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Propose mechanisms for the following reactions. Does this

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 49SP Chapter 21

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 49SP

Problem 49SP

Propose mechanisms for the following reactions.

Does this reaction proceed with retention, inversion, or racemization of the asymmetric carbon atom?

Step-by-Step Solution:
Step 1 of 3

Solution  49SP

(a)

Acid chloride reacts with alcohol to from an ester. The reaction is shown below:

The mechanism of the reaction is shown below:

In step-I, alcohol acts as a nucleophile which attacks on the electrophilic carbonyl carbon to form tetrahedral intermediate.

In step-II, chlorine leaves with a pair of electrons to form protonated ester.

In the final step, deprotonation to form target product.

(b)

Esters undergo base promoted hydrolysis in presence of NaOH and water to form carboxylate ion and alcohol.

The mechanism of the reaction is shown below:

In step-1, hydroxide ion acts as a nucleophile which attacks on the electrophilic carbonyl carbon to form alkoxide ion.

In step-2, ethoxide ion leaves with pair of electrons to form benzoic acid and ethoxide ion.

In final step, ethoxide ion is strong base which abstracts a proton from benzoic acid to form benzoate and methanol.

(c)

Esters undergo acid catalyzed hydrolysis in presence of and water to form carboxylic acid and alcohol.

The mechanism of the reaction is shown below:

In step-I, carbonyl oxygen abstracts proton from acid to form protonated ester.

In step-2, water molecule acts as nucleophile which attacks on the electrophilic carbonyl carbon to form bond between carbon and oxygen.

In step-3, oxygen atom is deprotonated by oxygen atom of ethoxide ion.

In step-4, ethoxide ion leaves with a pair of electrons to form protonated benzoic acid and ethanol followed by deprotonation to form benzoic acid and ethanol.

(d)

Cyclic ester undergo base-catalyzed trans esterification with ethanol to form (1S,3R)-ethyl 3-hydroxycyclopentanecarboxylate.

The top view of the given reactant is shown below:

aThe mechanism of the reaction is shown below:

In step-1, ethoxide ion attacks on the electrophilic carbonyl carbon to form bond between oxygen and carbon.

In step-2, oxygen atom leaves with pair of electrons to form alkoxide ion.

In the final step, alkoxide ion abstracts a proton from ethanol to from target product.

(e)

Amines react with aldehydes in presence of an acid to form imines. The reaction is shown below:

The mechanism of the reaction is shown below:

In step1, carbonyl oxygen abstracts proton from acid to form protonated aldehyde.

In step-2, lone pair electrons of amine attacks on the electrophilic carbonyl carbon to form bond between nitrogen and carbon.

Water molecule leaves with a pair of electrons followed by pushing of lone pair electrons from nitrogen to from protonated imine.

In final step, protonation imine undergo deprotonation to form imine.

(f)

Esters react with amine to form an amide. The reaction is shown below:

The mechanism of the reaction is shown below:

In step-1, lone pair electrons of amine attacks on the electrophilic carbonyl carbon of ester to form bond between carbon and nitrogen.

In step-2, methoxide ion leaves with a pair of electrons to form protonated amide and methoxide ion.

In final step, methoxide ion is a strong base which abstracts a proton from protonated amide.

(g)

Alcohols react with acetic anhydride to form sec-butyl acetate. He reaction undergoes with retention of configuration.

The mechanism of the reaction is shown below:

In step-I, lone pair electrons of alcohol attacks on the electrophilic carbonyl carbon atom.

In step-2, acetate ion leaves with a pair of electrons to form protonated ester.

In final step, acetate ion abstracts proton protonated ester to form sec-butyl acetate with retention of configuration.

Step 2 of 3

Chapter 21, Problem 49SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Propose mechanisms for the following reactions. Does this