EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
7th Edition
ISBN: 9780133556186
Author: Bruice
Publisher: VST
bartleby

Concept explainers

Question
Book Icon
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.

Blurred answer
Students have asked these similar questions
Don't used Ai solution
this is an organic chemistry question please answer accordindly!! please post the solution draw the figures and post, answer the question in a very simple and straight forward manner thanks!!!!! please answer EACH part till the end and dont just provide wordy explanations wherever asked for structures or diagrams, please draw them on a paper and post clearly!! answer the full question with all details EACH PART CLEARLY please thanks!! im reposting this kindly solve all parts and draw it not just word explanations!!
Please correct answer and don't used hand raiting

Chapter 9 Solutions

EBK ORGANIC CHEMISTRY

Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY