Deck 13: Alcohols and Phenols

Question 1

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

Answer 1

(S)-3-hexyn-2-ol

Question 2

What is the IUPAC name for the following compound?

Answer 2

4,5,6-tripropyl-4-decanol

Question 3

What is the IUPAC name for the following compound?

Answer 3

(R)-3-ethyl-2-methyl-3-heptanol

Question 4

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 5

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 6

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 7

Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol?

Question 8

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

Question 9

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 10

What is the IUPAC name for the following compound?

Question 11

What is the IUPAC name for the following compound?

Question 12

What is the IUPAC name for the following compound?

Question 13

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

Question 14

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 15

What is the IUPAC name for the following compound?

Question 16

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

Question 17

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

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

Question 18

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 19

What is the IUPAC name for the following compound?

Question 20

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 21

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

Question 22

Predict the product for the following reaction.

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

Question 23

Provide the reagents necessary to carry out the following conversion.

Question 24

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

Question 25

What is the IUPAC name for the following compound?

Question 26

Provide the reagents necessary to carry out the following conversion.

Question 27

What is the IUPAC name for the following compound?

Question 28

Predict the major product for the following reaction.

Question 29

What is the oxidation state of the 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 30

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

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

Question 31

Predict the product for the following reaction.

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

Question 32

Predict the product(s) for the following reaction.

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

Question 33

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 34

What is the IUPAC name for the following compound? HOCH₂CH₂CH₂OH

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

Question 35

What is the IUPAC name for the following compound?

Question 36

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 37

Provide the reagents necessary to carry out the following conversion.

Question 38

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

Question 39

What is the oxidation state of the 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 40

What is the correct structure for 2-methylphenol?

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

Question 41

Predict the product for the following reaction sequence.

Question 42

Predict the product for the following reaction sequence.

Question 43

Predict the product for the following reaction.

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

Question 44

Predict the product for the following reaction.

Question 45

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 46

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

Question 47

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 48

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

Question 49

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

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

Question 50

Provide the reactant (A) for the following reaction

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

Question 51

Predict the product for the following reaction.

Question 52

Predict the product for the following reaction.

Question 53

Predict the product for the following reaction.

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

Question 54

Predict the product for the following reaction.

Question 55

Predict the product(s) for the following reaction.

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

Question 56

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

Question 57

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

Question 58

Predict the product(s) for the following reaction.

Question 59

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

Question 60

Predict the product for the following reaction.

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

Question 61

Predict the product for the following reaction.

Question 62

Predict the product for the following reaction.

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

Question 63

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

Question 64

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

Question 65

Provide the reagents necessary to convert 3-methyl-2-butanol to 2-bromo-3-methylbutane.

A) conc. HBr
B) Br₂
C) NaBr, H₂SO₄
D) PBr₃
E) HBr, peroxide

Question 66

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

Question 67

Predict the product for the following reaction.

Question 68

Which of the following could be used to synthesize 1-bromopentane?

A) CH₃CH₂CH₂CH=CH₂ + HBr $\rightarrow$
B) CH₃CH₂CH₂CH₂CH₂OH + PBr₃ $\rightarrow$
C) CH₃CH₂CH₂CH₂CH₂OH + NaBr $\rightarrow$
D) CH₃CH₂CH₂CH₂CH₂OH + Br₂ $\rightarrow$
E) CH₃CH₂CH₂CH=CH₂ + Br₂ $\rightarrow$

Question 69

Using Grignard reaction, show how you could prepare the following alcohol.

Question 70

Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product.

Question 71

Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction.

Question 72

Predict the structure of each product(A-D) for the following reaction sequence.

Question 73

Using Grignard reaction, show how you could prepare the following alcohol.

Question 74

Predict the product for the following reaction.

Question 75

Predict the product for the following reaction sequence.

A) 2,4-heptanediol
B) 1,4-heptanediol
C) 2,5-octanediol
D) 1,5-octanediol
E) none of these

Question 76

Predict the product for the following reaction.

Question 77

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

Question 78

Predict the product for the following reaction.

Question 79

Provide the reagents necessary to carry out the following conversion.

Question 80

Using Grignard reaction, show how you could prepare the following alcohol.