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

AN IR spectrum, a 13 CMR spectrum, and a 1 HMR spectrum were obtained for an unknown structure with a molecular formula of C9H10. Draw the structure of this compound.

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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AN IR spectrum, a 13 CMR spectrum, and a 1 HMR spectrum were obtained for an unknown structure with a molecular formula of C9H10. Draw the structure of this compound.

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Q8: Draw the resonance structures for the following molecule. Show the curved arrows (how you derive each resonance structure). Circle the major resonance contributor.

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