
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
Organic Chemistry
- 10. The most important reason why Br- is a better nucleophile than Cl-is ___. A. polarizability; B. size; C. solvation; D. basicity; E. polarity. Please include all steps. Thanks!arrow_forwardPredicting the qualitative acid-base properties of salts Consider the following data on some weak acids and weak bases: base acid Ка K₁₁ name formula name formula nitrous acid HNO2 4.5×10 4 pyridine CHEN 1.7 × 10 9 4 hydrofluoric acid HF 6.8 × 10 methylamine CH3NH2 | 4.4 × 10¯ Use this data to rank the following solutions in order of increasing pH. In other words, select a '1' next to the solution that will have the lowest pH, a '2' next to the solution that will have the next lowest pH, and so on. solution 0.1 M NaNO2 0.1 M KF pH choose one v choose one v 0.1 M C5H5NHBr 0.1 M CH3NH3CI choose one v ✓ choose one 1 (lowest) 2 ☑ 3 4 (highest) 000 18 Ararrow_forward4. The major product from treatment of 2-propanol with the Jonesreagent is ___.A. acetone; B. none of the other answers is correct C. propene; D.propanoic acid; E carbon dioxide. Please include all steps! Thank you!arrow_forward
- 7. All of the following compounds that are at the same oxidation levelare ___.u. methyl epoxide, v. propyne, w. propanal, x. propene,y. 2,2-dihydroxypropane, z. isopropanol?A. u,v,w,y; B. u,v,w; C. v,w,y,z; D. v, z; E. x,y,z Please include all steps. Thank you!arrow_forward9. Which one of the following substituents is the worst leaving group inan SN2 reaction? A. -NH2; B. -OH; C. –F; D. NH3; E. H2O Please include all steps. Thanks!arrow_forwardUsing the general properties of equilibrium constants At a certain temperature, the equilibrium constant K for the following reaction is 2.5 × 105: CO(g) + H2O(g) CO2(g) + H2(g) Use this information to complete the following table. Suppose a 7.0 L reaction vessel is filled with 1.7 mol of CO and 1.7 mol of H2O. What can you say about the composition of the mixture in the vessel at equilibrium? What is the equilibrium constant for the following reaction? Be sure your answer has the correct number of significant digits. CO2(9)+H2(g) CO(g)+H₂O(g) What is the equilibrium constant for the following reaction? Be sure your answer has the correct number of significant digits. 3 CO(g)+3H2O(g) = 3 CO2(g)+3H2(g) There will be very little CO and H2O. x10 There will be very little CO2 and H2. 000 Neither of the above is true. K = ☐ K = ☐ 18 Ararrow_forward
- 8. When ethane thiol is treated with hydrogen peroxide the product is___.A. ethane disulfide; B. diethyl sulfide; C. ethane sulfoxide; D. ethanesulfate; E. ethyl mercaptan. Please include all steps. Thanks!arrow_forward5. The major product of the three step reaction that takes place when 1-propanol is treated with strong acid is?A. dipropyl ether; B. propene; C. propanal; D. isopropyl propyl ether;E. 1-hexanol Please include all steps. Thank you!arrow_forward6. The formula of the product of the addition of HCN to benzaldehydeis ___.A. C8H7NO; B. C8H6NO; C. C14H11NO; D. C9H9NO; E. C9H8NO Please include all steps. Thank you!arrow_forward
- Predicting the qualitative acid-base properties of salts Consider the following data on some weak acids and weak bases: base acid K K a name formula name formula nitrous acid HNO2 4.5×10 hydroxylamine HONH2 1.1 × 10 8 hypochlorous acid HCIO 8 3.0 × 10 methylamine CH3NH2 | 4.4 × 10¯ 4 Use this data to rank the following solutions in order of increasing pH. In other words, select a '1' next to the solution that will have the lowest pH, a '2' next to the solution that will have the next lowest pH, and so on. 0.1 M KCIO solution PH choose one 0.1 M NaNO2 0.1 M CH3NH3Br 0.1 M NaBr choose one ✓ choose one v ✓ choose one 1 (lowest) ☑ 2 3 4 (highest)arrow_forwardFor this Orgo problem, don't worry about question 3 below it. Please explain your thought process, all your steps, and also include how you would tackle a similar problem. Thank you!arrow_forwardUsing the general properties of equilibrium constants At a certain temperature, the equilibrium constant K for the following reaction is 0.84: H2(g) + 2(g) 2 HI(g) = Use this information to complete the following table. Suppose a 34. L reaction vessel is filled with 0.79 mol of HI. What can you say about the composition of the mixture in the vessel at equilibrium? There will be very little H2 and 12. ☐ x10 There will be very little HI. Neither of the above is true. What is the equilibrium constant for the following reaction? Be sure your answer has the correct number of significant digits. 2 HI(g) H₂(9)+12(9) K = What is the equilibrium constant for the following reaction? Be sure your answer has the correct number of significant digits. 2 H2(g)+212(9) 4 HI(g) K = ☐ ☑arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
