
(a)
Interpretation:
The complete, detailed mechanism of a given reaction in mildly acidic medium is to be drawn and major organic product is to be predicted.
Concept introduction:
When a small amount of a strong acid is added to

Answer to Problem 18.57P
The complete, detailed mechanism of a given reaction in the acidic medium is shown below and an acetal is a major product.
Explanation of Solution
The given reaction is
This is an imine formation reaction in which the reaction is catalyzed under mildly acidic condition and the excess ammonia acts as the nucleophile. Ammonia attacks the
First three steps are the nucleophilic addition reactions on the ketone. In the first step, nucleophile
In the next step, deprotonation takes place by ammonia
Next, negativively charged oxygen ion abstracts the proton from the ammonium ion.
The lone pairs on
The
Ammonia nucleophile abstracts the proton from the amino group and forms imine as the product.
The complete, detailed mechanism of the given reaction under mildly acidic medium is shown below and an imine is the major product.
The complete, detailed mechanism of the given reaction under mildly acidic medium and excess ammonia is drawn.
(b)
Interpretation:
The complete, detailed mechanism of a given reaction in the acidic medium is to be drawn and major organic product is to be predicted.
Concept introduction:
When a small amount of a strong acid is added to ketone or an aldehyde, the uncharged nucleophile ammonia (

Answer to Problem 18.57P
The complete, detailed mechanism of the given reaction in the acidic medium is shown below and an acetal is the major product.
Explanation of Solution
The given reaction is
This is an imine formation reaction in which the reaction is catalyzed under mildly acidic condition and excess methylamine acts as the nucleophile.
First three steps are nucleophilic addition reactions on ketone. In the first step, nucleophile
In the next step, deprotonation takes place by the ammonia
Next, negativively charged oxygen ion abstracts the proton from methylamino ion.
The lone pairs on
The
The complete, detailed mechanism of the given reaction under mildly acidic medium is shown below and an imine is the major product.
The complete, detailed mechanism of the given reaction under mildly acidic medium and excess methylamine is drawn.
(c)
Interpretation:
The complete, detailed mechanism of a given reaction under acidic medium is to be drawn and major organic product is to be predicted.
Concept introduction:
When a small amount of a strong acid is added to ketone or an aldehyde, the uncharged nucleophile ammonia (

Answer to Problem 18.57P
The complete, detailed mechanism of the given reaction in the acidic medium is shown below and an ketone is the major product.
Explanation of Solution
The given reaction is
This is an imine hydrolysis reaction under strongly acidic condition to produce ketone as the major product.
In the first step, the
Next, water nucleophile attacks the activated electrophilic carbon by nucleophilic addition reaction.
In the next step, deprotonation takes place by the nucleophile produced
The lone pairs on
The
The nucleophile water abstracts the proton in the resonance stabilized carbocation and produces ketone as the major product.
The complete, detailed mechanism of the given reaction under strongly acidic medium is shown below and ketone is the major product.
The complete, detailed mechanism of the given reaction under strongly acidic medium and excess water is drawn.
(d)
Interpretation:
The complete, detailed mechanism of the given reaction in the mildly acidic medium is to be drawn and major organic product is to be predicted.
Concept introduction:
When a small amount of a strong acid is added to ketone or an aldehyde, the uncharged nucleophile ammonia (

Answer to Problem 18.57P
The complete, detailed mechanism of the given reaction in mildly acidic medium is shown below and enamine is the major product.
Explanation of Solution
The given reaction is
This is an enamine formation reaction in which the reaction is catalyzed under mildly acidic conditions, and the secondary
First three steps are nucleophilic addition reactions on ketone. In the first step, nucleophile
In the next step, deprotonation takes place by
Next, negatively charged oxygen ion abstracts the proton from dimethylamino ion.
The lone pairs on
The
The complete, detailed mechanism of the given reaction in mildly acidic medium is shown below and enamine is the major product.
The complete, detailed mechanism of the given reaction under acidic medium and excess alcohol is drawn.
(e)
Interpretation:
The complete, detailed mechanism of a given reaction under strongly acidic medium is to be drawn and major organic product is to be predicted.
Concept introduction:
When a small amount of a strong acid is added to ketone or an aldehyde, the uncharged nucleophile

Answer to Problem 18.57P
The complete, detailed mechanism of the given reaction under strongly acidic medium is shown below and ketone is the major product.
Explanation of Solution
The given reaction is
This is an enamine hydrolysis reaction under strongly acidic condition to produce ketone as the major product.
In the first step,
Next, water nucleophile attacks the activated electrophilic carbon by nucleophilic addition reaction.
In the next step, deprotonation takes place by the nucleophile produced
The lone pairs on
The nucleophile water abstracts the proton in the resonance stabilized carbocation and produces ketone as the major product.
The complete, detailed mechanism of the given reaction in the acidic medium is shown below and an acetal is the major product.
The complete, detailed mechanism of the given reaction under strongly acidic medium and excess water is drawn.
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Chapter 18 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
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