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1 Q1 A B C E F - None of these products are a major product of the reaction that is shown.

2 Q1 A B C E F - None of these products are a major product of the reaction that is shown.

3 Exam 3 Time: Tuesday, November 8: 7:00 9:00PM OR Wednesday, November 9: 7:00 9:00PM OR Thursday, November 10: 7:00 10:00PM Location Soc/Anthro Testing Center Chapters will be covered in this order: Chapter 17, 18 Practice Exams are Posted Ex3A Practice Exam 3A Ex3B Practice Exam 3B eadline for alternate arrangements is Monday, 11/7/2016 at 4:30 PM (i.e., close of business) An oral make-up exam will be required for making up the exam for all students not taking the exam on the above dates or having already made prior arrangements

4 Exam 3 Lecture Planning Ex3-01-B A Ketone Aldehyde Naming Friday, October 22 Ex3-01-B B Aldehyde Ketone Naming Saturday, October 22 Ex3-02-B A Ald Ket Rxns O-Nucl Saturday, October 23 Ex3-02-B B Ald Ket O-Nucleophiles Sunday, October 24 Ex3-02-B C Ald Ket Rxns O-Nucl Monday, October 25 Ex3-03-B A Ald Ket with N-Nucl Tuesday, October 26 Ex3-03-B B Ald Ket with N-Nucl Wednesday, October 27 Ex3-03-B C Ald Ket with N-Nucl Thursday, October 28 Ex3-04-B A Ald Ket with C-Nucl Friday, October 29 Ex3-04-B B Ald Ket with C-Nucl Saturday, October 29 Ex3-04-B C Ald Ket with C-Nucl Sunday, October 30 Ex3-05-B Tautomers Sunday, October 30 Ex3-06-B B Alpha-Bromination Monday, October 31 Ex3-06-B C Alpha-Bromination Tuesday, November 1 Ex3-07-B B Alkylation Alpha-C=O Wednesday, November 2 Ex3-07-B C Alkylation Alpha-C=O Thursday, November 3 Ex3-08-B B Malonic Ester Synthesis Friday, November 4 Ex3-08-B C Malonic Ester Synthesis Saturday, November 5 Ex3-09-B Fatty Acids Sunday, November 6 Exam 3 November 8, 9, 10

5 Q2 A B C E F - None of these products are a major product of the reaction that is shown.

6 Methyl ketone Too high in energy X

7 Q2 A B C E F - None of these products are a major product of the reaction that is shown.

8 No Class Friday

9 alphabetical order. (Example: xxxx ab) Q3 CH3CH2I H3O + A B C E - None of these products are a major product of the reaction that is shown.

10 alphabetical order. (Example: xxxx ab) Q3 CH3CH2I H3O + A B C E - None of these products are a major product of the reaction that is shown.

11 alphabetical order. (Example: xxxx ab) Q4 CH 3 I H3O + A B C E - None of these products are a major product of the reaction that is shown.

12 alphabetical order. (Example: xxxx ab) Q4 CH 3 I H3O + A B C E - None of these products are a major product of the reaction that is shown.

13 no reaction no reaction enol

14 Which of the following compounds would be expected to eliminate CO 2 when ed? Q5 A B C E F

15 Which of the following compounds would be expected to eliminate CO 2 when ed? Q5 A B C E F

16 Malonic Ester Synthesis Any substitutable halide CH3I (1 mole)

17 Final Product epends on Work-up Conditions CH3OH CH3OH H3O + - OH CH3OH - OH H3O + CH3OH - OH H3O + CH3OH CH3OH

18 alphabetical order. (Example: xxxx ab) A B C E - None of these products are a major product of the reaction that is shown Q6

19 alphabetical order. (Example: xxxx ab) A B C E - None of these products are a major product of the reaction that is shown Q6

20 alphabetical order. (Example: xxxx ab) 1) NaOMe 2) CH3I 3) H3O +,? A B C E F G H - None of these products are a major product of the reaction that is shown Q7

21 alphabetical order. (Example: xxxx ab) 1) NaOMe 2) CH3I 3) H3O +,? A B C E F G H - None of these products are a major product of the reaction that is shown Q7

22 Consider the biological reaction shown below which converts fatty acids to larger fatty acids. Give the Correct identities for 1, 2, 3, and 4 in that order. (Example: xxxx ab) CoA CoA CoA A CoA B CoA CoA C CoA E

23 Consider the biological reaction shown below which converts fatty acids to larger fatty acids. Give the Correct identities for 1, 2, 3, and 4 in that order. (Example: xxxx ab) CoA CoA 4 CoA A CoA B CoA CoA C CoA E

24 NaOMe H 3 O +? A B C E - None of these products are a major product of the reaction that is shown.

25 NaOMe H 3 O +? A B C E - None of these products are a major product of the reaction that is shown.

26 NaOMe H3O +? A B C E - None of these products are a major product of the reaction that is shown.

27 HCN A B C - None of these products are a major product of the reaction that is shown.

28

29 ? A B C E F - None of these products are a major product of the reaction that is shown.

30 NaNH2 A B C E F G - None of these products are a major product of the reaction that is shown.

31 H +? A B C E - None of these products are a major product of the reaction that is shown.

32 NaOMe NaOH H3O + A B C E - None of these products are a major product of the reaction that is shown.

33 Ph 3 P + CH 3 Br - n-buli? A B E - None of these products are a major product of the reaction that is shown. C

34 + NaOMe CH3Br (1 mole) NaOH H3O + A B C E F G - None of these products are a major product of the reaction that is shown.

35 Q2 A B C E F G - None of these products are a major product of the reaction that is shown.

36 Q2 A B C E F G - None of these products are a major product of the reaction that is shown.

37 Give the minor organic product(s) of the following reaction. Give your Q3 A B C E F G - None of these products are a major product of the reaction that is shown.

38 Give the minor organic product(s) of the following reaction. Give your Q3 A B C E F G - None of these products are a major product of the reaction that is shown.

39 Lithium i-isopropylamide (LA) H2 A. Strong base (N - is not that happy, since N is not that electronegative and doesn t want a negative charge) B. Non-nucleophilic, b/c of steric hindrance of isopropyl groups

40 LA as a base for H s α to a carbonyl 1) LA (1 mole) 2) 3) H + (work-up)

41 Q4 A B C E F - None of these products are a major product of the reaction that is shown.

42 Q4 A B C E F - None of these products are a major product of the reaction that is shown.

43 1) Br2, PBr3, 2) H3O Q5 A B C E F G - None of these products are a major product of the reaction that is shown.

44 1) Br2, PBr3, 2) H3O Q5 A B C E F G - None of these products are a major product of the reaction that is shown.

45 1) A B 2) NaOH, H2O Q11 C E F G H I - None of these products are a major product of the reaction that is shown.

46 1) Li 2) A B Q12 3) H + E - None of these products are a major product of the reaction that is shown. C

47 1) Q2 2) H + A B C E F G H - None of these products are a major product of the reaction that is shown.

heat E Q1

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