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CHE 175 Spring, 2002 QUIZ 3 Name___________________________ ID (SSN)________________________ Instructor_______________________ SHORT ANSWER (10 pts each) 1. Rank the following compounds in order of decreasing acidity (1 = most acidic à 5 = least acidic): O O O O O H N O O 2. Show the enol tautomer of 1,3,5-cyclohexatrione. Would you expect this compound to exist predominantly in the keto or enol form? O O O 3. Show the major product that's formed from each of the reaction sequences shown below with cyclohexanone. 1. Me2NH 2. CH3CH2I O 1. LDA, -78 °C 2. CH3CH2I 3. H2O, H+ 4. Show a mechanism for the acid-catalyzed α-bromination of acetone. 5. Show how you would carry out the following synthesis. O O MULTIPLE CHOICE (10 pts each) 6. What is the carbon nucleophile that attacks molecular bromine in the acid-catalyzed α-bromination of a ketone? (a) an enolate (b) a carbocation (c) an acetylide (d) an enol 7. The Hell-Volhard-Zelinsky reaction involves: (a) the α-bromination of carboxylic acids (b) the α-bromination of ketones (c) the bromination of alcohols (d) none of the above O (a) O H (b) H O H (c) H3C H3C (d) all of these CH 3 8. Which of the following compounds does NOT have an α-hydrogen? 9. Which of the following is a β-ketoester? O OH (a) O (b) O OEt O O O (c) (d) O 10. What is the major product of the following reaction? O 1. LDA, -78 °C 2. CH3 I, -78 °C O (a) O (b) O OH (c) (d) **Bonus (+5 pts): Explain what "LDA" is, how to make it, and what it's used for. O O