Deck 11: Reactions of Alcohols

Question 1

Which of the following compounds has carbon in the highest oxidation state?

A) CO₂
B) CH₃C(O)CH₃
C) CH₃CH₂OH
D) CH₃C(OCH₂CH₃)₃

Answer 1

CO₂

Question 2

Which of the following alcohols will give a positive chromic acid test?

A) tert-butanol
B) cyclohexanol
C) pentan-3-ol
D) both A and B
E) both B and C

Answer 2

both B and C

Question 3

Provide the structure of the major organic product in the reaction below.

Answer 3

No reaction. Tertiary alcohols are not oxidized by PCC.

Question 4

Provide the major organic product of the following reaction.

Question 5

Circle all carbon centers that are at the same oxidation state as a carboxylic acid.

Question 6

Provide the structure of the major organic product in the reaction below.

Question 7

Which alcohol reacts most rapidly with the Lucas reagent?

A) benzyl alcohol
B) methanol
C) 2-propanol
D) isobutanol

Question 8

Describe the composition of the Jones reagent.

Question 9

Provide the structure of the major organic product in the reaction below.

Question 10

Classify the reaction below as an oxidation, a reduction, or neither.
PhCO₂H → PhCH₂OH

A) oxidation
B) reduction
C) neither

Question 11

Which of the following reagents is the best choice for oxidizing a primary alcohol to an aldehyde?

A) H₂CrO₄
B) pyridinium chlorochromate
C) Na₂Cr₂O₇, H₂SO₄
D) KMnO₄
E) LiAlH₄

Question 12

In the chromic acid oxidation of alcohols, the chromium is:

A) oxidized from Cr⁺³ to Cr⁺⁶.
B) reduced from Cr⁺⁶ to Cr⁺³.
C) oxidized from Cr⁺⁶ to Cr⁺³.
D) reduced from Cr⁺³ to Cr⁺⁶.
E) none of the above

Question 13

Provide the structure of the major organic product in the reaction below.
(CH₃)₃CCH₂CH₂OH $\rightarrow$

Question 14

Classify the reaction below as an oxidation, a reduction, or neither.
cis-pent-2-ene → pentane

A) oxidation
B) reduction
C) neither

Question 15

Provide the major organic product of the following reaction.

Question 16

What series of synthetic steps could be used to carry out the transformation shown below?

Question 17

Provide the structure of the major organic product in the reaction below.

Question 18

Which of the following reagents is not typically viewed as an oxidizing agent?

A) Cl₂
B) KMnO₄
C) O₂
D) KCl
E) H₂O₂

Question 19

Chromic acid oxidations are believed to proceed through a chromate ester intermediate. In the oxidation of propran-1-ol, provide the structure of this ester and give the mechanism for its conversion to the intermediate aldehyde.

Question 20

Classify the reaction below as an oxidation, a reduction, or neither. (CH₃)₂CHCH₂OH → (CH₃)₂CHCHO

A) oxidation
B) reduction
C) neither

Question 21

Provide the major organic product of the following reaction.

Question 22

Which of the following catalysts is commonly used in industry to dehydrogenate alcohols?

A) CuO
B) Na
C) NaBH₄
D) (CH₃)₂S
E) Zn

Question 23

Provide the structure of the major organic product that results when 3-hexanol is treated with sodium dichromate.

Question 24

Provide the major organic product of the following.

Question 25

Provide the major organic product of the following.

Question 26

Name the product which results when 1-methylcyclohexanol is treated with PCC.

Question 27

What series of synthetic steps could be used to carry out the transformation shown below?

Question 28

What series of synthetic steps could be used to prepare hexan-3-ol from propan-1-ol?

Question 29

Provide the major organic product of the following.

Question 30

Provide the structure of the major organic product in the reaction below.

Question 31

What series of synthetic steps could be used to prepare (CH₃)₂CHCHO from (CH₃)₃CH?

Question 32

What series of synthetic steps could be used to prepare PhCH(OH)CH₂CH₃ from PhCH₂OH?

Question 33

What series of synthetic steps could be used to prepare 1-methylcyclohexanol from cyclohexene?

Question 34

Provide the structure of the major organic product that results when 1-octanol is treated with pyridinium chlorochromate.

Question 35

Provide the major organic product of the reaction shown.

Question 36

What series of synthetic steps could be used to carry out the transformation shown below?

Question 37

Provide the name of the major organic product that results when $\underline{\text{ trans }}$ -4-methylcyclohexanol is treated with Lucas reagent.

Question 38

Provide the major organic product of the reaction shown.

Question 39

Complete the following reaction by filling in the necessary reagents.

Question 40

Provide the reagents necessary to carry out the multistep synthesis shown below.

Question 41

Provide the structure of the major organic product which results when ethyl tosylate is reacted with potassium t-butoxide.

Question 42

Provide the major organic product of the following.

Question 43

How can the electrophilicity of hydroxyls be increased? Suggest several specific ways.

Question 44

Provide the name of the major organic product that results when (R)-2-butyl tosylate is treated with sodium iodide.

Question 45

Why are alcohols unreactive toward nucleophilic substitution reactions?

Question 46

Provide the major organic product of the following reaction.

Question 47

Provide the structure of the major organic product in the reaction below.
(CH₃)₂CHCH₂OH

Question 48

The enzyme, alcohol dehydrogenase, which is produced by the liver, converts ethanol to ________, a normal body metabolite.

Question 49

Provide the structure of the major organic product in the reaction below.
PhCH₂CH₂OH →

Question 50

Provide the structure of the major organic product in the reaction below.

Question 51

Provide the major organic product of the reaction shown.

Question 52

Which of the following reactions or series of reactions would reduce 3-metylbutan-2-ol into 3-methylbutane?

A) 1. TsCl/pyridine
2. conc. KMnO₄
B) 1. NaOCH₃
2.. H₂SO₄/heat
C) 1. pyridinium chlorochromate
2. ZnCl₂/HCl
D) 1. ZnCl₂/HCl
2. t-butoxide/t-butanol
E) 1. TsCl/pyridine
2. LiAlH₄

Question 53

What compound is produced when (R)-pentan-2-ol is treated with TsCl followed by NaI?

A) sodium (R)-pent-3-oxide
B) sodium (S)-pent-2-oxide
C) (R)-2-iodopentane
D) (S)-2-iodopentane
E) none of the above

Question 54

Provide the major organic product of the reaction shown.

Question 55

When (R)-butan-2-ol is treated with TsCl in pyridine, the product formed is:

A) a single enantiomer.
B) a racemic mixture.
C) a mixture of diastereomers.
D) an achial compound.
E) none of the above

Question 56

Provide the major organic product of the following.

Question 57

Provide the necessary reagents for the following conversion.

Question 58

Draw the tosylate ion and explain why it is a particularly good leaving group.

Question 59

Poisonings by methanol and ethylene glycol are relatively common. How are these poisonings treated clinically?

Question 60

Provide the name of the major organic product that results when cyclopentanol is subjected to the following sequence of reactions: 1. TsCl, pyridine; 2. LiAlH₄.

Question 61

Provide the major organic product of the reaction shown.

Question 62

Provide the major organic product of the following.

Question 63

Which reagent would be best suited to induce the following transformation?

A) I₂
B) HI
C) NaI
D) P / I₂

Question 64

What series of synthetic steps could be used to carry out the transformation shown below?

Question 65

Provide the major organic product of the following.

Question 66

What compound results when 1-butanol is treated with P/I₂?

A) CH₃CH₂CH₂CH₂I
B) racemic CH₃CH₂CHICH₃
C) CH₃CH₂CH₂CH₂OP(OH)₂
D) CH₃CH₂CH₂CH₂PI₂
E) Primary alcohols don't react with P/I₂.

Question 67

Provide the structure of the major organic product that results when 4-methyl-1-pentanol is treated with PBr₃.

Question 68

Provide the structure of the major organic product in the reaction below.

Question 69

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.
(CH₃)₃CCH₂OH + HBr →

Question 70

Provide the structure of the major organic product in the reaction below.
(CH₃)₂CHCH₂OH

Question 71

Provide the structure of the major organic product in the reaction below.

Question 72

Identify the sequence of reactions that successfully completes the following transformation.

A) 1. BH₃ 2. H₂O₂ / NaOH 3. P, I₂
B) HI / hν
C) 1. HBr / hν 2. NaI, acetone
D) A and C
E) all of the above

Question 73

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.
CH₃(CH₂)₆CH₂OH + HBr →

Question 74

What series of synthetic steps could be used to prepare 1-bromopentane from 1-bromopropane?

Question 75

Provide the major organic product of the reaction shown.

Question 76

Through what basic mechanism is 1-methylcyclohexanol converted to 1-bromo-1-methylcyclohexane upon treatment with HBr?

A) S_N1
B) S_N2
C) E1
D) E2
E) radical chain

Question 77

Provide the major organic product of the reaction shown.

Question 78

It is necessary to add ZnCl₂ to promote the reaction of HCl with some alcohols while these same alcohols react with HBr quite readily. Explain.

Question 79

Provide the structure of the major organic product in the reaction below.

Question 80

Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl₂)?

A) (CH₃)₃COH
B) CH₃CH₂CH₂CH₂OH
C) CH₃CH(OH)CH₂CH₃
D) (CH₃)₂CHCH₂OH