a) Interpretation: The product formed with its stereochemistry, when 1,2-dimethylcyclohexene reacts with Br 2 is to be given. The mechanism of its formation also is to be given. Concept introduction: The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans- product. To give: The product expected, along with its stereochemistry, when Br 2 is added to 1,2-dimethylcyclohexene.

Question

. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

Answer 1

Question

Chapter 8.SE, Problem 26MP

Interpretation Introduction

a)

Interpretation:

The product formed with its stereochemistry, when 1,2-dimethylcyclohexene reacts with Br₂ is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Br₂ is added to 1,2-dimethylcyclohexene.

Interpretation Introduction

b)

Interpretation:

The product obtained with its stereochemistry, in the reaction shown, is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond, one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to styrene (vinyl benzene).

Interpretation Introduction

c)

Interpretation:

The product obtained with its stereochemistry in the reaction shown is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to 2-butene.

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. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage

Which carbocation is more stable?

Are the products of the given reaction correct? Why or why not?

Answer 2

Question

Chapter 8.SE, Problem 26MP

Interpretation Introduction

a)

Interpretation:

The product formed with its stereochemistry, when 1,2-dimethylcyclohexene reacts with Br₂ is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Br₂ is added to 1,2-dimethylcyclohexene.

Interpretation Introduction

b)

Interpretation:

The product obtained with its stereochemistry, in the reaction shown, is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond, one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to styrene (vinyl benzene).

Interpretation Introduction

c)

Interpretation:

The product obtained with its stereochemistry in the reaction shown is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to 2-butene.

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Answer 3

Question

Chapter 8.SE, Problem 26MP

Interpretation Introduction

a)

Interpretation:

The product formed with its stereochemistry, when 1,2-dimethylcyclohexene reacts with Br₂ is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Br₂ is added to 1,2-dimethylcyclohexene.

Interpretation Introduction

b)

Interpretation:

The product obtained with its stereochemistry, in the reaction shown, is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond, one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to styrene (vinyl benzene).

Interpretation Introduction

c)

Interpretation:

The product obtained with its stereochemistry in the reaction shown is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to 2-butene.

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Answer 4

Question

Chapter 8.SE, Problem 26MP

Interpretation Introduction

a)

Interpretation:

The product formed with its stereochemistry, when 1,2-dimethylcyclohexene reacts with Br₂ is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Br₂ is added to 1,2-dimethylcyclohexene.

Interpretation Introduction

b)

Interpretation:

The product obtained with its stereochemistry, in the reaction shown, is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond, one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to styrene (vinyl benzene).

Interpretation Introduction

c)

Interpretation:

The product obtained with its stereochemistry in the reaction shown is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to 2-butene.

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Answer 5

Chapter 8.SE, Problem 26MP

Interpretation Introduction

a)

Interpretation:

The product formed with its stereochemistry, when 1,2-dimethylcyclohexene reacts with Br₂ is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Br₂ is added to 1,2-dimethylcyclohexene.

Interpretation Introduction

b)

Interpretation:

The product obtained with its stereochemistry, in the reaction shown, is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond, one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to styrene (vinyl benzene).

Interpretation Introduction

c)

Interpretation:

The product obtained with its stereochemistry in the reaction shown is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to 2-butene.

Answer 6

Chapter 8.SE, Problem 26MP

Interpretation Introduction

a)

Interpretation:

The product formed with its stereochemistry, when 1,2-dimethylcyclohexene reacts with Br₂ is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Br₂ is added to 1,2-dimethylcyclohexene.

Answer 7

Chapter 8.SE, Problem 26MP

Interpretation Introduction

a)

Interpretation:

The product formed with its stereochemistry, when 1,2-dimethylcyclohexene reacts with Br₂ is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Br₂ is added to 1,2-dimethylcyclohexene.

Answer 8

Interpretation Introduction

b)

Interpretation:

The product obtained with its stereochemistry, in the reaction shown, is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond, one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to styrene (vinyl benzene).

Answer 9

Interpretation Introduction

b)

Interpretation:

The product obtained with its stereochemistry, in the reaction shown, is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond, one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to styrene (vinyl benzene).

Answer 10

Interpretation Introduction

c)

Interpretation:

The product obtained with its stereochemistry in the reaction shown is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to 2-butene.

Answer 11

Interpretation Introduction

c)

Interpretation:

The product obtained with its stereochemistry in the reaction shown is to be given. The mechanism of its formation also is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step, the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The large halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield a trans-product.

To give:

The product expected, along with its stereochemistry, when Cl₂ is added to 2-butene.

Answer 12

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Answer 23

Ch. 8.1 - Prob. 1P Ch. 8.1 - How many alkene products, including E,Z isomers,...Ch. 8.2 - Prob. 3P Ch. 8.2 - Addition of HCl to 1, 2-dimethylcyclohexene yields...Ch. 8.3 - Prob. 5P Ch. 8.3 - Prob. 6P Ch. 8.4 - Prob. 7P Ch. 8.4 - From what alkenes might the following alcohols...Ch. 8.5 - Prob. 9P Ch. 8.5 - What alkenes might be used to prepare the...

Solution Summary: The author explains the product formed with its stereochemistry when 1,2-dimethylcyclohexene reacts with Br2 and the mechanism of its formation.

Chapter 8 Solutions