MC Practice Exam

Spring 2015 Final Exam Review

1. What is the multiplicity expected in the hydrogen NMR spectrum for the hydrogen atoms marked by a "star" in the following compound?

A) SingletB) TripletC) QuartetD) Sextet

2. Rank the following alcohols from most acidic to least acidic.

A) I>II>IV>IIIB) II>III>IV>IC) III>IV>II>ID) IV>III>I>IIE) IV>I>III>II

3. Predict the product of the following reaction:

a. b. c. d.

4. Predict the product

A) B) C)

Disclaimer: This is not meant to be representative of what your exam will be like. This is simply a review your loving TAs put together for you.


5. Arrange the following compounds in order of decreasing chemical shift for the underlined hydrogens (higher ppm to lower ppm).

CH3CH2CH3 CH3OCH2CH3 Cl2CHCH2CH3 ClCH2CH2CH3

a b c d

A) b > c > a > dB) b > c > d > aC) c > b > a > dD) c > b > d > a

6. Choose the best reagent set for achieving the following transformation.

A) PCCB) Na2Cr2O7, H2SO4, H2OC) KMNO4

D) All of the above

7. Which of the following molecules can NOT decarboxylate?

A) A only B) B only C) C only D) Both A and B

8. Which reagent(s) should you use to accomplish the following transformations?

A) B) C) D)

NaBH4 then NH3, excess


9. How many signals would the following molecule show in its 1H NMR spectrum?

a. 5b. 1c. 6d. 8

10. What is the product of the following reaction?

A)

B)

C)

D)

11. Which set of reagents is appropriate to convert the benzyl bromide to the corresponding carboxylic acid?

A) Mg, Et2O then CO2 then H3O+ B) NaCN then H3O+ c) a or b d. Na2Cr2O7

12. Which reagent(s) should you use to complete the following transformation?

A) OsO4

B) Acid, methanolC) Williamson’s reagent


D) NaOMe, MeOH

13. An unknown molecule A has 4 signals in the 1H NMR spectrum. Which of the following corresponds to molecule A?

a. b. c. d.

14. Which of the following ethers cannot be prepared by a Williamson ether synthesis?A) tert-butyl phenyl etherB) isopropyl methyl etherC) anisoleD) tert-butyl methyl ether

15. What is the product when the following lactone is treated with aqueous sodium hydroxide?

a. b. c. d.

16. Which is the strongest reducing agent?A) PCCB) KMnO4

C) NaBH4

D) LiAlH4

17. Propose a structure for the following compound. 1H NMR spectrum of C5H8O2: δ 1.90 (multiplet, 4H); δ 2.40 (triplet, 2H); δ 4.26 (triplet, 2H)

a. b. c. d.


18. Synthesis of hexane-3,4-diol from (E)-3-hexene can be accomplished in two ways:i. OsO4 hydroxylation

ii. C6H5CO3H epoxidation followed by NaOH expoxide ring openingWhich of the following statements about the products from these reactions is correct?

A) the two methods give the same productB) (a) gives a chiral isomer, (b) gives an achiral isomerC) (a) gives an achiral isomer, (b) gives a chiral isomerD) two different isomers are formed, but both are chiral

19. Which of the following carboxylic acid derivatives is most difficult to hydrolyze?

a. b. c. d.

20. Which compound is the most basic? A) B) C) D)

21. How many tautomers can you draw for the following diketone?

A) 1B) 2C) 3D) 4

22. Which set of reagents would accomplish the following transformation?

A) OsO4, then IO4 B) O3, then H2O2 C) mCPBA (2 eq) D) PCC


23. Which of the following is a D-ketopentose.

A) IB) IIC) IIID) IVE) I and III

24. What is the product of the following reaction?

A) B) C) D)

25. What is the final product of the following reaction?

a. b. c. d.

26. Which conditions will give you exclusively the following compound from D-glucose?

A) MeI, NaOHB) MeOH, HClC) NaOMe, MeOHD) MeI, pyridine


27. Which pi-bond will be reduced first when treated with H2(g) and Pd0?A) B) C)

28. Which set of reagents would accomplish the following transformation?

A) B) C) D) both b and c

29. Choose the reagent(s) to accomplish the following transformation:

A) MgBrCH3, CO(g)B) Sharpless dihydroxylationC) NaCN, then acidD) LiAlH4, PCC

30. Give the major product of the following reaction.

a. b. c. d.

31. Which is the correct product?

A) B) C) D)


32. Identify the α-linked disaccharides.

A) I B) IIC) IVD) III and IVE) I and II

33. Acid chlorides are especially useful for:A) nucleophilic acyl addition reactions B) electrophilic acyl addition reactionsC) nucleophilic acyl substitution reactions D) electrophilic acyl substitution reactions

34. What starting material is required for the following reaction?

a. b. c. d.

35. Which of the following can be identified as anomers?

A) I and IIB) I and IIIC) I and IVD) II and IIIE) III and IV

36. Acids can be converted to primary amines by:A) conversion to the nitrile followed by treatment with LiAlH4

B) conversion to the diazonium salt followed by treatment with NaBH4

C) conversion to the primary amide followed by treatment with LiAlH4

D) both A and BE) Both A and C


37. What is the product of the following sequence:

38. Which two of the following compounds are reduced to the same chiral alditol by sodium borohydride?

A) I and IIB) II and IIIC) III and IVD) II and III

39. Predict the major products of the following reaction:

A) B)


C) D)40. How would you make this?

A.) 1. NH3, HCN 2. H3O+, H2O, heat 3. NaOH 4. NeutralizeB.) 1. NH3

2. H3O+, H2O, heat

41. Which of the following compounds corresponds to the IR spectrum shown below?

42. The following transformation can be accomplished with the use of which of the reagents below?

A) H2N-NH2, DCMB) NH3, H2OC) NH3, MeOHD) Me2NH, DCM


43. Which of the following compounds corresponds to the 1HNMR spectrum below?

44. Which compound is the product of an aldol condensation?

45. What would be the product of the following reaction?


46. Propose a synthesis for the following:


(3 steps)




Answers:1. C2. E3. B4. A5. B6. A7. B8. B9. A10. C11. C12. B13. C14. A15. D16. D17. D18. C19. B20. A21. C22. B23. A24. B25. D26. B27. D28. B29. C30. B31. A32. E33. C34. C35. A36. E37. C38. A39. B40. A41. A42. D43. E44. A


45. B46.

47.


48.

49.

50. ?

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MC Practice Exam