Alcohols

Question 1

18. Which of the following best describes the reaction of sodium metal with methanol to give hydrogen and sodium methoxide?
    A. Lewis acid-base
    B. Brønsted-Lowry acid-base
    C. electrophile-nucleophile
    D. oxidation-reduction

Answer 1

D. oxidation-reduction

Question 2

19. What is the major organic product obtained from the reaction of 1-butanol with aqueous HBr at reflux?
    A. 1-bromobutane
    B. 2-bromobutane
    C. 2-bromo-1-butanol
    D. 1-butene

Answer 2

A. 1-bromobutane

Question 3

20. What is the major organic product obtained from the reaction of 2,2-dimethyl-1-propanol aqueous HBr at reflux?
    A. 1-bromo-2,2-dimethylpropane
    B. 1-bromo-2-methylbutane
    C. 2-bromo-2-methylbutane
    D. 3-bromo-2-methylbutane

Answer 3

C. 2-bromo-2-methylbutane

Question 4

21. What is the major organic product obtained from the following reaction?

Answer 4

D) 4

Question 5

22. What is the major organic product obtained from the following reaction?

Answer 5

B) 2

Question 6

23. Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?
    A. methanol
    B. ethanol
    C. 2-propanol
    D. 2-methyl-2-propanol

Answer 6

D. 2-methyl-2-propanol

Question 7

24. Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?

Answer 7

C. 3

Question 8

25. What type of reactive intermediate is formed in the reaction of 2-methyl-2-hexanol with HBr to give 2-bromo-2-methylhexane?
    A. an alkoxide
    B. a tertiary cation
    C. a tertiary radical
    D. a tertiary anion

Answer 8

a tertiary cation

Question 9

26. What is the major organic product obtained from the following reaction?

Answer 9

B. 2

Question 10

29. What is the major organic product obtained from the following reaction?

Answer 10

D. 4

Question 11

27. What is the major organic product obtained from the following reaction?

Answer 11

C. 3

Question 12

28. What is the major organic product obtained from the following reaction?

Answer 12

D) 4

Question 13

30. What is the major organic product obtained from the following reaction?

Answer 13

D) 4

Question 14

31. What is the major organic product obtained from the following reaction?

Answer 14

A) 1

Question 15

32. What is the major organic product obtained upon heating a mixture of 2-methylcyclopentanol and 85% H3PO4?
    A. 1-methylcyclopentene
    B. 3-methylcyclopentene
    C. 4-methylcyclopentene
    D. methylenecyclopentene

Answer 15

A. 1-methylcyclopentene

Question 16

33. What is the major organic product obtained upon heating a mixture of 3,3-dimethyl-2-butanol, (CH3)3CCH(OH)CH3, with sulfuric acid?
    A. 3,3-dimethyl-1-butene
    B. 2,3-dimethyl-1-butene
    C. 2,3-dimethyl-2-butene
    D. tert-butyl alcohol

Answer 16

C. 2,3-dimethyl-2-butene

Question 17

34. What is the major organic product obtained upon heating a mixture of 2-butanol and 85% H3PO4?
    A. 1-butene
    B. cis-2-butene
    C. trans-2-butene
    D. 2-methylpropene (isobutylene)

Answer 17

C. trans-2-butene

Question 18

35. Which of the following alcohols undergoes the most rapid dehydration upon treatment with H2SO4 to give an alkene?
    A. methanol
    B. ethanol
    C. 2-propanol
    D. 2-methyl-2-propanol

Answer 18

D. 2-methyl-2-propanol

Question 19

36. Which of the following alcohols undergoes the most rapid dehydration upon treatment with H2SO4 to give an alkene?

Answer 19

C. 3

Question 20

37. What is the major organic product obtained from the following reaction?

Answer 20

B. 2

Question 21

38. What is the major organic product obtained from the following reaction?

Answer 21

B) 2

Question 22

39. What is the major organic product obtained from the following reaction?

Answer 22

B. 2

Question 23

40. What is the major organic product obtained from the following reaction?

Answer 23

C. 3

Question 24

41. What is the major organic product obtained from the following reaction?

Answer 24

C. butanone, CH3CH2COCH3

Question 25

42. What is the major organic product obtained from the following reaction?

Answer 25

D. butanoic acid, CH3CH2CH2COOH

Question 26

43. What is the major organic product obtained from the following reaction?

Answer 26

C. 3

Question 27

44. What is the major organic product obtained from the following reaction?

Answer 27

B) 2

Question 28

45. What is the major organic product obtained from the following reaction?

Answer 28

hexanedial, OHC(CH2)4CHO

Question 29

46. What is the major organic product obtained from the following reaction?

Answer 29

acetaldehyde, CH3CHO

Question 30

47. What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with HCl to give tert-butyl chloride? A. tert-butyl radical B. tert-butyl anion C. tert-butyl cation D. tert-butoxide

Answer 30

tert-butyl cation

Question 31

48. What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H2SO4 to give methylpropene? A. tert-butyl cation B. tert-butyl anion C. tert-butyl radical D. tert-butoxide

Answer 31

tert-butyl cation

Question 32

49. What is the best choice of reagent to achieve the following transformation?

Answer 32

SOCl2, pyridine

Question 33

50. What is the best choice of reagent to perform the following transformation?

Answer 33

H2SO4

Question 34

51. What is the best choice of reagent to perform the following transformation?

Answer 34

HIO4

Question 35

52. What is the best choice of reagent to achieve the following transformation?

Answer 35

CrO3

Question 36

53. What is the best choice of reagent to perform the following transformation?

Answer 36

PCC

Question 37

54. What is the major organic product obtained from the following sequence of reactions?

Answer 37

1-iodo-3-methylbutane

Question 38

55. What is the major organic product obtained from the following sequence of reactions?

Answer 38

(R)-2-azidopentane

Question 39

56. What is the correct assignment of the names of the following functional groups?

Answer 39

1 = thiol; 2 = sulfinic acid; 3 = sulfonic acid