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Full Organic Chemistry 5Th Edition Brown Test Bank Online PDF All Chapter
Full Organic Chemistry 5Th Edition Brown Test Bank Online PDF All Chapter
Full Organic Chemistry 5Th Edition Brown Test Bank Online PDF All Chapter
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CHAPTER 10--ALCOHOLS
Student: ___________________________________________________________________________
A. only 1
B. only 3
C. only 2 and 4
D. 1, 2, 3 and 4
4. Which of the following is/are primary (1) alcohols?
A. only 1
B. only 3
C. only 1 and 3
D. only 2, 3, and 4
A. 4-methyl-4-penten-1-ol
B. 2-methyl-1-penten-5-ol
C. 5-hydroxy-2-methyl-1-pentene
D. 4-methyl-5-penten-1-ol
A. 3-methyl-1-penten-4-ol
B. 3-methyl-4-penten-2-ol
C. 1,2-dimethyl-2-propan-1-ol
D. 2,3-dimethyl-1-propan-3-ol
7. What is the IUPAC name of the following compound?
A. cyclohexen-3-ol
B. cyclohexen-2-ol
C. 2-cyclohexenol
D. 3-cyclohexenol
A. 2-cyclopentenol
B. 3-cyclopentenol
C. cyclopenten-3-ol
D. cyclopenten-2-ol
A. cis-4-ethylcyclohexanol
B. trans-4-ethylcyclohexanol
C. cis-4-hydroxy-1-ethylcyclohexane
D. trans-4-hydroxy-1-ethylcyclohexane
10. What is the IUPAC name of the following compound?
A. cis-4-isopropylcyclohexanol
B. trans-4-isopropylcyclohexanol
C. cis-4-hydroxy-1-isopropylcyclohexane
D. trans-4-hydroxy-1-isopropylcyclohexane
A. (R)-2-methyl-4-pentanol
B. (S)-2-methyl-4-pentanol
C. (R)-4-methyl-2-pentanol
D. (S)-4-methyl-2-pentanol
A. (R)-2,2-dimethyl-3-pentanol
B. (S)-2,2-dimethyl-3-pentanol
C. 1-tert-butyl-1-propanol
D. (S)-4,4-dimethyl-3-pentanol
13. What is the IUPAC name of the following compound?
A. (E)-2-methyl-3-penten-2-ol
B. (Z)-2-methyl-3-penten-2-ol
C. (E)-4-methyl-2-penten-4-ol
D. (Z)-2-methyl-4-penten-2-ol
A. (E)-5-methyl-2-hexen-5-ol
B. (Z)-5-methyl-2-hexen-5-ol
C. (E)-2-methyl-4-hexen-2-ol
D. (Z)-2-methyl-4-hexen-2-ol
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
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
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
21. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
22. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
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
24. Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?
A. 1
B. 2
C. 3
D. 4
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
26. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
27. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
28. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
29. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
30. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
31. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
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
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
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)
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
36. Which of the following alcohols undergoes the most rapid dehydration upon treatment with H2SO4 to give
an alkene?
A. 1
B. 2
C. 3
D. 4
37. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
38. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
39. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
40. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
41. What is the major organic product obtained from the following reaction?
A. 1-butene, CH3CH2CH=CH2
B. butanal, CH3CH2CH2CHO
C. butanone, CH3CH2COCH3
D. butanoic acid, CH3CH2CH2COOH
42. What is the major organic product obtained from the following reaction?
A. 1-butene, CH3CH2CH=CH2
B. butanal, CH3CH2CH2CHO
C. butanone, CH3CH2COCH3
D. butanoic acid, CH3CH2CH2COOH
43. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
44. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
45. What is the major organic product obtained from the following reaction?
A. 1,6-hexanediol, HO(CH2)6OH
B. hexanedial, OHC(CH2)4CHO
C. hexanedioic acid, HO2C(CH2)4COOH
D. cyclohexene
46. What is the major organic product obtained from the following reaction?
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
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
49. What is the best choice of reagent to achieve the following transformation?
A. HCl
B. Cl2, light
C. SOCl2, pyridine
D. HOCl, H2O
50. What is the best choice of reagent to perform the following transformation?
A. HCl
B. NaOH
C. H2SO4
D. KMnO4
51. What is the best choice of reagent to perform the following transformation?
A. PCC
B. HIO4
C. CrO3
D. NaOH
52. What is the best choice of reagent to achieve the following transformation?
A. CrO3
B. NaOH
C. PCC
D. HIO4
53. What is the best choice of reagent to perform the following transformation?
A. HCl
B. NaOH
C. HIO4
D. PCC
54. What is the major organic product obtained from the following sequence of reactions?
A. 3-methyl-1-butene
B. 2-iodo-2-methylbutane
C. 1-iodo-3-methylbutane
D. 1-chloro-3-methylbutane
55. What is the major organic product obtained from the following sequence of reactions?
A. ()-2-azidopentane
B. (R)-2-azidopentane
C. (S)-2-azidopentane
D. (S)-2-pentyl tosylate
56. What is the correct assignment of the names of the following functional groups?
A. only 1
B. only 3
C. only 2 and 4
D. 1, 2, 3 and 4
4. Which of the following is/are primary (1) alcohols?
A. only 1
B. only 3
C. only 1 and 3
D. only 2, 3, and 4
A. 4-methyl-4-penten-1-ol
B. 2-methyl-1-penten-5-ol
C. 5-hydroxy-2-methyl-1-pentene
D. 4-methyl-5-penten-1-ol
A. 3-methyl-1-penten-4-ol
B. 3-methyl-4-penten-2-ol
C. 1,2-dimethyl-2-propan-1-ol
D. 2,3-dimethyl-1-propan-3-ol
7. What is the IUPAC name of the following compound?
A. cyclohexen-3-ol
B. cyclohexen-2-ol
C. 2-cyclohexenol
D. 3-cyclohexenol
A. 2-cyclopentenol
B. 3-cyclopentenol
C. cyclopenten-3-ol
D. cyclopenten-2-ol
A. cis-4-ethylcyclohexanol
B. trans-4-ethylcyclohexanol
C. cis-4-hydroxy-1-ethylcyclohexane
D. trans-4-hydroxy-1-ethylcyclohexane
10. What is the IUPAC name of the following compound?
A. cis-4-isopropylcyclohexanol
B. trans-4-isopropylcyclohexanol
C. cis-4-hydroxy-1-isopropylcyclohexane
D. trans-4-hydroxy-1-isopropylcyclohexane
A. (R)-2-methyl-4-pentanol
B. (S)-2-methyl-4-pentanol
C. (R)-4-methyl-2-pentanol
D. (S)-4-methyl-2-pentanol
A. (R)-2,2-dimethyl-3-pentanol
B. (S)-2,2-dimethyl-3-pentanol
C. 1-tert-butyl-1-propanol
D. (S)-4,4-dimethyl-3-pentanol
13. What is the IUPAC name of the following compound?
A. (E)-2-methyl-3-penten-2-ol
B. (Z)-2-methyl-3-penten-2-ol
C. (E)-4-methyl-2-penten-4-ol
D. (Z)-2-methyl-4-penten-2-ol
A. (E)-5-methyl-2-hexen-5-ol
B. (Z)-5-methyl-2-hexen-5-ol
C. (E)-2-methyl-4-hexen-2-ol
D. (Z)-2-methyl-4-hexen-2-ol
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
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
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
21. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
22. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
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
24. Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?
A. 1
B. 2
C. 3
D. 4
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
26. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
27. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
28. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
29. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
30. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
31. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
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
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
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)
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
36. Which of the following alcohols undergoes the most rapid dehydration upon treatment with H2SO4 to give
an alkene?
A. 1
B. 2
C. 3
D. 4
37. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
38. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
39. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
40. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
41. What is the major organic product obtained from the following reaction?
A. 1-butene, CH3CH2CH=CH2
B. butanal, CH3CH2CH2CHO
C. butanone, CH3CH2COCH3
D. butanoic acid, CH3CH2CH2COOH
42. What is the major organic product obtained from the following reaction?
A. 1-butene, CH3CH2CH=CH2
B. butanal, CH3CH2CH2CHO
C. butanone, CH3CH2COCH3
D. butanoic acid, CH3CH2CH2COOH
43. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
44. What is the major organic product obtained from the following reaction?
A. 1
B. 2
C. 3
D. 4
45. What is the major organic product obtained from the following reaction?
A. 1,6-hexanediol, HO(CH2)6OH
B. hexanedial, OHC(CH2)4CHO
C. hexanedioic acid, HO2C(CH2)4COOH
D. cyclohexene
46. What is the major organic product obtained from the following reaction?
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
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
49. What is the best choice of reagent to achieve the following transformation?
A. HCl
B. Cl2, light
C. SOCl2, pyridine
D. HOCl, H2O
50. What is the best choice of reagent to perform the following transformation?
A. HCl
B. NaOH
C. H2SO4
D. KMnO4
51. What is the best choice of reagent to perform the following transformation?
A. PCC
B. HIO4
C. CrO3
D. NaOH
52. What is the best choice of reagent to achieve the following transformation?
A. CrO3
B. NaOH
C. PCC
D. HIO4
53. What is the best choice of reagent to perform the following transformation?
A. HCl
B. NaOH
C. HIO4
D. PCC
54. What is the major organic product obtained from the following sequence of reactions?
A. 3-methyl-1-butene
B. 2-iodo-2-methylbutane
C. 1-iodo-3-methylbutane
D. 1-chloro-3-methylbutane
55. What is the major organic product obtained from the following sequence of reactions?
A. ()-2-azidopentane
B. (R)-2-azidopentane
C. (S)-2-azidopentane
D. (S)-2-pentyl tosylate
56. What is the correct assignment of the names of the following functional groups?