1. Organic Chemistry Second Edition Chapter 13 David Klein
Alcohols and Phenols
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2. Please note:
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3. Section:  What is the correct IUPAC name for the following structure?      a. hexan-4-ol  b. hexanol  c. hexan-3-ol  d. 4-hexanol
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4. For more examples of this type of problem, see SkillBuilder 13.1.
Answer: c.
For more examples of this type of problem, see SkillBuilder 13.1.
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5. Section:  2. Which of the following structures represents 2-bromo-6-isobutyl-4-methyldec-3-en-1-ol?
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6. For more examples of this type of problem, see SkillBuilder 13.1.
Answer: d.
For more examples of this type of problem, see SkillBuilder 13.1.
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7.  Section: 13.2 3. Rank the following alcohols from STRONGEST to WEAKEST acids.
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8. For more examples of this type of problem, see SkillBuilder 13.2.
Answer: b, d, a, c.
For more examples of this type of problem, see SkillBuilder 13.2.
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9.  Section: Which of the following is not a reasonable resonance structure for the phenolate anion.
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10. Answer: c.
Make sure to follow the rules of resonance; around a benzene rings resonance form charges tend to move 2 carbons with every shift. For more examples of this type of problem, see SkillBuilder 13.2.
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11.  Section: What would be the primary explanation of the difference in acidity between the following alcohols?
Atom type
Induction
Resonance
Solvation
Orbital
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12. Answer: d.
Even differences in the ability of the alcohol functional group to be solvated based on differences in steric hindrance can change the acidity of a proton by two orders of magnitude. For more examples of this type of problem, see SkillBuilder 13.2.
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13. Section: 13.3 6. Which of the following reactions produce alcohols?
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14. For more examples of this type of problem, see SkillBuilder 13.2.
Answer: a, b, c, d, e
For more examples of this type of problem, see SkillBuilder 13.2.
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15. Alternate Answers: Section: 13. 3 6
 Alternate Answers: Section: Which of the following reactions produce alcohols?
a, b
a, b, c
a, b, c, d
a, b, c, e
a, b, c, d, e
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16. Answer: E
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17.  Section: 13.3 7. Which of the following reagents will complete the following?
Dilute H2SO4
1) Hg(OAc)2, H2O, 2) NaBH4
1) BH3.THF, 2) H2O2, NaOH
H3O+
H2O
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18. Answer: c
The only reagent that will easily complete an anti-Markovnikov hydration is the borane reagent system.
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19.  Section: 13.4 8. Rank the following from most highly oxidized highlighted C to most highly reduced.
1>2>3>4>5
2>4>3>5>1
1>5>3>4>2
4>2>5>3>1
1>3>5>2>4
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20. For more examples of this type of problem, see SkillBuilder 13.3.
Answer: b.
For more examples of this type of problem, see SkillBuilder 13.3.
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21. Section: Classify each of the following as oxidation, reduction or neither oxidation or reduction.
Oxidation
Reduction
Neither oxidation or
reduction
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22. For more examples of this type of problem, see SkillBuilder 13.3.
Answer: I: a, d, e
II: c, f
III: b
For more examples of this type of problem, see SkillBuilder 13.3.
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23. Alternate Answer: Section: 13. 4 9
Alternate Answer: Section: 13.4   9. Classify the following as oxidation, reduction or neither oxidation or reduction.
Oxidation
Reduction
Neither oxidation or
reduction
I: a, c, d; II: e, f; III: b
I: a, d, e; II: c, f; III: b
I: c, d, e; II: a, f; III: b
I: c, f; II: a, d, e; III: b
I: c, e; II: a, d, f; III: b
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24. Answer: b
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25. Section: 13.4 10. Classify the following as oxidation, reduction or neither oxidation or reduction.
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26. For more examples of this type of problem, see SkillBuilder 13.3.
Answer: I: b, c
II: a, f
III: d, e
For more examples of this type of problem, see SkillBuilder 13.3.
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27. Neither oxidation or reduction
Alternate Answers:  Section: Classify the following as oxidation, reduction or neither oxidation or reduction.
Oxidation
Reduction
Neither oxidation or reduction
I: a, b; II: c, d; III: e, f
I: a, b; II: e, f ; III: c, d
I: b, c; II: d, e; III: a, f
I: b, c; II: a, f; III: d, e
I: d, e; II: b, c; III: a, f
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28. Answer: d
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29. Section: 13.4 11. What is the product of the following reaction?
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30. Answer: d.
Reduction with H2 over platinum metal reduces all alkenes, ketones, and aldehydes fully and non-selectively. For more examples of this type of problem, see SkillBuilder 13.4.
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31. Section: 13.4 12. What is the product of the following reaction?
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32. Answer: d.
Reduction with sodium borohydride reduces only the ketone, not the acid. For more examples of this type of problem, see SkillBuilder 13.4.
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33. Section: 13.4 13. What is the product of the following reaction?
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34. Answer: d.
Reduction with lithium aluminum hydride reduces the ketone to a secondary alcohol and the ester to a primary alcohol. For more examples of this type of problem, see SkillBuilder 13.4.
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35. Section: 13.4 14. What is the product of the following reaction?
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36. Answer: d.
Reduction with lithium aluminum hydride reduces the ketone to a secondary alcohol and the carboxylic acid to a primary alcohol. For more examples of this type of problem, see SkillBuilder 13.4.
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37. Section: 13.4 15. What is the product of the following reaction?
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38. Answer: b.
Reduction with sodium borohydride reduces only the aldehyde not the ester. For more examples of this type of problem, see SkillBuilder 13.4.
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39. Section: 13.5 16. What reaction will give the highest yield of the anti-1,2,-diol shown below?
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40. Answer: c.
Only reactions with peroxy acids to form epoxides, followed by ring opening in an aqueous environment reliably forms anti-diols.
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41. Section: 13.6 17. What is the product of the following reaction?
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42. Answer: a.
Grignard reagents reduce ketones to alcohols while adding the alky group once. For more examples of this type of problem, see SkillBuilder 13.5.
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43. Section: 13.6 18. What is the product of the following reaction?
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44. Answer: b.
Grignard reagents react twice with esters to form a tertiary alcohol and adds two equivalents of the alkyl group. For more examples of this type of problem, see SkillBuilder 13.5.
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45. Section: 13.7 19. What is the correct order of reagents needed for the following transformation?
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46. Answer: c, h, a, b.
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47. Alternate Answer: Section: 13. 7 19
Alternate Answer: Section:  What is the correct order of reagents needed for the following transformation? g h
c, g, a, b
c, h, a, b
c, I, b
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48. Answer: D.
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49. Section: 13.8 20. What is the product of the following reaction?
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50. Cumene Hydroperoxide synthesis of phenol.
Answer: a.
Cumene Hydroperoxide synthesis of phenol.
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51. Section: 13.9 21. What is the product of the following reaction?
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52. Answer: d.
Addition of PBr3 to the alcohol inverts the stereochemistry. For more examples of this type of problem, see SkillBuilder 13.6.
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53. Section: 13.9 22. What is the product of the following reaction?
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54. Answer: b.
Thionyl chloride converts the alcohol to a chloride with inversion of configuration. For more examples of this type of problem, see SkillBuilder 13.6.
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55. Section: 13.7,  Which of the following give inversion of configuration when reacted with an alcohol?
 a. NaH, Tosyl chloride  b. TMS-Cl, imidazole, DMF  c. PBr3  d. A and B  e. A and C  f. B and C  g. all of the above  h. none of the above
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56. Answer: c.
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57. Alternate Answer: Section: 13. 7, 13. 9 23
Alternate Answer: Section: 13.7,  Which of the following give inversion of configuration when reacted with an alcohol?
NaH, Tosyl chloride
TMS-Cl, imidazole, DMF
PBr3
A and B
A and C
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58. Answer: C.
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59. Section: 13.10 24. What is the product of the following reaction?
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60. Answer: c.
Oxidation with PCC oxidizes primary alcohols to aldehydes and secondary alcohols to ketones. For more examples of this type of problem, see SkillBuilder 13.7.
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61. Section: 13.10 25. What is the product of the following reaction?
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62. Answer: b.
Oxidation with chromic acid turns primary alcohols into acids and secondary alcohols into ketones. For more examples of this type of problem, see SkillBuilder 13.7.
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63. Section: 13.12 26. What is the product of the following reaction?
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64. Phenol is readily oxidized to form benzoquinone.
Answer: e.
Phenol is readily oxidized to form benzoquinone.
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65. Section: 13.13 27. What is the product of the following reaction?
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66. Answer: b.
Hydroboration-oxidation gives the syn, anti-Markovnikov product. For more examples of this type of problem, see SkillBuilder 13.8 and 13.9.
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67. Section: 13.13 28. What is the product of the following reaction sequence?
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68. Answer: c.
For more examples of this type of problem, see SkillBuilder 13.8 and 13.9.
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69. Section: 13.13 29. What is the correct order of reagents needed for the following transformation?
a. 1) Hg(OAc)2, THF:H2O 2) NaBH4, OH– 3) TMS-Cl, Et3N
4) Potassium tert-butoxide 5) HBr/H2O2 6) TBAF
b. 1) NaBr/DMSO 2) Hg(OAc)2, THF:H2O 3) NaBH4, OH–
c. 1) Hg(OAc)2, THF:H2O 2) NaBH4, OH– 3) TMS-Cl, Et3N
4) Potassium tert-butoxide 5) BH3:THF 6) H2O2, OH– 7) PBr3
8) TBAF
 d. all of the above
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70. Answer: d.
All three reaction schemes give the same product. For more examples of this type of problem, see SkillBuilder 13.8 and 13.9.
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