CHEM 2425. Chapter 23. Carbonyl Condensation Reactions (quiz) W25 Student: 1. Which of the following statements about Aldol reactions with either aldehydes or ketones is true? Equilibrium favors the starting materials with aldehydes; equilibrium favors the products with ketones. Equilibrium favors the products with aldehydes; equilibrium favors the starting materials with ketones. Equilibrium favors the starting materials with both aldehydes and ketones. Equilibrium favors the products with both aldehydes and ketones. 2. In a Michael reaction, where does the nucleophile attack the a,b-unsaturated carbonyl component? Carbonyl carbon a-carbon Carbonyl carbon and b-carbon b-carbon 3. What is the product of the following Claisen reaction? IV I III
4. Would this crossed Aldol reaction work well? Why or why not? Yes, the diketone is significantly more acidic, so this enolate can be formed selectively. No, the diketone is significantly more acidic, so this enolate cannot be formed selectively. Yes, the aldehyde is significantly more acidic, so this enolate can be formed selectively. No, the aldehyde is significantly more acidic, so this enolate cannot be formed selectively. 5. What is an intramolecular Claisen reaction called? Robinson reaction Dieckmann reaction Hoffman reaction Michael reaction 6. What reaction type is a Claisen reaction? Electrophilic substitution Nucleophilic addition Electrophilic addition Nucleophilic substitution 7. What product (including stereochemistry) is formed in the following intermolecular reaction? IV I III
8. Which of the following compounds can undergo an Aldol with itself? I III Both I and II 9. There are several variations of the Aldol reaction. Which of the following types of reactants leads to only one possible product with the Aldol condensation reaction? Any aldehyde and ketone mixed together can react to form a single condensation product. Two different ketones with a-hydrogens are able to form a single aldol condensation product. Any pair of aldehyde or ketone reactants where one of the reactants has no a-hydrogens will lead to a single aldol product. Two different aldehydes with a-hydrogens are able to form a single aldol condensation product. 10. What is the name given to an Aldol reaction between two different carbonyl compounds? Multiple Aldol reaction Crossed Aldol reaction Differential Aldol reaction Versatile Aldol reaction 11. What is the general name for the class of products formed in an Aldol condensation reaction? a,g-unsaturated carbonyl compound a,b-unsaturated carbonyl compound b,g-unsaturated carbonyl compound b-hydroxy carbonyl compound
12. Complete this statement: A major difference between the Aldol condensation and the Claisen condensation reactions is that the Aldol reaction is base catalyzed while the Claisen reaction requires a full equivalent of base. the Aldol reaction is acid catalyzed while the Claisen reaction is base-catalyzed. the Aldol reaction involves substitution while the Claisen reaction involves addition. the Aldol reaction is base catalyzed while the Claisen reaction is acid-catalyzed. 13. The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product; what is the explanation for this result? Hydroxide is eliminated via an enolate intermediate. The hydroxy group is oxidized to a carbonyl. The hydroxy group reacts with the carbonyl to form a ketal. It undergoes elimination, since water is a good leaving group. 14. In what situation can the yield of a single crossed Aldol product be increased? The nucleophilic carbonyl component is relatively hindered and is used in limited amount. The electrophilic carbonyl carbon component is relatively hindered and is used in limited amount. The electrophilic carbonyl component is relatively unhindered and is used in excess. The nucleophilic carbonyl component is relatively unhindered and is used in excess. 15. The following reaction is an example of what type of reaction? Claisen condensation Dieckmann condensation Mixed Aldol reaction Robinson annulation
16. What is the Aldol addition product formed from the reaction of acetone, (CH 3 ) 2 CO,withitself? III I IV 17. Complete this statement: A major difference between the Aldol condensation and the Claisen condensation reactions is that the Aldol reaction is base catalyzed while the Claisen reaction requires a full equivalent of base. the Aldol reaction is acid catalyzed while the Claisen reaction is base-catalyzed. the Aldol reaction involves substitution while the Claisen reaction involves addition. the Aldol reaction is base catalyzed while the Claisen reaction is acid-catalyzed. 18. What is the name given to the Claisen reaction between two different esters? Versatile Claisen reaction Crossed Claisen reaction Differential Claisen reaction Multiple Claisen reaction
19. Which is the unsaturated carbonyl compound formed in the dehydration of the following b-hydroxy carbonyl compound? I and II I None of the choices 20. What is the Aldol addition product formed from reaction of the following compound with itself? III I IV
21. What cyclic product is formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH? I I IV II 22. What are the two starting materials for a Robinson annulation? an a,b-unsaturated carbonyl compound and an enolate a 1,3-Dicarbonyl compound and an enolate a 1,5-Dicarbonyl compound and an enolate a b-ketoester and an enolate 23. Which of the following carbonyl compounds does not undergo Aldol addition reactions when treated with aqueous sodium hydroxide? III IV I II
24. What is the general name of the product of a crossed Claisen reaction between a ketone and an ester? a,b-dicarbonyl compound b-dicarbonyl compound g-dicarbonyl compound b-keto ester 25. What is the general name for the reaction product formed in an aldol addition reaction? b-hydroxy carbonyl compound g-hydroxy carbonyl compound a,b-hydroxy carbonyl compound a-hydroxy carbonyl compound