1. Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilicthan that of acetaldehyde? Explain using resonance structures.
2. Provide the structure of 4-oxohexanoic acid.
3. Give an IUPAC name to the following compound. Be sure to include configurational
information in the name.
4. Name the following compound.
5. Which of the following transitions is usually observed in the UV spectra of ketones?
A) n to π*
B) n to π
C) σ to n
D) σ to σ*
E) n to σ*
E) π to σ*
6. Predict the major organic product of the following reaction sequence.
7. Provide the major organic product which results when PhCHO is treated with the following
sequence of reagents:
8. Show how you would perform the following synthesis.
Copyright © 2017 Pearson Education, Inc.
9. The following compound has been found effective in treating pain and inflammation (J. Med.
Chem. 2007, 4222). Which sequence correctly ranks each carbonyl group in order of increasing
reactivity toward nucleophilic addition?
A) 1 < 2 < 3 B) 2 < 3 < 1 C) 3 < 1 < 2 D) 1 < 3 < 2 10. Provide a detailed, stepwise mechanism for the base-catalyzed hydration of 2-butanone. 11. Name the compound shown below. 12. Why can 1,2,2-trimethylaziridine be resolved into enantiomers while cannot? 13. Predict the product of the reaction shown below and add arrows to show the mechanism. 14. Devise an efficient method for preparing fluorobenzene from benzene. 15. Provide a detailed, stepwise mechanism for the reaction of acetyl chloride with methanol to produce methyl acetate and HCl. 16. Provide the major organic product of the reaction shown below and draw a mechanism that shows how it is formed. 2 Copyright © 2017 Pearson Education, Inc. 17. Provide a mechanism for the reaction shown below. 18. Provide the major organic product for the following reaction. 19. Provide a detailed, stepwise mechanism to show how PhCHO is formed by the reaction of PhCOCl with LiAlH [O(CH3)3]3. 20. What reagent is needed to complete the following transformation? 3 Copyright © 2017 Pearson Education, Inc.
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