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 N a N H 2 ) to generate a carbanion. The acetylide carbanion is a good nucleophile and can undergo nucleophilic substitution reactions (usually S N 2) with 1 o or 2 o alkyl halides ( C l , B r o r I ) which have electrophilic to produce an internal alkyne. 3 o alkyl halides are more likely to undergo elimination. One or both of the terminal H atoms in ethylene H − C ≡ C − H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R − C ≡ C − R ' . The product is also an alkyne, The S N 2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S N 2 is a kind of nucleophilic substitution reaction mechanism.

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Answer 1

Question

Chapter 9, Problem 120P

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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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Synthesis

The following transformations represent either a reversible or irreversible reaction with a carbonyl. In the box above each reaction , specify whether the reaction is reversible "R" or irreversible "T".

Please include detailed explanations and work. Please write out answers and steps to make them easy to understand.

Answer 2

Question

Chapter 9, Problem 120P

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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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Answer 3

Question

Chapter 9, Problem 120P

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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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Answer 4

Question

Chapter 9, Problem 120P

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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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Answer 5

Chapter 9, Problem 120P

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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.

Answer 6

Chapter 9, Problem 120P

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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.

Answer 7

Chapter 9, Problem 120P

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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.

Answer 8

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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.

Answer 9

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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.

Answer 10

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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.

Answer 11

(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 S_N2) with 1^o or 2^o alkyl halides (Cl, Br or I ) which have electrophilic to produce an internal alkyne.

3^o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene H−C≡C−H can be substituted providing access to monosubstituted and symmetrical or unsymmetrical (R not equal to R') substituted alkynes R−C≡C−R' . 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.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 9.1 - Prob. 3P Ch. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.1 - Prob. 8P Ch. 9.2 - Prob. 9P Ch. 9.2 - Prob. 10P Ch. 9.2 - Prob. 11P Ch. 9.2 - Prob. 12P Ch. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 15P

Solution Summary: The author explains terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated using an appropriate base to generate a carbanion.

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Chapter 9 Solutions