Deck 11: Reactions of Alcohols

Question 1

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

Answer 1

No reaction. Tertiary alcohols are not oxidized by PCC.

Question 2

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 2

CO₂

Question 3

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

Answer 3

(CH₃)₃CCH₂COH

Question 4

What is the major organic product when n-butanol reacts with hydrochloric acid?

Question 5

Which alcohol reacts most rapidly with the Lucas reagent?

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

Question 6

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

A) oxidation
B) reduction
C) neither

Question 7

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

A) Cl₂
B) KMnO₄
C) O₂
D) KCl
E) H₂O₂

Question 8

The oxidation of a secondary alcohol with NaOCl in acetic acid proceeds through the reaction of the alcohol with the reactive intermediate ClOH₂⁺. Write a mechanism that shows how isopropyl alcohol is oxidized to acetone (CH₃COCH₃) using ClOH₂⁺ in acetic acid (CH₃COOH).

Question 9

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

A) oxidation
B) reduction
C) neither

Question 10

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

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

Provide the major organic product of the following reaction.

Question 13

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

Question 14

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 15

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

Question 16

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

Question 17

What is the product of the reaction shown below?

A)
B)
C)
D) No reaction takes place

Question 18

Provide the major organic product of the following reaction.

Question 19

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

Question 20

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

Question 21

Provide the major organic product of the following.

Question 22

Provide the major organic product of the following reaction.

Question 23

Complete the following reaction by filling in the necessary reagents.

Question 24

What series of synthetic steps could be used to prepare hexan-3-ol from propan-1-ol?
1) PCC
2) CH₃CH₂CH₂MgBr
3) H₃O⁺
or

Question 25

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

Question 26

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

Question 27

Which of the following oxidants will convert a primary alcohol to an aldehyde?
1) sodium dichromate /sulfuric acid 3) pyridinium chlorochromate
2) copper oxide 4) dimethylsulfoxide, oxalyl chloride

A) 3 & 4
B) 2, 3, & 4
C) 3
D) 1, 2, 3, & 4
E) none of the above

Question 28

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

Question 29

What is the product of the following reaction?

Question 30

Provide the name of the major organic product that results when trans-4-methylcyclohexanol is treated with Lucas reagent.

Question 31

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

Question 32

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

Question 33

Provide the major organic product of the reaction shown.

Question 34

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

Question 35

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

Question 36

Provide the major organic product of the reaction shown.

Question 37

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

Question 38

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

Question 39

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

Question 40

Which reagent could be used to perform the following reaction?

A) NaOCl/TEMPO
B) Swern Oxidation
C) DMP (periodane) reagent
D) All reagents will work

Question 41

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 42

Provide the major organic product of the reaction shown.

Question 43

Provide the major organic product of the following.

Question 44

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

Question 45

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

Question 46

Provide the major organic product of the reaction shown.

Question 47

Provide the necessary reagents for the following conversion.

Question 48

Provide the major organic product of the following reaction.

Question 49

Provide the major organic product of the following.

Question 50

What is the final product of the reaction sequence shown below, making sure to include stereochemistry as appropriate.

Question 51

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

Question 52

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 53

Which of the following reactions or series of reactions would reduce 3-methylbutan-2-ol into 2-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 54

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 55

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

Question 56

Provide the major organic product of the following.

Question 57

Why are alcohols unreactive toward nucleophilic substitution reactions?

Question 58

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

Question 59

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

Question 60

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

Question 61

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

Question 62

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 63

What series of synthetic steps could be used to carry out the transformation shown below?
1) HBr, ROOR
2) NaCN
or

Question 64

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 65

What is the major organic product of the following reaction?

A)
B)
C)
D) Both A and B

Question 66

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

Question 67

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

A) I₂
B) HI
C) NaI
D) P / I₂

Question 68

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 69

Draw a mechanism for the following reaction.

Question 70

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

Question 71

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

Question 72

Provide the major organic product of the reaction shown.

Question 73

Provide the major organic product of the reaction shown.

Question 74

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

Question 75

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

Question 76

Provide the major organic product of the following.

Question 77

How could tell a sample of n-butanol from tert-butanol?

Question 78

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

Question 79

Provide the major organic product of the reaction shown.

Question 80

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