Deck 10: Alcohols

Question 1

What is the major organic product obtained from the reaction of 2,2-dimethyl-1-propanol aqueous HBr at reflux?

A) 1-bromo-2,2-dimethylpropane
B) 1-bromo-2-methylbutane
C) 2-bromo-2-methylbutane
D) 3-bromo-2-methylbutane

Answer 1

2-bromo-2-methylbutane

Question 2

What is the IUPAC name of the following compound?

A) (R)-2-methyl-4-pentanol
B) (S)-2-methyl-4-pentanol
C) (R)-4-methyl-2-pentanol
D) (S)-4-methyl-2-pentanol

Answer 2

(R)-4-methyl-2-pentanol

Question 3

What is the approximate C−C−O bond angle of ethanol?

A) 90°
B) 109.5°
C) 120°
D) 180°

Answer 3

109.5°

Question 4

What is the IUPAC name of the following compound?

A) (R)-2,2-dimethyl-3-pentanol
B) (S)-2,2-dimethyl-3-pentanol
C) 1-tert-butyl-1-propanol
D) (S)-4,4-dimethyl-3-pentanol

Question 5

What is the IUPAC name of the following compound?

A) cis-4-ethylcyclohexanol
B) trans-4-ethylcyclohexanol
C) cis-4-hydroxy-1-ethylcyclohexane
D) trans-4-hydroxy-1-ethylcyclohexane

Question 6

What is the IUPAC name of the following compound?

A) (E)-5-methyl-2-hexen-5-ol
B) (Z)-5-methyl-2-hexen-5-ol
C) (E)-2-methyl-4-hexen-2-ol
D) (Z)-2-methyl-4-hexen-2-ol

Question 7

Which of the following has the highest boiling point?

A) pentane
B) methyl propyl ether
C) diethyl ether
D) 1-butanol

Question 8

What is the IUPAC name of the following compound?

A) cyclohexen-3-ol
B) cyclohexen-2-ol
C) 2-cyclohexenol
D) 3-cyclohexenol

Question 9

What is the IUPAC name of the following compound?

A) cis-4-isopropylcyclohexanol
B) trans-4-isopropylcyclohexanol
C) cis-4-hydroxy-1-isopropylcyclohexane
D) trans-4-hydroxy-1-isopropylcyclohexane

Question 10

What is the IUPAC name of the following compound?

A) 4−methyl-4-penten-1-ol
B) 2-methyl-1-penten-5-ol
C) 5-hydroxy-2-methyl-1-pentene
D) 4-methyl-5-penten-1-ol

Question 11

What is the approximate pK_a value of ethanol?

A) −5
B) 5
C) 16
D) 25

Question 12

What is the IUPAC name of the following compound?

A) (E)-2-methyl-3-penten-2-ol
B) (Z)-2-methyl-3-penten-2-ol
C) (E)-4-methyl-2-penten-4-ol
D) (Z)-2-methyl-4-penten-2-ol

Question 13

Which of the following best describes the reaction of sodium metal with methanol to give hydrogen and sodium methoxide?

A) Lewis acid-base
B) Brønsted-Lowry acid-base
C) electrophile-nucleophile
D) oxidation-reduction

Question 14

What is the IUPAC name of the following compound?

A) 2-cyclopentenol
B) 3-cyclopentenol
C) cyclopenten-3-ol
D) cyclopenten-2-ol

Question 15

What is the IUPAC name of the following compound?

A) 3-methyl-1-penten-4-ol
B) 3-methyl-4-penten-2-ol
C) 1,2-dimethyl-2-propan-1-ol
D) 2,3-dimethyl-1-propan-3-ol

Question 16

What is the major organic product obtained from the reaction of 1-butanol with aqueous HBr at reflux?

A) 1-bromobutane
B) 2-bromobutane
C) 2-bromo-1-butanol
D) 1-butene

Question 17

Which of the following is/are secondary (2°) alcohols?

A) only 1
B) only 3
C) only 2 and 4
D) 1, 2, 3 and 4

Question 18

What is the approximate C−O−H bond angle of an alcohol?

A) 90°
B) 109.5°
C) 120°
D) 180°

Question 19

Which of the following is/are primary (1°) alcohols?

A) only 1
B) only 3
C) only 1 and 3
D) only 2, 3, and 4

Question 20

Which of the following has the highest boiling point?

A) 1-butanol
B) 2-butanol
C) tert-butyl alcohol
D) 1,4-butanediol

Question 21

What type of reactive intermediate is formed in the reaction of 2-methyl-2-hexanol with HBr to give 2-bromo-2-methylhexane?

A) an alkoxide
B) a tertiary cation
C) a tertiary radical
D) a tertiary anion

Question 22

What is the major organic product obtained upon heating a mixture of 2-methylcyclopentanol and 85% H₃PO₄?

A) 1-methylcyclopentene
B) 3-methylcyclopentene
C) 4-methylcyclopentene
D) methylenecyclopentene

Question 23

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 24

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 25

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 26

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 27

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 28

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 29

What is the major organic product obtained upon heating a mixture of 3,3-dimethyl-2-butanol, (CH₃)₃CCH(OH)CH₃, with sulfuric acid?

A) 3,3-dimethyl-1-butene
B) 2,3-dimethyl-1-butene
C) 2,3-dimethyl-2-butene
D) tert-butyl alcohol

Question 30

Which of the following alcohols undergoes the most rapid dehydration upon treatment with H₂SO₄ to give an alkene?

A) 1
B) 2
C) 3
D) 4

Question 31

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 32

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 33

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 34

What is the major organic product obtained upon heating a mixture of 2-butanol and 85% H₃PO₄?

A) 1-butene
B) cis-2-butene
C) trans-2-butene
D) 2-methylpropene (isobutylene)

Question 35

Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?

A) 1
B) 2
C) 3
D) 4

Question 36

Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide?

A) methanol
B) ethanol
C) 2-propanol
D) 2-methyl-2-propanol

Question 37

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 38

Which of the following alcohols undergoes the most rapid dehydration upon treatment with H₂SO₄ to give an alkene?

A) methanol
B) ethanol
C) 2-propanol
D) 2-methyl-2-propanol

Question 39

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 40

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 41

What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H₂SO₄ to give methylpropene?

A) tert-butyl cation
B) tert-butyl anion
C) tert-butyl radical
D) tert-butoxide

Question 42

Consider following structures. Only structure III represents a secondary alcohol.

Question 43

What is the major organic product obtained from the following sequence of reactions?

A) (±)-2-azidopentane
B) (R)-2-azidopentane
C) (S)-2-azidopentane
D) (S)-2-pentyl tosylate

Question 44

What is the correct assignment of the names of the following functional groups?

A) 1 = thiol; 2 = sulfone; 3 = sulfoxide
B) 1 = thiol; 2 = sulfoxide; 3 = sulfone
C) 1 = thiol; 2 = sulfinic acid; 3 = sulfonic acid
D) 1 = sulfonic acid; 2 = sulfone; 3 = sulfinic acid

Question 45

The following substance would be correctly name as 2-pentanthiol. $\quad$$\text { SH }$
$\quad$$\quad$ |
$\mathrm{CH}_{3} \mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$

Question 46

(CH₃)₃CO^- Na⁺ would be formed by the reaction of sodium metal and 1-butanol.

Question 47

What is the best choice of reagent to achieve the following transformation?

A) HCl
B) Cl₂, light
C) SOCl₂, pyridine
D) HOCl, H₂O

Question 48

What is the best choice of reagent to perform the following transformation?

A) HCl
B) NaOH
C) H₂SO₄
D) KMnO₄

Question 49

What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with HCl to give tert-butyl chloride?

A) tert-butyl radical
B) tert-butyl anion
C) tert-butyl cation
D) tert-butoxide

Question 50

What is the best choice of reagent to perform the following transformation?

A) HCl
B) NaOH
C) HIO₄
D) PCC

Question 51

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 52

What is the major organic product obtained from the following reaction?

A) trans-2-butene, (E) CH₃CH=CHCH₃
B) butanedione, CH₃COCOCH₃
C) acetaldehyde, CH₃CHO
D) acetic acid, CH₃COOH

Question 53

What is the major organic product obtained from the following reaction?

A) 1,6-hexanediol, HO(CH₂)₆OH
B) hexanedial, OHC(CH₂)₄CHO
C) hexanedioic acid, HO₂C(CH₂)₄COOH
D) cyclohexene

Question 54

What is the major organic product obtained from the following reaction?

A) 1-butene, CH₃CH₂CH=CH₂
B) butanal, CH₃CH₂CH₂CHO
C) butanone, CH₃CH₂COCH₃
D) butanoic acid, CH₃CH₂CH₂COOH

Question 55

What is the best choice of reagent to perform the following transformation?

A) PCC
B) HIO₄
C) CrO₃
D) NaOH

Question 56

What is the major organic product obtained from the following reaction?

A) 1-butene, CH₃CH₂CH=CH₂
B) butanal, CH₃CH₂CH₂CHO
C) butanone, CH₃CH₂COCH₃
D) butanoic acid, CH₃CH₂CH₂COOH

Question 57

What is the major organic product obtained from the following sequence of reactions?

A) 3-methyl-1-butene
B) 2-iodo-2-methylbutane
C) 1-iodo-3-methylbutane
D) 1-chloro-3-methylbutane

Question 58

What is the best choice of reagent to achieve the following transformation?

A) CrO₃
B) NaOH
C) PCC
D) HIO₄

Question 59

What is the major organic product obtained from the following reaction?

A) 1
B) 2
C) 3
D) 4

Question 60

The following substance would be named as 3-pentyn-1-ol. $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{OH}$

Question 61

Consider the following species. This substance is a _______conjugate base than the substance shown below.

Question 62

To answer the following question, consider the reaction below:
Provide the complete IUPAC name for the starting material in this reaction.

Question 63

What is the IUPAC name of the following compound?

Question 64

Of the following compounds, 3 would have the highest boiling point. 1. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{3}$$\quad$$\quad$ 2. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$$\quad$$\quad$$\quad$ 3. $\begin{array}{c}\mathrm{CH}_{3} \mathrm{CHCH}_{3}\\|\\\mathrm{OH}\end{array}$

Question 65

(CH₃)₃COH would react faster than (CH₃)₂CHCH₂OH under S_N1 conditions.

Question 66

What is the major organic product obtained from the following reaction?

Question 67

The rate-determining step in the following reaction is protonation of the alcohol. $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OH}+\mathrm{HBr} \longrightarrow\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{Br}+\mathrm{H}_{2} \mathrm{O}$ ?

Question 68

Reaction with Na, NaH, or NaOH can be used to irreversibly accomplish the following reaction. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{ONa}^{+}$

Question 69

Including stereoisomers, the number alkene isomers produced by the acid-catalyzed dehydration of 3-methyl-3-hexanol is _____.

Question 70

What is the IUPAC name of the following compound?

Question 71

The starting material would be classified as a __________ alcohol.

Question 72

The mechanism of this reaction would be classified as ______.

Question 73

When a secondary (2°) alcohol is treated with Jones reagent the product of the reaction is a ketone.

Question 74

What is the IUPAC name of the following compound (shown as a Fischer projection)?

Question 75

The rate-determining step in the following reaction is displacement of water from the protonated alcohol by the bromide ion. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{HBr} \stackrel{\text { heat }}{\longrightarrow} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{H}_{2} \mathrm{O}$

Question 76

The pK_a of CH₃CH₂CH₂OH is _______than that of CH₃CH₂CH₂SH.

Question 77

If the K_a of isopropyl alcohol is 1.0 × 10^-17, the pK_a of isopropyl alcohol______.

Question 78

What is the IUPAC name of the following compound (shown as a Fischer projection)?

Question 79

Consider the following structures. Structure(s)____could be used to produce an aldehyde by reaction with PCC. Enter the number of the appropriate structure. If more than one structure is correct, enter the appropriate numbers separated by commas.

Question 80

What is the major organic product obtained from the following reaction?