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(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
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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 (
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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 (
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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 (
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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
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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)
- What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 3 2. n-BuLi • Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Click and drag to start drawing a structure.arrow_forwardIdentify the missing organic reactants in the following reaction: X + Y H+ two steps Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H2O) are not shown. In the drawing area below, draw the skeletal ("line") structures of the missing organic reactants X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. Х :arrow_forwardDraw the mechanism of friedel-crafts acylation using acetyl chloride of m-Xylenearrow_forward
- Don't used hand raiting and don't used Ai solution and correct answerarrow_forwardH R Part: 1/2 :CI: is a/an electrophile Part 2 of 2 Draw the skeletal structure of the product(s) for the Lewis acid-base reaction. Include lone pairs and formal charges (if applicable) on the structures. 4-7: H ö- H Skip Part Check X :C1: $ % L Fi Click and drag to start drawing a structure. MacBook Pro & ㅁ x G 0: P Add or increase positive formal cha Save For Later Submit ©2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Centearrow_forwardDraw the friedel-crafts acylation mechanism of m-Xylenearrow_forward
- Don't used hand raiting and don't used Ai solutionarrow_forward1. Base on this experimental results, how do you know that the product which you are turning in is methyl 3-nitrobenzoate(meta substituted product ) rather than either of the other two products? 2. What observation suggests that at least a small amount of one or both of the other two isomers are in the mother liquor?arrow_forwardExplain Huckel's rule.arrow_forward
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