Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 9, Problem 54P

(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 (pKa = 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 1o or 2o alkyl halides (Cl, Br or I) which can produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene (acetylene) H-CC-H can be susbtituted providing access to monosubstituted (H-CC-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-CC-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 (pKa = 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 1o or 2o alkyl halides (Cl, Br or I) which can produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene (acetylene) H-CC-H can be susbtituted providing access to monosubstituted (H-CC-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-CC-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 (pKa = 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 1o or 2o alkyl halides (Cl, Br or I) which can produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene (acetylene) H-CC-H can be susbtituted providing access to monosubstituted (H-CC-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-CC-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 (pKa = 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 1o or 2o alkyl halides (Cl, Br or I) which can produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

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

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

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