CHE 325

ALCOHOLS, DIOLS, AND THIOLS

CHAP 15 ASSIGN

1. Which of the following cannot be made by the reduction of a ketone or aldehyde with NaBH 4 in methanol? A. 1-butanol B. 2-butanol C. 2-methyl-1-propanol D. 2-methyl-2-propanol

2. An alcohol has the same oxidation state as a(n) A. ketone. B. alkene. C. organolithium compound. D. alkyl halide.

3. What is the product of the following reaction?

4. Which one of the following is not readily oxidized by K 2Cr2O7 in H2SO4/H2O? A. 1-butanol B. sec-butyl alcohol C. 2-methyl-1-propanol D. 2-methyl-2-butanol

5. Identify the reagent needed to carry out the following conversion. A. B. C. D. E. F. K2Cr2O7, H2SO4/H2O PCC/CH2Cl2 OsO4, (CH3)3COOH, (CH3)3COH, OHNa2Cr2O7/H2SO4 / H2O NaBH4 LiAlH4

6. Which one of the following diols would cleave into two fragments with HIO 4? A. 1,3-hexanediol B. 2,4-hexanediol C. 3,4-hexanediol D. 1,6-hexanediol

7. Compound A, C6H12O, is readily oxidized with K2Cr2O7 in H2SO4/H2O to give compound B, C6H10O. Compound B has four peaks in its C-13 NMR (broadband decoupled). Which one of the following fits the data for compound A?

8. The alcohol product(s) of the reduction of 2-methyl-3-pentanone with LiAlH4 is(are) A. B. C. D. a single enantiomer. a racemic mixture. two diastereomers. two constitutional isomers.

9. Which of the following syntheses gives 3-methyl-1-hexanol?

10. Which of the following is the ester formed between methanol and nitric acid, HNO 3?

11. (2R ,3S )-3-Bromo-2-methyl-1-butanol is the IUPAC name for which of the following alcohols?

12. What is the product of the reaction below?

13. Which of the following reagents will convert cyclohexene into cis-1,2-cyclohexanediol? A. OsO4, (CH3)3COOH, (CH3)3COH, OH C. O3 followed by Zn/H2O B. HIO4 D. CH3CO3H (peroxyacetic acid)
2

14. What is the product of the following reaction sequence? A. B. C. D. cyclopentene oxide cyclopentene cyclopentane cis-1,2-cyclopentanediol

15. To which side, if any, would the reaction below lie? A. B. C. D. to the right to the left equally to both sides this reaction cannot occur

16. The lithium aluminum hydride reduction of this ester would yield:

1. LiAlH4 O O 2. H2O

17. What product(s) would you expect from the following reaction?

18. Which one of the following reaction steps work best to carry out the transformation shown below?

19. What is the major product of the following reaction?

A.

B.

C.

D.

E.

20. Which of the following would be true of the reaction shown?

A. A carbon is oxidized in this reaction. C. The bromine is oxidized in this reaction. E. This cannot be considered as an oxidation/reduction reaction. 21. What is the major product of the following reaction?

B. A carbon is reduced in this reaction. D. The bromine is reduced in this reaction.

A.

B.

C.

D.

E.

22. What is the correct IUPAC name of the following molecule? A. B. C. D. E. 5-(hydroxyethyl)-decane 3-butyl-1-octanol 5-pentyl-1-heptanol 6-butyl-1-octanol 3-butyl-3-pentyl-1-propanol

23. What is the proper name of the molecule shown? A. B. C. D. E. 2-methyl-4-pentanol 1,3-dimethyl-1-butanol 4-hydroxy-2-methylpentane 4-methyl-2-pentanol 2-hydroxy-4-methylpentane

24. Which statement is generally true about the reaction shown below?

A. B. C. D. E.

This is an equilibrium that generally lies to the right. This is an equilibrium that generally lies to the left. This is an equilibrium that lies equally to both sides. This is not an equilibrium reaction. There is no way to know to which side this reaction usually lies.

25. Which of the following reactions would you expect to produce 2-pentanol?

A.

B.

C.

D. All of these reactions would produce 2-pentanol. E. Only two of these reactions would produce 2-pentanol. Which ones? 26. What reagent(s) would be appropriate to accomplish the conversion shown? A. HCl B. HNO3 C. H2SO4 D. HBr E. K2Cr2O7 + H2SO4 27. What is the major product of the following reaction?

28. What reagents would you use to carry out the following reaction?

29. Which of the following would NOT efficiently accomplish the reaction shown? A. B. C. D. E. NaH Na (metal) NH2 K (metal) OH

30. Predict the major product of the following reaction.

31. Which of the following reactions could be used to make cyclohexanecarbonitrile from cyclohexanol?

Two of these would work. Which ones?

32. If the following reaction proceeds as indicated, what mechanistic pathway does it most likely follow? A. B. C. D. E. E2 E1 S N2 S N1 free-radical halogenation

33. What major product would you expect from the following reaction?

C
6

34. What was the intended product of this reaction sequence?

35. Predict the major product of the following reaction.

EXTRA CREDIT
36. The tertiary alcohol below was reacted with PCC in CH2Cl2 and gave a product, C12H12O. The product had a strong absorption in the IR spectrum at 1700 cm-1. Predict which of the following is the product. (Note: PCC is pyridinium chlorochromate, [C5H5NH+][ClCrO3].)

37. What is the final product of the following reactions? A. B. C. D. 2,3-dimethyl-3-pentanol 2,3-dimethyl-2-pentanol 2,4-dimethyl-3-pentanol 2,2-dimethyl-3-pentanol

38. What is the product of the synthetic sequence below?

NAME_______________________________________ ANSWER SHEET CHE 325 CHAP 15 ASSIGN 1. _______________ 2. _______________ 3. _______________ 4. _______________ 5. _______________ 6. _______________ 7. _______________ 8. _______________ 9. _______________ 10. _______________ 11. _______________ 12. _______________ 13. _______________ 14. _______________ 15. _______________ 16. _______________ 17. _______________ 18. _______________ 19. _______________ 20. _______________ 21. _______________ 22. _______________ 23. _______________ 24. _______________ 25. _______________ 26. _______________ 27. _______________ 28. _______________ 29. _______________ 30. _______________ 31. _______________ 32. _______________ 33. _______________ 34. _______________ 35. _______________ 36. _______________

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37. _______________ 38. _______________ 39. _______________ 40. _______________ 41. _______________ 42. _______________ 43. _______________ 44. _______________ 45. _______________ 46. _______________ 47. _______________ 48. _______________
SS II 2012