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 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 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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2. The following transformations represent either a reversible or irreversible reaction with a carbonyl. In the box above each reaction arrow, specify whether the reaction is reversible "R" or irreversible "I". a. H. b. d. HO OH

4. Show how you would complete each synthesis below. Draw each intermediate and list the steps above and below the arrow. a. b.

a. Propose a mechanism for the following reaction.b. Explain why two products are formed.c. Explain why methanol substitutes for only one of the bromines.

Answer 2

Question

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 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 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 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 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 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 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 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 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 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 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 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. 9.2 - Prob. 8P Ch. 9.2 - Prob. 9P Ch. 9.2 - Prob. 10P Ch. 9.2 - Prob. 11P Ch. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 14P Ch. 9.2 - Prob. 16P

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