
Concept explainers
(a)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with the lithium enolate of acetone followed by
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of acetone followed by
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of acetone followed by
Figure 1
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
Lithium enolate of acetone attacks on the isobutyraldehyde from the carbon side and adds on the molecule. The acidic workup converts the oxide ion generated into alcohol group.
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of acetone followed by
(b)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with the lithium enolate of ethyl
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of ethyl
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of ethyl
Figure 2
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
Lithium enolate of
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of ethyl
(c)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with ethyl
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with ethyl
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with ethyl
Figure 3
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
The zinc metal converts the ethyl
The enolate ion generated attacks on the isobutyraldehyde from the carbon side and adds on the molecule. The acidic workup converts the oxide ion generated into alcohol group.
This reaction is a name reaction known as Reformatsky reaction.
The principal organic product obtained when isobutyraldehyde reacts with ethyl
(d)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with diethyl malonate and a secondary
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with diethyl malonate and a secondary amine
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with diethyl malonate and a secondary amine
Figure 4
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
Malonic ester is converted into the enolate ion by the secondary amine taken as the catalyst. The secondary amine pyridine taken here is basic in nature and takes up the acidic proton of the malonic ester.
The enolate ion generated attacks on the isobutyraldehyde from the carbon side and adds on the molecule. The acidic workup converts the oxide ion generated into alcohol group.
This reaction is a name reaction known as Knoevenagal reaction.
The principal organic product obtained when isobutyraldehyde reacts with diethyl malonate and a secondary amine
(e)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with ethyl acetoacetate and a secondary amine
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with ethyl acetoacetate and a secondary amine
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with ethyl acetoacetate and a secondary amine
Figure 5
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
Ethyl acetoacetate is converted into the enolate ion by the secondary amine taken as the catalyst. The secondary amine pyridine taken here is basic in nature and takes up the acidic proton of the malonic ester.
The enolate ion generated attacks on the isobutyraldehyde from the carbon side and adds on the molecule. The acidic workup converts the oxide ion generated into alcohol group.
This reaction is a name reaction known as Knoevenagal reaction.
The principal organic product obtained when isobutyraldehyde reacts with ethyl acetoacetate and a secondary amine
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Chapter 22 Solutions
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