a) Interpretation: Assuming that halogens add to alkynes in the same manner as they add to alkenes , a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br 2 adds to 2-butyne is/are to be predicted. Concept introduction: Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product. To propose: A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br 2 adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Question

Draw the structural formula of the alkene that reacts with ozone followed by dimethyl sulfide to give product or set of products.

Answer 1

Question

Chapter 9.SE, Problem 18MP

Interpretation Introduction

a)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

b)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction, the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne assuming that chlorine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

c)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

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Draw the structural formula of the alkene that reacts with ozone followed by dimethyl sulfide to give product or set of products.

The rate law for addition of Br2Br2 to an alkene is first order in Br2Br2 and first order in the alkene. Does this information suggest that the mechanism of addition of Br2Br2 to an alkene proceeds in the same manner as for addition of HBr? Explain.

Provide structure(s) for the starting material(s), reagent(s) or the major organic product(s) of each of the following reactions.

Answer 2

Question

Chapter 9.SE, Problem 18MP

Interpretation Introduction

a)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

b)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction, the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne assuming that chlorine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

c)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

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Answer 3

Question

Chapter 9.SE, Problem 18MP

Interpretation Introduction

a)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

b)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction, the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne assuming that chlorine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

c)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

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Answer 4

Question

Chapter 9.SE, Problem 18MP

Interpretation Introduction

a)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

b)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction, the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne assuming that chlorine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

c)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

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Answer 5

Chapter 9.SE, Problem 18MP

Interpretation Introduction

a)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

b)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction, the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne assuming that chlorine adds to alkynes in the same manner as they add to alkenes.

Interpretation Introduction

c)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Answer 6

Chapter 9.SE, Problem 18MP

Interpretation Introduction

a)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Answer 7

Chapter 9.SE, Problem 18MP

Interpretation Introduction

a)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Answer 8

Interpretation Introduction

b)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction, the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne assuming that chlorine adds to alkynes in the same manner as they add to alkenes.

Answer 9

Interpretation Introduction

b)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction, the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Cl₂ adds to 1-phenylpropyne assuming that chlorine adds to alkynes in the same manner as they add to alkenes.

Answer 10

Interpretation Introduction

c)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Answer 11

Interpretation Introduction

c)

Interpretation:

Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne is/are to be predicted.

Concept introduction:

Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction the nucleophilic attack of the Ï€ electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.

To propose:

A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br₂ adds to 1-pentyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.

Answer 12

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Answer 23

Ch. 9.1 - Prob. 1P Ch. 9.1 - Prob. 2P Ch. 9.3 - What products would you expect from the following...Ch. 9.4 - Prob. 4P Ch. 9.4 - Prob. 5P Ch. 9.4 - Prob. 6P Ch. 9.4 - Prob. 7P Ch. 9.5 - Using any alkyne needed, how would you prepare the...Ch. 9.7 - The pKa of acetone, CH3COCH3, is 19.3. Which of...Ch. 9.8 - Prob. 10P

Solution Summary: The author proposes a mechanism and predicts the product(s) expected for the reaction in which two equivalents of Br 2 add to 2-butyne.

Chapter 9 Solutions