Synthesis of n-pentane from 1-Bromo propane should be shown. Concept Introduction: Target molecule is nothing but the desired product. Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK a = 26) using an appropriate base 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 (Cl, Br or I) which can produce an internal alkyne. 3 o alkyl halides are more likely to undergo elimination. One or both of the terminal H atoms in ethylene (acetylene) H-C ≡ C-H can be susbtituted providing access to monosubstituted (H-C ≡ C-R) and symmetrical ( R = R' ) or unsymmetrical (R not equal to R') disubstituted alkynes R-C ≡ C-R' The product is also an alkyne; it can also undergo the other reactions.

Question

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Answer 1

Question

Chapter 9, Problem 106P

(a)

Interpretation Introduction

Interpretation:

Synthesis of n-pentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(b)

Interpretation Introduction

Interpretation:

Synthesis of 2-pentanone from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(c)

Interpretation Introduction

Interpretation:

Synthesis of Pentanal from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(d)

Interpretation Introduction

Interpretation:

Synthesis of 1, 2-epoxypentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

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Answer 2

Question

Chapter 9, Problem 106P

(a)

Interpretation Introduction

Interpretation:

Synthesis of n-pentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(b)

Interpretation Introduction

Interpretation:

Synthesis of 2-pentanone from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(c)

Interpretation Introduction

Interpretation:

Synthesis of Pentanal from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(d)

Interpretation Introduction

Interpretation:

Synthesis of 1, 2-epoxypentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

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Answer 3

Question

Chapter 9, Problem 106P

(a)

Interpretation Introduction

Interpretation:

Synthesis of n-pentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(b)

Interpretation Introduction

Interpretation:

Synthesis of 2-pentanone from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(c)

Interpretation Introduction

Interpretation:

Synthesis of Pentanal from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(d)

Interpretation Introduction

Interpretation:

Synthesis of 1, 2-epoxypentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

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Answer 4

Question

Chapter 9, Problem 106P

(a)

Interpretation Introduction

Interpretation:

Synthesis of n-pentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(b)

Interpretation Introduction

Interpretation:

Synthesis of 2-pentanone from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(c)

Interpretation Introduction

Interpretation:

Synthesis of Pentanal from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(d)

Interpretation Introduction

Interpretation:

Synthesis of 1, 2-epoxypentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

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Answer 5

Chapter 9, Problem 106P

(a)

Interpretation Introduction

Interpretation:

Synthesis of n-pentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(b)

Interpretation Introduction

Interpretation:

Synthesis of 2-pentanone from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(c)

Interpretation Introduction

Interpretation:

Synthesis of Pentanal from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

(d)

Interpretation Introduction

Interpretation:

Synthesis of 1, 2-epoxypentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

Answer 6

Chapter 9, Problem 106P

(a)

Interpretation Introduction

Interpretation:

Synthesis of n-pentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

Answer 7

Chapter 9, Problem 106P

(a)

Interpretation Introduction

Interpretation:

Synthesis of n-pentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

Answer 8

(b)

Interpretation Introduction

Interpretation:

Synthesis of 2-pentanone from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

Answer 9

(b)

Interpretation Introduction

Interpretation:

Synthesis of 2-pentanone from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

Answer 10

(c)

Interpretation Introduction

Interpretation:

Synthesis of Pentanal from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

Answer 11

(c)

Interpretation Introduction

Interpretation:

Synthesis of Pentanal from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

Answer 12

(d)

Interpretation Introduction

Interpretation:

Synthesis of 1, 2-epoxypentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

Answer 13

(d)

Interpretation Introduction

Interpretation:

Synthesis of 1, 2-epoxypentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pK_a = 26) using an appropriate base to generate a carbanion.

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

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

One or both of the terminal H atoms in ethylene (acetylene) H-C≡C-H can be susbtituted providing access to monosubstituted (H-C≡C-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-C≡C-R'

The product is also an alkyne; it can also undergo the other reactions.

Answer 14

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Answer 15

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Answer 16

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Answer 17

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 that 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