CHEM 2324 April 21, 2015 Exam 3 Version A Name: UTEP ID: 1.-5. Match each functional group centered on a given numbered carbon in the structure below to a best functional group name on the right. Answers may be repeated. O C1 O O C4 O C 2 O 1. 2. 3. 4. 5. C5 H O C3 H O C1 C2 C3 C4 C5 a. aldehyde b. enol ether c. ester d. ketal e. ketone 6.-10. Match each functional group centered on a given numbered carbon in the structure below to a best functional group name on the right. Answers may be repeated. Interestingly, this compounds looks a lot like a common sedative. OH O H C8 C7 C9 N N H C6 C10 H 6. 7. 8. 9. 10. N C6 C7 C8 C9 C10 a. nitrile b. imine c. enamine d. cyanohydrin e. amide Assume any necessary workup for the following reactions: 11.-15. Order the reactants, intermediates, and final product of the reaction of methyl ethanoate and excess Grignard reagent of iodomethane. Counter ions, byproducts, non-bonding electrons, and charges are not shown. 11. 12. 13. CH3 CH3 a. O CH3 O b. CH3 O CH3 CH3 14. CH3 c. CH3 O CH3 15. O d. OH CH3 CH3 CH3 CH3 O e. CH3 CH3 16. The product of 1-chloropropane and magnesium reacts with butanone to make mostly? a. 2-propylbutan-2-ol b. 2-ethylpentan-2-ol c. 3-methylhexan-3-ol d. heptan-4-ol e. not a.-d. 17. The product of 2-chloro-2-methylpropane and magnesium reacts with carbon dioxide to make mostly? a. 3-methylbutan-2-one b. 2,2-dimethylpropanoic acid c. 2-methylbutanoic acid d. 2,2-dimethylpropanal e. not a.-d. 18. Ignoring E or Z isomers, the product 1-chloropropane, triphenylphospine, and base reacts with butanone to make mostly? a. 2-propylbut-2-ene b. 2-ethylpent-2-ene c. 3-methylhex-3-ene d. 4-methylhex-3-ene e. not a.-d. 19. The reaction of 2-methylpropanal, ammonia, sodium cyanoborohydride, and acid catalysis makes mostly? a. NH2 NH2 NH2 b. c. NH2 d. e. not a.-d. 20. The reaction of propanone and dimethylamine ((CH3)2NH) makes mostly? N a. N b. c. N d. N e. not a.-d. 21. The reaction of propanal, ethane-1,2-diol, and acid catalysis makes mostly? O O b. O a. O O O c. O d. O e. not a.-d. 22.-26. Match each set of reagents to a major product on the right. Answers may be repeated. Assume any necessary workup between steps. 22. butanoic acid + thionyl chloride + pyridine catalysis followed by methanol a. butanamide 23. sodium butanoate + hydrochloric acid followed by methanol + acid catalysis b. butanenitrile 24. methyl butanoate + ammonia followed by thionyl chloride + heat c. butanoyl chloride 25. butanamide + water + acid catalysis followed by thionyl chloride + pyridine catalysis d. methyl butanoate 26. butanoic acid + heat followed by excess ammonia e. not a.-d. 27.-33. Match each set of reagents to a major product below. Answers are repeated. Assume any necessary workup between steps. Extra space is provided so that you can draw your intermediates. 27. ethanoic acid + diazomethane followed by excess methyl magnesium chloride 28. butanoic acid + dimethylamine + dicyclohexylcarbodiimide followed by diisobutylaluminum hydride followed by sodium borohydride 29. propanoic acid + sodium hydroxide followed by methyllithium followed by sodium borohydride 30. ethanoic acid + thionyl chloride + pyridine catalysis followed by tri-tert-butoxyaluminum hydride followed by ethyl magnesium bromide 31. 2-methylpropanoic + thionyl chloride + pyridine catalysis followed by sodium 2-methylpropanoate followed by lithium aluminum hydride 32. propanoic acid + ammonia + heat followed by thionyl chloride + heat followed by methyl magnesium chloride followed by water + acid catalysis followed by sodium borohydride 33. butanoic acid + ammonia followed by heat followed by lithium aluminum hydride a. OH OH OH b. c. d. OH e. not a.-d. If required, the Exam 3 retake homework will be due Friday, April 24, before 5 pm through http://organic.utep.edu/quiz, no exceptions or excuses. These sheets will be available in CCSB 2.0702 after 1 pm today. Put your name on these sheets so that you can recover your class answers. An exam file will also be available from http://organic.utep.edu/courses/2324/exams. Expect an email from me this evening.