
Concept explainers
(a)
Interpretation:
Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.
Concept Introduction:
Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce

Answer to Problem 22.22P
The given compound can be synthesized using aldol condensation in good yield. The starting materials are
Explanation of Solution
The given compound is shown below.
Figure 1
In the above preparation of the compound, the enolate is generated on the
Figure 2
The given compound can be synthesized by aldol condensation of
(b)
Interpretation:
Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.
Concept Introduction:
Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce

Answer to Problem 22.22P
The given compound can be synthesized using aldol condensation in good yield. The starting materials are benzaldehyde and
Explanation of Solution
The given compound is shown below.
Figure 3
In the preparation of the above compound, the enolate will be generated on the
The structures of the starting materials which are used to produce the given compound are shown below.
Figure 4
The given compound can be synthesized by aldol condensation of benzaldehyde and
(c)
Interpretation:
Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.
Concept Introduction:
Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce

Answer to Problem 22.22P
The given compound can be synthesized using aldol condensation but not in a good in good yield. The starting material is
Explanation of Solution
The given compound is shown below.
Figure 5
In the preparation of the above compound, intramolecular aldol condensation takes place. To form this compound enolate must be generated by aldehyde and it has to attack the carbonyl carbon of ketone which is not favorable condition. Favorable condition is that enolate should be generated on ketone which attacks the electrophilic carbon of the aldehyde. This is because the carbon of aldehyde is more acidic than the carbon of ketone. The structure of the starting material which is used to produce the given compound is shown below.
Figure 6
Therefore, the given compound cannot be synthesized by aldol condensation in a good yield.
This compound cannot be synthesized in a good yield by the aldol condensation.
(d)
Interpretation:
Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.
Concept Introduction:
Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce

Answer to Problem 22.22P
The given compound can be synthesized by aldol condensation in good yield. The starting material is
Explanation of Solution
The given compound is shown below.
Figure 7
The given compound, is prepared by the intramolecular aldol condensation of
Figure 8
The given compound can be synthesized by intramolecular aldol condensation of
(e)
Interpretation:
Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.
Concept Introduction:
Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce

Answer to Problem 22.22P
The given compound can be synthesized from aldol condensation in a good yield. The starting materials are:
Explanation of Solution
The given compound is shown below.
Figure 9
In the preparation of the given compound, the enolate will be generated on the
Figure 10
The given compound can be synthesized by aldol condensation of
(f)
Interpretation:
Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.
Concept Introduction:
Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce

Answer to Problem 22.22P
The given compound can be synthesized by aldol condensation in a good yield. The starting materials are
Explanation of Solution
The given compound is shown below.
Figure 11
In the preparation of the compound, the enolate is generated on the
Figure 12
The given compound can be synthesized by aldol condensation of benzaldehyde and acetone.
(g)
Interpretation:
Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.
Concept Introduction:
Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce

Answer to Problem 22.22P
The given compound can be synthesized by aldol condensation. The starting materials are trimethylacetone and acetaldehyde.
Explanation of Solution
The given compound is shown below.
Figure 13
In the preparation of the given compound, the enolate will be generated on the
Figure 14
The given compound can be synthesized by aldol condensation by trimethylacetone and acetaldehyde in a good yield.
(h)
Interpretation:
Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.
Concept Introduction:
Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce

Answer to Problem 22.22P
The given compound can be synthesized by aldol condensation in a good yield. The starting material is
Explanation of Solution
The given compound is shown below.
Figure 15
The enolate will be generated on the
Figure 16
The given compound can be synthesized by aldol condensation of
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Chapter 22 Solutions
EBK ORGANIC CHEMISTRY
- Q5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R Harrow_forwardCalculate the proton and carbon chemical shifts for this structurearrow_forwardA. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?arrow_forward
- A mixture of C7H12O2, C9H9OCl, biphenyl and acetone was put together in a gas chromatography tube. Please decide from the GC resutls which correspond to the peak for C7,C9 and biphenyl and explain the reasoning based on GC results. Eliminate unnecessary peaks from Gas Chromatography results.arrow_forwardIs the molecule chiral, meso, or achiral? CI .CH3 H₂C CIarrow_forwardPLEASE HELP ! URGENT!arrow_forward
- Identify priority of the substituents: CH3arrow_forwardHow many chiral carbons are in the molecule? OH F CI Brarrow_forwardA mixture of three compounds Phen-A, Acet-B and Rin-C was analyzed using TLC with 1:9 ethanol: hexane as the mobile phase. The TLC plate showed three spots of R, 0.1 and 0.2 and 0.3. Which of the three compounds (Phen-A; Acet-B or Rin-C) would have the highest (Blank 1), middle (Blank 2) and lowest (Blank 3) spot respectively? 0 CH: 0 CH, 0 H.C OH H.CN OH Acet-B Rin-C phen-A A A <arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
