Deck 12: Alcohols and Phenols

Question 1

Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.

Answer 1

Question 2

What is the IUPAC name for the following compound?

A) 2-methyl-5-bromocyclohexanol
B) 3-bromo-2-methylcyclohexanol
C) 1-bromo-4-methylcyclohexanol
D) 4-bromo-6-methylcyclohexanol
E) 4-bromo-2-methylcyclohexanol

Answer 2

4-bromo-2-methylcyclohexanol

Question 3

What is the IUPAC name for the following compound?

Answer 3

7-ethyl-8-methyl-4-nonanol

Question 4

What is the IUPAC name for the following compound?

Question 5

What is the IUPAC name for t-butyl alcohol?

A) 1-butanol
B) 2-methyl-1-propanol
C) 2-methyl-2-propanol
D) 2-butanol
E) 1,1-dimethyl-1-ethanol

Question 6

Provide the structure for 5-chloro-2-propyl-1-heptanol.

Question 7

What is the correct structure for 1-chloro-3-ethyl-2-pentanol?

A) I
B) II
C) III
D) IV
E) None of these

Question 8

What is the IUPAC name for the following compound?

A) (R)-3-hexyn-2-ol
B) (S)-3-hexyn-2-ol
C) (R)-2-hexyn-4-ol
D) (S)-2-hexyn-4-ol
E) (S)-2-hydroxy-3-hexyne

Question 9

What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?

A) I
B) II
C) III
D) IV
E) V

Question 10

What is the IUPAC name for the following compound?

A) 4-isopropyl-3,4-dimethyl-2-butanol
B) 2,3,4-trimethyl-4-pentanol
C) 1,1,2,3-tetramethyl-4-pentanol
D) 3,4,5-trimethyl-2-hexanol
E) 3,4,5,5-tetramethyl-2-pentanol

Question 11

What is the IUPAC name for the following compound?

A) 3-methyl-4-ethyl-3-hexen-6-ol
B) 4-ethyl-3-methyl-3,6-hexenol
C) 3-ethyl-4-methyl-3-hexen-1-ol
D) 3-methyl-4-(2-hydroxyethyl)-3-hexene
E) 3-(2-hydroxyethyl)-3-methyl-3-hexene

Question 12

Give the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol.

Question 13

What is the IUPAC name for the following compound?

A) 4-penten-2-methyl-2-ol
B) 4-methyl-1-penten-2-ol
C) 2-methyl-4-penten-2-ol
D) 4-methyl-1-penten-4-ol
E) 4-hydroxy-4-methyl-1-pentene

Question 14

What is the IUPAC name for the following compound?

A) 1,1,1-triethylmethanol
B) 1,1-diethyl-1-propanol
C) 2-ethyl-3-pentanol
D) 3-ethyl-3-pentanol
E) t-heptanol

Question 15

What is the IUPAC name for isobutyl alcohol?

A) 2-methyl-1-propanol
B) 2-methyl-1-butanol
C) 1-methyl-1-propanol
D) 1,1-dimethyl-1-ethanol
E) 3-methyl-1-propanol

Question 16

What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?

A) I
B) II
C) III
D) IV
E) V

Question 17

What is the IUPAC name for the following compound?

Question 18

What is the IUPAC name for the following compound?

A) 1-isopropyl-4-cyclopentanol
B) 3-isopropylcyclopentanol
C) 1-isopropyl-3-cyclopentanol
D) 1-isopropyl-4-hydroxycyclopentane
E) None of these

Question 19

What is the IUPAC name for the following compound?

Question 20

What is the IUPAC name for the following compound?

Question 21

What is the IUPAC name for the following compound?

Question 22

What is the IUPAC name for the following compound?

Question 23

What is the IUPAC name for the following compound?

A) cis-1,2-cyclopentanediol
B) meso-1,2-cyclopentanediol
C) (1R,2R)-1,2-cyclopentanediol
D) (1R,2S)-1,2-cyclopentanediol
E) (1S,2S)-1,2-cyclopentanediol

Question 24

Identify the alcohol in alcoholic drinks.

A) methanol
B) 2-propanol
C) ethanol
D) 1-butanol
E) 1-propanol

Question 25

Identify wood alcohol.

A) methanol
B) 2-propanol
C) ethanol
D) 1-butanol
E) 1-propanol

Question 26

Identify rubbing alcohol.

A) methanol
B) 2-propanol
C) ethanol
D) 1-butanol
E) 1-propanol

Question 27

Rank the following alcohols in decreasing order of acidity. Explain your answer.

A) II > I > III
B)I > II > III
C)I > III > II
D)III > I > II
E) III > II > I

Question 28

What is the IUPAC name for the following compound? HOCH₂CH₂CH₂OH

A) 1,2-butanediol
B) isopropyl alcohol
C) 1-propanol
D) 1,3-propanediol
E) 1,2-ethanediol

Question 29

Explain why cyclohexanol has a pK_a of 18 and phenol has a pK_a of 10. Use structural drawings to explain your reasoning.

Question 30

What is the correct structure for 2-methylphenol?

A) I
B) II
C) III
D) IV
E) V

Question 31

What is the IUPAC name for the following compound?

A) 3,4-dibromophenol
B) 2,4-dibromophenol
C) 2,5-dibromophenol
D) 3,6-dibromophenol
E) 2,6-dibromophenol

Question 32

What is the IUPAC name for the following compound?

Question 33

Identify the type of bonding between molecules of alcohol.

A) ion-ion
B) van der Waals forces
C) hydrogen bonding
D) ion-dipole
E) London dispersion

Question 34

What is the correct structure for 2-bromo-5-isopropylphenol?

A) I
B) II
C) III
D) IV
E) V

Question 35

Rank the following alcohols in decreasing order of acidity.

A) II > I > III
B) I > II > III
C) I > III > II
D) III > I > II
E) III > II > I

Question 36

What is the IUPAC name for the following compound?

Question 37

Provide the structure for (2R,3S) -2-bromo-1,3-pentanediol.

Question 38

Identify grain alcohol.

A) methanol
B) 2-propanol
C) ethanol
D) 1-butanol
E) 1-propanol

Question 39

What is the IUPAC name for the following compound?

Question 40

Which one of the following alcohols is most acidic?

A) I
B) II
C) III
D) IV

Question 41

Identify the characteristics of the acid-catalyzed hydration of an alkene.

A) Markovnikov, with rearrangement possible
B) Markovnikov, with no rearrangement possible
C) anti-Markovnikov, with rearrangement possible
D) anti-Markovnikov, with no rearrangement possible

Question 42

Predict the product(s) for the following reaction.

Question 43

Provide the reagents necessary to carry out the following conversion.

Question 44

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) None of these

Question 45

Predict the product(s) for the following reaction.

Question 46

What are the oxidation states of carbon atoms I and II in the following reaction?

A) I. +1, II. +2
B) I. +2, II. +2
C) I. +1, II. +3
D) I. +3, II. +2
E) I. +2, II. +1

Question 47

For the following conversion, identify if the starting material has been oxidized, reduced or neither. Explain your answer.

Question 48

For the following conversion, identify if the starting material has been oxidized, reduced or neither. Explain your answer.

Question 49

Identify the characteristics of the hydroboration-oxidation of an alkene.

A) Markovnikov, with rearrangement possible
B) Markovnikov, with no rearrangement possible
C) anti-Markovnikov, with rearrangement possible
D) anti-Markovnikov, with no rearrangement possible

Question 50

Predict the major product for the following reaction.

Question 51

Provide the reagents necessary to carry out the following conversion.

Question 52

Identify the characteristics of the oxymercuration-demercuration of an alkene.

A) Markovnikov, with rearrangement possible
B) Markovnikov, with no rearrangement possible
C) anti-Markovnikov, with rearrangement possible
D) anti-Markovnikov, with no rearrangement possible

Question 53

Provide the reagents necessary to carry out the following conversion.

A) NaOH/H₂O
B) 1. NaOCH₃, 2. H₃O⁺
C) 1. (CH₃)₃COK, 2. BH₃•THF, 3. H₂O₂/NaOH/H₂O
D) 1. (CH₃)₃COK, 2. H₃O⁺
E) B & D

Question 54

Provide the reagents necessary to carry out the following conversion.

Question 55

Predict the product for the following reaction.

Question 56

Rank the following alcohols in decreasing order of acidity.

A) II > I > III
B) I > II > III
C) I > III > II
D) III > I > II
E) III > II > I

Question 57

Predict the product(s) for the following reaction.

A) I
B) II
C) III
D) IV
E) None of these

Question 58

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 59

For the following conversion, identify if the starting material has been oxidized, reduced or neither.

Question 60

What are the oxidation states of carbon atoms I and II in the following compound?

A) I. +1, II. +2
B) I. +2, II. +2
C) I. +1, II. +3
D) I. +3, II. +2
E) I. +2, II. +1

Question 61

Predict the product(s) for the following reaction.

Question 62

Predict the product for the following reaction.

Question 63

Provide the reagents necessary to carry out the following conversion.

A) KMnO₄, NaOH,H₂O
B) KMnO₄, H₃O⁺, 75^oC
C) H₂SO₄, heat
D) 1. mCPBA 2. H₃O⁺
E) none of these

Question 64

Predict the product(s) for the following reaction.

A) I
B) II
C) III
D) IV
E) none of these

Question 65

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV

Question 66

Provide the reagents necessary to carry out the following conversion.

A) KMnO₄, NaOH,H₂O,cold
B) KMnO₄, H₃O⁺, 75^oC
C) H₂SO₄, heat
D) 1. mCPBA 2. H₃O⁺
E) none of these

Question 67

Predict the product for the following reaction.

Question 68

Provide the reagent(s) necessary to carry out the following conversion.

Question 69

For the following conversion, identify if the starting material has been oxidized, reduced or neither.

A) reduced
B) oxidized
C) neither
D) A & B

Question 70

For the following conversion, identify if the starting material has been oxidized, reduced or neither.

A) reduced
B) oxidized
C) neither
D) A & B

Question 71

Predict the product(s) for the following reaction sequence.

A) I
B) II
C) III
D) Both I & II
E) None of these

Question 72

Predict the product for the following reaction.

Question 73

Predict the product for the following reaction.

Question 74

Provide the reactant (A) for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 75

Predict the product for the following reaction sequence.

Question 76

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 77

Provide the structure of each product (A-D) in the following reaction sequence.

Question 78

Provide the reagent(s) necessary to carry out the following conversion.

Question 79

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV

Question 80

Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH₄ followed by water?

A) I
B) II
C) III
D) IV
E) V