a) Interpretation: The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed. Concept introduction: The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution. To show: The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Question

Predict the product of the following reaction. Include stereochemistry if necessary.

Answer 1

Question

Chapter 9.8, Problem 10P

Interpretation Introduction

a)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

b)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of a hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

c)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

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Predict the product of the following reaction. Include stereochemistry if necessary.

Diphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?

Provide the major substitution product for the following reactions.

Answer 2

Question

Chapter 9.8, Problem 10P

Interpretation Introduction

a)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

b)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of a hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

c)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

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Answer 3

Question

Chapter 9.8, Problem 10P

Interpretation Introduction

a)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

b)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of a hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

c)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

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Answer 4

Question

Chapter 9.8, Problem 10P

Interpretation Introduction

a)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

b)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of a hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

c)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

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Answer 5

Chapter 9.8, Problem 10P

Interpretation Introduction

a)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

b)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of a hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Interpretation Introduction

c)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Answer 6

Chapter 9.8, Problem 10P

Interpretation Introduction

a)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Answer 7

Chapter 9.8, Problem 10P

Interpretation Introduction

a)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Answer 8

Interpretation Introduction

b)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of a hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Answer 9

Interpretation Introduction

b)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of a hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Answer 10

Interpretation Introduction

c)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Answer 11

Interpretation Introduction

c)

Interpretation:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained are to be shown. If two routes are possible both has to be listed.

Concept introduction:

The alkylation of alkynes is an efficient method for preparing higher alkanes. Acetylene upon alkylation gives a terminal alkyne while further alkylation of a terminal alkyne leads to the formation of an internal alkyne. The actylide anion, being nucleophilic in nature, displaces the halide ion when treated with alkyl halide and gets itself attached to the alkyl group to yield a terminal alkyne. Only primary alkyl halides can be used in the reaction because when secondary and tertiary alkyl halides are used elimination of hydrogen halide occurs instead of substitution.

To show:

The terminal alkyne and the alkyl halide from which the compound shown can be obtained. Further to list both routes if two routes are possible.

Answer 12

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Answer 13

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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 explains that the alkylation method is an efficient method for preparing higher alkanes. The actylide anion, being nucleophilic, displaces the halide ion

Chapter 9 Solutions