Deck 13: Alcohols and Phenols

Question 1

What is the IUPAC name for the following compound?

Answer 1

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

Question 2

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

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

Answer 2

IV

Question 3

What is the IUPAC name for the following compound?

Answer 3

4,5,6-tripropyl-4-decanol

Question 4

What is the IUPAC name for the following compound?

Question 5

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

Question 6

What is the IUPAC name for the following compound?

Question 7

What is the IUPAC name for the following compound?

Question 8

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

Question 9

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

Question 10

What is the IUPAC name for the following compound?

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

Question 11

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 12

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 13

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 14

What is the IUPAC name for the following compound?

Question 15

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 16

What is the IUPAC name for the following compound?

Question 17

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 18

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 19

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 20

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 21

What is the IUPAC name for the following compound?

Question 22

Predict the product for the following reaction.

Question 23

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 24

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

Question 25

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

Question 26

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 27

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 28

Predict the product for the following reaction.

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

Question 29

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 30

Provide the reagents necessary to carry out the following conversion.

Question 31

Predict the product for the following reaction.

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

Question 32

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

Question 33

Predict the product for the following reaction.

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

Question 34

What is the IUPAC name for the following compound?

Question 35

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 36

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

Question 37

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 38

Predict the product for the following reaction.

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

Question 39

Predict the major product for the following reaction.

Question 40

Predict the product for the following reaction.

Question 41

Predict the product for the following reaction.

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

Question 42

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 43

Predict the product for the following reaction.

Question 44

Provide the structure(s)of the product(s)in the following reaction sequence.

Question 45

Explain why the following reaction will not produce alcohol as product.

Question 46

Predict the product for the following reaction sequence.

Question 47

Predict the major product for the following reaction.

A)I
B)II
C)III
D)IV
E)both I and III

Question 48

Predict the product(s)for the following reaction.

Question 49

Predict the product for the following reaction.

A)
B)
C)
D)
E)

Question 50

Predict the product for the following reaction sequence.

Question 51

Predict the product(s)for the following reaction.

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

Question 52

Predict the product for the following reaction.

Question 53

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

Question 54

Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine,followed by sodium bromide.

A)trans-1-bromo-3-methylcyclopentane
B)cis-1-bromo-3-methylcyclopentane
C)1-methylcyclopentene
D)2-Methylcyclopentene
E)3-Methylcyclopentene

Question 55

Predict the major product for the following reaction.

Question 56

Predict the product for the following reaction.

Question 57

Predict the major product for the following reaction.

Question 58

Predict the product for the following reaction.

Question 59

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

Question 60

Predict the major product for the following reaction.

Question 61

Provide the structure for the final product (E),in the following reaction sequence.

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

Question 62

Provide the structure for product (A),in the following reaction sequence.

A)CH₃CH₂CH₂CH₃
B)CH₃CH₂CHDCH₃
C)CH₃CH₂CHODCH₃
D)CH₃CH₂CH₂CH₂OD
E)CH₃CH₂CH₂CH₂D

Question 63

Predict the product for the following reaction.

Question 64

Provide the structure for the final product (D),in the following reaction sequence.

Question 65

Predict the product for the following reaction.

Question 66

Provide the reagents necessary to carry out the following conversion.

A)KMnO₄/NaOH/H₂O
B)CrO₃/H₂SO₄/H₂O
C)PCC/CH₂Cl₂
D)Br₂,CCl₄
E)None of these

Question 67

Predict the product for the following reaction.

Question 68

Provide the reagents necessary to carry out the following conversion.

A)KMnO₄/NaOH/H₂O
B)CrO₃/H₂SO₄/H₂O
C)PCC/CH₂Cl₂
D)Br₂,CCl₄
E)None of these

Question 69

Predict the product for the following reaction.

Question 70

Provide the reagents necessary to carry out the following conversion.

A)KMnO₄/NaOH/H₂O
B)CrO₃/H₂SO₄/H₂O
C)H₂,Pt
D)Br₂,CCl₄
E)None of these

Question 71

Predict the product for the following reaction.