(a) Interpretation: Which isomers of C 10 H 14 with two fused six-membered rings will react with ethene in a Diels–Alder reaction and which will not is to be determined. Concept introduction: The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s -cis conformation. The Diels–Alder reactions cannot take place with the diene in the s -trans conformation. In s -cis conformation, the two ends of the π system point in nearly the same direction, and in s -trans conformation, the ends of the two reacting species are farther apart.

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Answer 1

Question

Chapter 24, Problem 24.31P

Interpretation Introduction

(a)

Interpretation:

Which isomers of C10H14 with two fused six-membered rings will react with ethene in a Diels–Alder reaction and which will not is to be determined.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Interpretation Introduction

(b)

Interpretation:

One more isomer of C10H14 with two fused six-membered rings that will react with ethene in a Diels–Alder reaction is to be drawn.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

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Answer 2

Question

Chapter 24, Problem 24.31P

Interpretation Introduction

(a)

Interpretation:

Which isomers of C10H14 with two fused six-membered rings will react with ethene in a Diels–Alder reaction and which will not is to be determined.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Interpretation Introduction

(b)

Interpretation:

One more isomer of C10H14 with two fused six-membered rings that will react with ethene in a Diels–Alder reaction is to be drawn.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

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Answer 3

Question

Chapter 24, Problem 24.31P

Interpretation Introduction

(a)

Interpretation:

Which isomers of C10H14 with two fused six-membered rings will react with ethene in a Diels–Alder reaction and which will not is to be determined.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Interpretation Introduction

(b)

Interpretation:

One more isomer of C10H14 with two fused six-membered rings that will react with ethene in a Diels–Alder reaction is to be drawn.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

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Answer 4

Question

Chapter 24, Problem 24.31P

Interpretation Introduction

(a)

Interpretation:

Which isomers of C10H14 with two fused six-membered rings will react with ethene in a Diels–Alder reaction and which will not is to be determined.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Interpretation Introduction

(b)

Interpretation:

One more isomer of C10H14 with two fused six-membered rings that will react with ethene in a Diels–Alder reaction is to be drawn.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

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Answer 5

Chapter 24, Problem 24.31P

Interpretation Introduction

(a)

Interpretation:

Which isomers of C10H14 with two fused six-membered rings will react with ethene in a Diels–Alder reaction and which will not is to be determined.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Interpretation Introduction

(b)

Interpretation:

One more isomer of C10H14 with two fused six-membered rings that will react with ethene in a Diels–Alder reaction is to be drawn.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Answer 6

Chapter 24, Problem 24.31P

Interpretation Introduction

(a)

Interpretation:

Which isomers of C10H14 with two fused six-membered rings will react with ethene in a Diels–Alder reaction and which will not is to be determined.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Answer 7

Chapter 24, Problem 24.31P

Interpretation Introduction

(a)

Interpretation:

Which isomers of C10H14 with two fused six-membered rings will react with ethene in a Diels–Alder reaction and which will not is to be determined.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Answer 8

Interpretation Introduction

(b)

Interpretation:

One more isomer of C10H14 with two fused six-membered rings that will react with ethene in a Diels–Alder reaction is to be drawn.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Answer 9

Interpretation Introduction

(b)

Interpretation:

One more isomer of C10H14 with two fused six-membered rings that will react with ethene in a Diels–Alder reaction is to be drawn.

Concept introduction:

The Diels-Alder reaction is the cycloaddition of diene and dienophile. The diene has a pair of conjugate double and contributes its 4π electrons. The dienophile has single double bond and contributes its 2π electrons. These six electrons must flow in a cyclic fashion. Thus, the reaction proceeds through a cyclic transition state, which makes it a pericyclic reaction. Therefore, the Diels-Alder reaction is called [4+2] cycloaddition. The two C=C bonds in diene must be conjugated and able to attain the s-cis conformation. The Diels–Alder reactions cannot take place with the diene in the s-trans conformation. In s-cis conformation, the two ends of the π system point in nearly the same direction, and in s-trans conformation, the ends of the two reacting species are farther apart.

Answer 10

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Answer 13

Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Prob. 24.3P Ch. 24 - Prob. 24.4P Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Prob. 24.7P Ch. 24 - Prob. 24.8P Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

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