Reaction between 1,3-Cyclopentadiene and cycloheptatrienone is suprafacial or antarafacial to give the product which is given below: Concept introduction: [6 + 4] Cycloaddition is a type of cycloaddition between a six-atom pi system and a four-atom pi system, leading to a ten-membered ring. It is a thermally allowed, higher-order cycloaddition process. Although most linear, acyclic trienes do not give [6 + 4] products selectively, cyclic trienes give high yields of [6 + 4] products in many cases. A suprafacial cycloaddition occurs when like phases of the p orbitals of both reactants are on the same side of the pie system, so that two bonding interactions result. An antarafacial cycloaddition occurs when one pie system must twist to align like phases of the p orbitals of the terminal carbons of the reactants.

Question

What product(s) would you expect from reaction of (S)-3-chloro-3methyloctane with acetic acid? Show the stereochemistry of both reactant and product.

Answer 1

Question

Chapter 30.6, Problem 6P

Interpretation Introduction

Interpretation:

Reaction between 1,3-Cyclopentadiene and cycloheptatrienone is suprafacial or antarafacial to give the product which is given below:

Concept introduction:

[6 + 4] Cycloaddition is a type of cycloaddition between a six-atom pi system and a four-atom pi system, leading to a ten-membered ring. It is a thermally allowed, higher-order cycloaddition process. Although most linear, acyclic trienes do not give [6 + 4] products selectively, cyclic trienes give high yields of [6 + 4] products in many cases.

A suprafacial cycloaddition occurs when like phases of the p orbitals of both reactants are on the same side of the pie system, so that two bonding interactions result.

An antarafacial cycloaddition occurs when one pie system must twist to align like phases of the p orbitals of the terminal carbons of the reactants.

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What product(s) would you expect from reaction of (S)-3-chloro-3methyloctane with acetic acid? Show the stereochemistry of both reactant and product.

A chiral ether of molecular formula C5H10O reacts with hot HI to give a product of molecular formula C5H10I2. Treatment of this compound with hot potassium tert-butoxide produces 1,3-pentadiene. determine the structure of the original ether?

What is the major product formed from reacting cyclohexene in aqueous Br2, followed by treatment with potassium tert-butoxide?

Answer 2

Question

Chapter 30.6, Problem 6P

Interpretation Introduction

Interpretation:

Reaction between 1,3-Cyclopentadiene and cycloheptatrienone is suprafacial or antarafacial to give the product which is given below:

Concept introduction:

[6 + 4] Cycloaddition is a type of cycloaddition between a six-atom pi system and a four-atom pi system, leading to a ten-membered ring. It is a thermally allowed, higher-order cycloaddition process. Although most linear, acyclic trienes do not give [6 + 4] products selectively, cyclic trienes give high yields of [6 + 4] products in many cases.

A suprafacial cycloaddition occurs when like phases of the p orbitals of both reactants are on the same side of the pie system, so that two bonding interactions result.

An antarafacial cycloaddition occurs when one pie system must twist to align like phases of the p orbitals of the terminal carbons of the reactants.

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Answer 3

Question

Chapter 30.6, Problem 6P

Interpretation Introduction

Interpretation:

Reaction between 1,3-Cyclopentadiene and cycloheptatrienone is suprafacial or antarafacial to give the product which is given below:

Concept introduction:

[6 + 4] Cycloaddition is a type of cycloaddition between a six-atom pi system and a four-atom pi system, leading to a ten-membered ring. It is a thermally allowed, higher-order cycloaddition process. Although most linear, acyclic trienes do not give [6 + 4] products selectively, cyclic trienes give high yields of [6 + 4] products in many cases.

A suprafacial cycloaddition occurs when like phases of the p orbitals of both reactants are on the same side of the pie system, so that two bonding interactions result.

An antarafacial cycloaddition occurs when one pie system must twist to align like phases of the p orbitals of the terminal carbons of the reactants.

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Answer 4

Question

Chapter 30.6, Problem 6P

Interpretation Introduction

Interpretation:

Reaction between 1,3-Cyclopentadiene and cycloheptatrienone is suprafacial or antarafacial to give the product which is given below:

Concept introduction:

[6 + 4] Cycloaddition is a type of cycloaddition between a six-atom pi system and a four-atom pi system, leading to a ten-membered ring. It is a thermally allowed, higher-order cycloaddition process. Although most linear, acyclic trienes do not give [6 + 4] products selectively, cyclic trienes give high yields of [6 + 4] products in many cases.

A suprafacial cycloaddition occurs when like phases of the p orbitals of both reactants are on the same side of the pie system, so that two bonding interactions result.

An antarafacial cycloaddition occurs when one pie system must twist to align like phases of the p orbitals of the terminal carbons of the reactants.

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Answer 5

Chapter 30.6, Problem 6P

Interpretation Introduction

Interpretation:

Reaction between 1,3-Cyclopentadiene and cycloheptatrienone is suprafacial or antarafacial to give the product which is given below:

Concept introduction:

[6 + 4] Cycloaddition is a type of cycloaddition between a six-atom pi system and a four-atom pi system, leading to a ten-membered ring. It is a thermally allowed, higher-order cycloaddition process. Although most linear, acyclic trienes do not give [6 + 4] products selectively, cyclic trienes give high yields of [6 + 4] products in many cases.

A suprafacial cycloaddition occurs when like phases of the p orbitals of both reactants are on the same side of the pie system, so that two bonding interactions result.

An antarafacial cycloaddition occurs when one pie system must twist to align like phases of the p orbitals of the terminal carbons of the reactants.

Answer 6

Chapter 30.6, Problem 6P

Interpretation Introduction

Interpretation:

Reaction between 1,3-Cyclopentadiene and cycloheptatrienone is suprafacial or antarafacial to give the product which is given below:

Concept introduction:

[6 + 4] Cycloaddition is a type of cycloaddition between a six-atom pi system and a four-atom pi system, leading to a ten-membered ring. It is a thermally allowed, higher-order cycloaddition process. Although most linear, acyclic trienes do not give [6 + 4] products selectively, cyclic trienes give high yields of [6 + 4] products in many cases.

A suprafacial cycloaddition occurs when like phases of the p orbitals of both reactants are on the same side of the pie system, so that two bonding interactions result.

An antarafacial cycloaddition occurs when one pie system must twist to align like phases of the p orbitals of the terminal carbons of the reactants.

Answer 7

Chapter 30.6, Problem 6P

Interpretation Introduction

Interpretation:

Reaction between 1,3-Cyclopentadiene and cycloheptatrienone is suprafacial or antarafacial to give the product which is given below:

Concept introduction:

[6 + 4] Cycloaddition is a type of cycloaddition between a six-atom pi system and a four-atom pi system, leading to a ten-membered ring. It is a thermally allowed, higher-order cycloaddition process. Although most linear, acyclic trienes do not give [6 + 4] products selectively, cyclic trienes give high yields of [6 + 4] products in many cases.

A suprafacial cycloaddition occurs when like phases of the p orbitals of both reactants are on the same side of the pie system, so that two bonding interactions result.

An antarafacial cycloaddition occurs when one pie system must twist to align like phases of the p orbitals of the terminal carbons of the reactants.

Answer 8

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Answer 19

Ch. 30.1 - Prob. 1P Ch. 30.3 - Prob. 2P Ch. 30.3 - Prob. 3P Ch. 30.4 - Prob. 4P Ch. 30.6 - What stereochemistry would you expect for the...Ch. 30.6 - Prob. 6P Ch. 30.7 - Prob. 7P Ch. 30.8 - Propose a mechanism to account for the fact that...Ch. 30.8 - When a 2, 6-disubstituted allyl phenyl ether is...Ch. 30.9 - Prob. 10P

Solution Summary: The author explains that 1,3-Cyclopentadiene reacts with cycloheptatrienone to give a suprafacial, or antarafacial reaction.

Chapter 30 Solutions