Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
Question
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Chapter 9, Problem 60P

(a)

Interpretation Introduction

Interpretation:

The structure of products of given reaction should be drawn.

Concept Introduction:

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated using an appropriate base (typically  NaNH2 ) to generate a carbanion.

The acetylide carbanion is a good nucleophile and can undergo nucleophilic substitution reactions (usually SN2) with 1o or 2o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene HCCH can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes RCCR' . The product is also an alkyne,

The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.

(b)

Interpretation Introduction

Interpretation:

Two sets of reactants that could be used to synthesize a given compound should be given.

Concept Introduction:

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated using an appropriate base (typically  NaNH2 ) to generate a carbanion.

The acetylide carbanion is a good nucleophile and can undergo nucleophilic substitution reactions (usually SN2) with 1o or 2o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene HCCH can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes RCCR' . The product is also an alkyne,

The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.

(c)

Interpretation Introduction

Interpretation:

Two sets of reactants that could be used to synthesize a given compound should be given.

Concept Introduction:

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated using an appropriate base (typically  NaNH2 ) to generate a carbanion.

The acetylide carbanion is a good nucleophile and can undergo nucleophilic substitution reactions (usually SN2) with 1o or 2o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene HCCH can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes RCCR' . The product is also an alkyne,

The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.

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Chapter 9 Solutions

Organic Chemistry

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