CHEM 2324Exam 3Version AName:

April 23, 2013UTEP ID #:

1.-5. Order the reagents, intermediates, and products of the reaction of a tertiary amide with diisobutylaluminum hydride followed by hydronium workup. For brevity the isobutyl group is shown as R, and charges and electrons are not shown.

1.2.3.4.5.

a. b. c. d. e.

6.-10. Match each structure to a functional group type below. Answers may be repeated.

6. 7. 8. 9. 10.

a. enol b. hemiacetal c. ketald. oxoniume. not a.-d.

11.-15. Match each set of reactants on the left to a major product on the right. Assume any necessary workup. Answers may be repeated.

11. ethanal and hydrazine a.

12. ethanal and a primary amineb.

13. ethanal and hydrogen cyanide c.

14. ethanal and a secondary amined.

15. ethanal, a primary amine, acid, and sodium cyanoborohydride e. not a.-d.

  1. Which compound cannot be made by reacting sodium borohydride with an aldehyde or ketone and appropriate workup?

a. methanolb. ethanolc. propan-2-old. 2-methylpropan-2-ole. not a.-d.

  1. Which compound cannot be made by reacting methylmagnesium chloride with an aldehyde or ketone and appropriate workup?

a. methanolb. ethanolc. propan-2-old. 2-methylpropan-2-ole. not a.-d.

  1. What is the thirdintermediate in the reaction of iodoethane, triphenylphosphine, n-butyllithium, and ethanal? Ph = phenyl. Electrons and charges are not shown.

a. b. c. d. e.

19.-23. Match each set of reactions on the left to a major product on the right. Do the reactions in parenthetic order. Assume any necessary workup after each step. Answers may be repeated.

  1. (methyl ethanoate + water (acid catalysis)) + CH2N2a.
  2. (methyl ethanoate + sodium hydroxide) + ethanoyl chlorideb.
  3. (ethanoic acid + heat) + sodium hydroxidec.
  4. (ethanoic acid + thionyl chloride (pyridine catalysis)) + H2Od.
  5. (ethanoic acid + thionyl chloride (pyridine catalysis)) + NaOCH3e. not a.-d.

24.-26. Match each set of reactions on the left to a final product on the right. Do the reactions in parenthetic order. Assume hydronium workup at the end.Answers may be repeated.

  1. (CH3CH2I + 2 Li) + CO2 + 2(CH3I + 2 Li)a.
  2. ((propanoic acid + ammonia + heat) + SOCl2 + heat) + (CH3I + Mg)b.
  3. (propanoic acid + SOCl2 (pyridine catalysis)) + (2 (CH3I + 2 Li) + CuI)c.

d.

e. not .a-d.

  1. If you reacted a one to one ratio of propanoic anhydride and ammonia, and without workup reacted with excess lithium aluminum hydride, which compound would you not make?

a. NH3b.c.d.e. not a.-d.

You can pick up these sheets from CCSB 2.0702 starting today after 1 p.m. Please put your name on these sheets and on your Scantron. Only your Scantron will count for a grade. If necessary, the Exam 3 homework will be due via by Friday, April 26, before 5 p.m., no exception! Expect an email from me.