Using acetylene and any necessary organic and inorganic reagents, an efficient synthesis for the given alkynes is to be outlined. Concept Introduction: > Alkylation of acetylene takes place in two steps. Acetylene has two acidic protons, which can be abstracted by a strong base. > In the first step, the acetylene is treated with sodium amide to convert the acetylene to its conjugate base. > The acetylide ion reacts with an alkyl halide in the second step, forming a new carbon-carbon bond. The halide ion is displaced by a S N 2 type of reaction. > This sequence converts acetylene to its monosubstituted derivative, which is also a terminal alkyne. > Repeating this sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.

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Answer 1

Question

Chapter 9.6, Problem 5P

Interpretation Introduction

Interpretation:

Using acetylene and any necessary organic and inorganic reagents, an efficient synthesis for the given alkynes is to be outlined.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps. Acetylene has two acidic protons, which can be abstracted by a strong base.
>
In the first step, the acetylene is treated with sodium amide to convert the acetylene to its conjugate base.
>
The acetylide ion reacts with an alkyl halide in the second step, forming a new carbon-carbon bond. The halide ion is displaced by a SN2 type of reaction.
>
This sequence converts acetylene to its monosubstituted derivative, which is also a terminal alkyne.
>
Repeating this sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.

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Answer 2

Question

Chapter 9.6, Problem 5P

Interpretation Introduction

Interpretation:

Using acetylene and any necessary organic and inorganic reagents, an efficient synthesis for the given alkynes is to be outlined.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps. Acetylene has two acidic protons, which can be abstracted by a strong base.
>
In the first step, the acetylene is treated with sodium amide to convert the acetylene to its conjugate base.
>
The acetylide ion reacts with an alkyl halide in the second step, forming a new carbon-carbon bond. The halide ion is displaced by a SN2 type of reaction.
>
This sequence converts acetylene to its monosubstituted derivative, which is also a terminal alkyne.
>
Repeating this sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.

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Answer 3

Question

Chapter 9.6, Problem 5P

Interpretation Introduction

Interpretation:

Using acetylene and any necessary organic and inorganic reagents, an efficient synthesis for the given alkynes is to be outlined.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps. Acetylene has two acidic protons, which can be abstracted by a strong base.
>
In the first step, the acetylene is treated with sodium amide to convert the acetylene to its conjugate base.
>
The acetylide ion reacts with an alkyl halide in the second step, forming a new carbon-carbon bond. The halide ion is displaced by a SN2 type of reaction.
>
This sequence converts acetylene to its monosubstituted derivative, which is also a terminal alkyne.
>
Repeating this sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.

Expert Solution & Answer

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Answer 4

Question

Chapter 9.6, Problem 5P

Interpretation Introduction

Interpretation:

Using acetylene and any necessary organic and inorganic reagents, an efficient synthesis for the given alkynes is to be outlined.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps. Acetylene has two acidic protons, which can be abstracted by a strong base.
>
In the first step, the acetylene is treated with sodium amide to convert the acetylene to its conjugate base.
>
The acetylide ion reacts with an alkyl halide in the second step, forming a new carbon-carbon bond. The halide ion is displaced by a SN2 type of reaction.
>
This sequence converts acetylene to its monosubstituted derivative, which is also a terminal alkyne.
>
Repeating this sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.

Expert Solution & Answer

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Answer 5

Chapter 9.6, Problem 5P

Interpretation Introduction

Interpretation:

Using acetylene and any necessary organic and inorganic reagents, an efficient synthesis for the given alkynes is to be outlined.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps. Acetylene has two acidic protons, which can be abstracted by a strong base.
>
In the first step, the acetylene is treated with sodium amide to convert the acetylene to its conjugate base.
>
The acetylide ion reacts with an alkyl halide in the second step, forming a new carbon-carbon bond. The halide ion is displaced by a SN2 type of reaction.
>
This sequence converts acetylene to its monosubstituted derivative, which is also a terminal alkyne.
>
Repeating this sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.

Answer 6

Chapter 9.6, Problem 5P

Interpretation Introduction

Interpretation:

Using acetylene and any necessary organic and inorganic reagents, an efficient synthesis for the given alkynes is to be outlined.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps. Acetylene has two acidic protons, which can be abstracted by a strong base.
>
In the first step, the acetylene is treated with sodium amide to convert the acetylene to its conjugate base.
>
The acetylide ion reacts with an alkyl halide in the second step, forming a new carbon-carbon bond. The halide ion is displaced by a SN2 type of reaction.
>
This sequence converts acetylene to its monosubstituted derivative, which is also a terminal alkyne.
>
Repeating this sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.

Answer 7

Chapter 9.6, Problem 5P

Interpretation Introduction

Interpretation:

Using acetylene and any necessary organic and inorganic reagents, an efficient synthesis for the given alkynes is to be outlined.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps. Acetylene has two acidic protons, which can be abstracted by a strong base.
>
In the first step, the acetylene is treated with sodium amide to convert the acetylene to its conjugate base.
>
The acetylide ion reacts with an alkyl halide in the second step, forming a new carbon-carbon bond. The halide ion is displaced by a SN2 type of reaction.
>
This sequence converts acetylene to its monosubstituted derivative, which is also a terminal alkyne.
>
Repeating this sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 9.1 - Prob. 1P Ch. 9.2 - Prob. 2P Ch. 9.4 - How do bond distances and bond strengths change...Ch. 9.5 - Complete each of the following equations to show...Ch. 9.6 - Prob. 5P Ch. 9.6 - Which of the alkynes of molecular formula C5H8 can...Ch. 9.7 - Give the structures of three isomeric dibromides...Ch. 9.7 - Prob. 8P Ch. 9.9 - Write a series of equations showing how you could...Ch. 9.9 - Write a series of equations showing how to prepare...

Solution Summary: The author explains how an efficient synthesis for the given alkynes is outlined using acetylene and organic and inorganic reagents.

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