon B, a group of chemists irradiated compound A with ultraviolet light. Compound C was obtained as a product instead of B.

The reason for compound B might be expected to be unstable in spite of its cyclic array of 4n+2 π electrons is to be stated.

Concept introduction:

The stability of aromatic compounds is high due to their stabilization energy. In order to retain their aromaticity (resultant stabilization energy) aromatic compounds undergo substitution reaction more readily. Aromaticity in compounds is considered only the system having 4n+2 π electrons, planar, cyclic, and should have conjugated π-electrons.

Interpretation Introduction

(b)

Interpretation:

The formation of compound B is allowed by the pericyclic selection rules is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The word ‘pericyclic’ means around the cycle. Notably, the pericyclic reactions are classified as electrocyclic, cycloaddition and sigmatropic reactions based on the activation of reaction, the number of electrons involved and the stereochemistry outcome of the reactions. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Interpretation Introduction

(c)

Interpretation:

The formation of the observed product C is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

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Answer 3

Question

Chapter 28, Problem 28.53AP

Interpretation Introduction

(a)

Interpretation:

Anticipating the isolation of the potentially aromatic hydrocarbon B, a group of chemists irradiated compound A with ultraviolet light. Compound C was obtained as a product instead of B.

The reason for compound B might be expected to be unstable in spite of its cyclic array of 4n+2 π electrons is to be stated.

Concept introduction:

The stability of aromatic compounds is high due to their stabilization energy. In order to retain their aromaticity (resultant stabilization energy) aromatic compounds undergo substitution reaction more readily. Aromaticity in compounds is considered only the system having 4n+2 π electrons, planar, cyclic, and should have conjugated π-electrons.

Interpretation Introduction

(b)

Interpretation:

The formation of compound B is allowed by the pericyclic selection rules is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The word ‘pericyclic’ means around the cycle. Notably, the pericyclic reactions are classified as electrocyclic, cycloaddition and sigmatropic reactions based on the activation of reaction, the number of electrons involved and the stereochemistry outcome of the reactions. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Interpretation Introduction

(c)

Interpretation:

The formation of the observed product C is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

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Answer 4

Question

Chapter 28, Problem 28.53AP

Interpretation Introduction

(a)

Interpretation:

Anticipating the isolation of the potentially aromatic hydrocarbon B, a group of chemists irradiated compound A with ultraviolet light. Compound C was obtained as a product instead of B.

The reason for compound B might be expected to be unstable in spite of its cyclic array of 4n+2 π electrons is to be stated.

Concept introduction:

The stability of aromatic compounds is high due to their stabilization energy. In order to retain their aromaticity (resultant stabilization energy) aromatic compounds undergo substitution reaction more readily. Aromaticity in compounds is considered only the system having 4n+2 π electrons, planar, cyclic, and should have conjugated π-electrons.

Interpretation Introduction

(b)

Interpretation:

The formation of compound B is allowed by the pericyclic selection rules is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The word ‘pericyclic’ means around the cycle. Notably, the pericyclic reactions are classified as electrocyclic, cycloaddition and sigmatropic reactions based on the activation of reaction, the number of electrons involved and the stereochemistry outcome of the reactions. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Interpretation Introduction

(c)

Interpretation:

The formation of the observed product C is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

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Answer 5

Chapter 28, Problem 28.53AP

Interpretation Introduction

(a)

Interpretation:

Anticipating the isolation of the potentially aromatic hydrocarbon B, a group of chemists irradiated compound A with ultraviolet light. Compound C was obtained as a product instead of B.

The reason for compound B might be expected to be unstable in spite of its cyclic array of 4n+2 π electrons is to be stated.

Concept introduction:

The stability of aromatic compounds is high due to their stabilization energy. In order to retain their aromaticity (resultant stabilization energy) aromatic compounds undergo substitution reaction more readily. Aromaticity in compounds is considered only the system having 4n+2 π electrons, planar, cyclic, and should have conjugated π-electrons.

Interpretation Introduction

(b)

Interpretation:

The formation of compound B is allowed by the pericyclic selection rules is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The word ‘pericyclic’ means around the cycle. Notably, the pericyclic reactions are classified as electrocyclic, cycloaddition and sigmatropic reactions based on the activation of reaction, the number of electrons involved and the stereochemistry outcome of the reactions. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Interpretation Introduction

(c)

Interpretation:

The formation of the observed product C is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Answer 6

Chapter 28, Problem 28.53AP

Interpretation Introduction

(a)

Interpretation:

Anticipating the isolation of the potentially aromatic hydrocarbon B, a group of chemists irradiated compound A with ultraviolet light. Compound C was obtained as a product instead of B.

The reason for compound B might be expected to be unstable in spite of its cyclic array of 4n+2 π electrons is to be stated.

Concept introduction:

The stability of aromatic compounds is high due to their stabilization energy. In order to retain their aromaticity (resultant stabilization energy) aromatic compounds undergo substitution reaction more readily. Aromaticity in compounds is considered only the system having 4n+2 π electrons, planar, cyclic, and should have conjugated π-electrons.

Answer 7

Chapter 28, Problem 28.53AP

Interpretation Introduction

(a)

Interpretation:

Anticipating the isolation of the potentially aromatic hydrocarbon B, a group of chemists irradiated compound A with ultraviolet light. Compound C was obtained as a product instead of B.

The reason for compound B might be expected to be unstable in spite of its cyclic array of 4n+2 π electrons is to be stated.

Concept introduction:

The stability of aromatic compounds is high due to their stabilization energy. In order to retain their aromaticity (resultant stabilization energy) aromatic compounds undergo substitution reaction more readily. Aromaticity in compounds is considered only the system having 4n+2 π electrons, planar, cyclic, and should have conjugated π-electrons.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The formation of compound B is allowed by the pericyclic selection rules is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The word ‘pericyclic’ means around the cycle. Notably, the pericyclic reactions are classified as electrocyclic, cycloaddition and sigmatropic reactions based on the activation of reaction, the number of electrons involved and the stereochemistry outcome of the reactions. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The formation of compound B is allowed by the pericyclic selection rules is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The word ‘pericyclic’ means around the cycle. Notably, the pericyclic reactions are classified as electrocyclic, cycloaddition and sigmatropic reactions based on the activation of reaction, the number of electrons involved and the stereochemistry outcome of the reactions. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The formation of the observed product C is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The formation of the observed product C is to be explained.

Concept introduction:

Pericyclic reactions deal with electrons shift in a concerted manner. Moreover, in these reactions the breaking of reactant bonds and the formation of product bonds are formed at the same time.i.e., without the formation of intermediates. The selection rules of pericyclic reaction deal mostly on the rates of reaction and does not tell anything about position of equilibrium and equilibrium constant values.

Answer 12

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Answer 23

Ch. 28 - Prob. 28.1P Ch. 28 - Prob. 28.2P Ch. 28 - Prob. 28.3P Ch. 28 - Prob. 28.4P Ch. 28 - Prob. 28.5P Ch. 28 - Prob. 28.6P Ch. 28 - Prob. 28.7P Ch. 28 - Prob. 28.8P Ch. 28 - Prob. 28.9P Ch. 28 - Prob. 28.10P

Solution Summary: The author explains that the formation of compound B is allowed by the pericyclic selection rules.

Chapter 28 Solutions