(a) Interpretation: The major product for the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it. Concept introduction: Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H 2 N - ( NaNH 2 ) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

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Answer 1

Question

Chapter 10, Problem 10.28P

Interpretation Introduction

(a)

Interpretation:

The major product for the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

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Will NBS (and heat or light) work for this reaction, or do we have to use Br2?

HAND DRAW

Predict the major products of the following organic reaction: Some important notes: Δ CN ? • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. ONO reaction. Click and drag to start drawing a structure.

Answer 2

Question

Chapter 10, Problem 10.28P

Interpretation Introduction

(a)

Interpretation:

The major product for the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

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Answer 3

Question

Chapter 10, Problem 10.28P

Interpretation Introduction

(a)

Interpretation:

The major product for the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

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Answer 4

Question

Chapter 10, Problem 10.28P

Interpretation Introduction

(a)

Interpretation:

The major product for the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

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Answer 5

Chapter 10, Problem 10.28P

Interpretation Introduction

(a)

Interpretation:

The major product for the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Answer 6

Chapter 10, Problem 10.28P

Interpretation Introduction

(a)

Interpretation:

The major product for the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Answer 7

Chapter 10, Problem 10.28P

Interpretation Introduction

(a)

Interpretation:

The major product for the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted, and the complete, detailed mechanism is to be drawn for it.

Concept introduction:

Terminal alkynes can be prepared from dihaloalkanes (1, 1-dihaloalkanes or 1, 2-dihaloalkanes) by treating them with a strong base via back to back E2 reaction. Three equivalents of the strong base H2N- (NaNH2) are used to convert the dihalides into a terminal alkyne. The first two equivalents bring about two separate E2 reactions removing an acidic hydrogen and a halogen atom each time. The third equivalent of the base deprotonates the acidic proton on the newly formed terminal alkyne. Acid workup is necessary whenever the reaction conditions are strongly basic. Acid workup replaces that proton.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 10 - Prob. 10.1P Ch. 10 - Prob. 10.2P Ch. 10 - Prob. 10.3P Ch. 10 - Prob. 10.4P Ch. 10 - Prob. 10.5P Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Prob. 10.10P

Solution Summary: The author explains how terminal alkynes can be prepared from dihaloalkanes by treating them with a strong base via back to back E2 reactions.

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Chapter 10 Solutions