Deck 10: Alcohols

Question 1

Which of the following is/are primary (1 $\degree$ ) alcohols?

A) only 1
B) only 3
C) only 1 and 3
D) only 2, 3, and 4

Answer 1

only 3

Question 2

Which of the following has the highest boiling point?

A) pentane
B) methyl propyl ether
C) diethyl ether
D) 1-butanol

Answer 2

1-butanol

Question 3

What is the IUPAC name of the following compound?

A) cyclohexen-3-ol
B) cyclohexen-2-ol
C) 2-cyclohexenol
D) 3-cyclohexenol

Answer 3

2-cyclohexenol

Question 4

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

Question 5

What is the IUPAC name of the following compound?

A) cis-4-ethylcyclohexanol
B) trans-4-ethylcyclohexanol
C) cis-4-hydroxy-1-ethylcyclohexane
D) trans-4-hydroxy-1-ethylcyclohexane

Question 6

What is the IUPAC name of the following compound?

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

Question 7

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

Question 8

Which of the following has the highest boiling point?

A) 1-butanol
B) 2-butanol
C) tert-butyl alcohol
D) 1,4-butanediol

Question 9

What is the approximate pK_a value of ethanol?

A) -5
B) 5
C) 16
D) 25

Question 10

What is the IUPAC name of the following compound?

A) (R)-2-methyl-4-pentanol
B) (S)-2-methyl-4-pentanol
C) (R)-4-methyl-2-pentanol
D) (S)-4-methyl-2-pentanol

Question 11

What is the approximate C-O-H bond angle of an alcohol?

A) 90 $\degree$
B) 109.5 $\degree$
C) 120 $\degree$
D) 180 $\degree$

Question 12

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

Question 13

What is the IUPAC name of the following compound?

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

Question 14

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

Question 15

What is the IUPAC name of the following compound?

A) 2-cyclopentenol
B) 3-cyclopentenol
C) cyclopenten-3-ol
D) cyclopenten-2-ol

Question 16

What is the IUPAC name of the following compound?

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

Question 17

What is the IUPAC name of the following compound?

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

Question 18

What is the approximate C-C-O bond angle of ethanol?

A) 90 $\degree$
B) 109.5 $\degree$
C) 120 $\degree$
D) 180 $\degree$

Question 19

Which of the following is/are secondary (2 $\degree$ ) alcohols?

A) only 1
B) only 3
C) only 2 and 4
D) 1, 2, 3 and 4

Question 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

Question 21

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)

Question 22

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

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

Question 23

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

Question 24

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

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

Question 25

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

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

Question 26

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

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

Question 27

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

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

Question 28

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

Question 29

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

Question 30

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

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

Question 31

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

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

Question 32

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

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

Question 33

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

Question 34

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

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

Question 35

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

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

Question 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

Question 37

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

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

Question 38

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

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

Question 39

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

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

Question 40

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

Question 41

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

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

Question 42

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

Question 43

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

Question 44

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

Question 45

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

A) HCl
B) NaOH
C) H₂SO₄
D) KMnO₄

Question 46

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

Question 47

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

A) ( $\pm$ )-2-azidopentane
B) (R)-2-azidopentane
C) (S)-2-azidopentane
D) (S)-2-pentyl tosylate

Question 48

What is the IUPAC name of the following compound (shown as a Fischer projection)?

Question 49

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

A) HCl
B) NaOH
C) HIO₄
D) PCC

Question 50

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

A) HCl
B) Cl₂, light
C) SOCl₂, pyridine
D) HOCl, H₂O

Question 51

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

A) 1 = thiol; 2 = sulfone; 3 = sulfoxide
B) 1 = thiol; 2 = sulfoxide; 3 = sulfone
C) 1 = thiol; 2 = sulfinic acid; 3 = sulfonic acid
D) 1 = sulfonic acid; 2 = sulfone; 3 = sulfinic acid

Question 52

What is the IUPAC name of the following compound?

Question 53

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

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

Question 54

What is the IUPAC name of the following compound (shown as a Fischer projection)?

Question 55

What is the IUPAC name of the following compound?

Question 56

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

A) trans-2-butene, (E) CH₃CH=CHCH₃
B) butanedione, CH₃COCOCH₃
C) acetaldehyde, CH₃CHO
D) acetic acid, CH₃COOH

Question 57

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

Question 58

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

A) CrO₃
B) NaOH
C) PCC
D) HIO₄

Question 59

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

A) PCC
B) HIO₄
C) CrO₃
D) NaOH

Question 60

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

Question 61

What is the IUPAC name of the following compound (shown as a Fischer projection)?

Question 62

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

Question 63

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

Question 64

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

Question 65

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

Question 66

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

Question 67

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

Question 68

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

Question 69

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

Question 70

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

Question 71

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

Question 72

What is the IUPAC name of the following compound (shown as a Fischer projection)?

Question 73

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

Question 74

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

Question 75

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

Question 76

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

Question 77

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

Question 78

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