Deck 7: Alcohols, Phenols Thiols

Question 1

The formula for 2-pentanethiol is:

A)
B)
C)
D)
E)

Answer 1

Question 2

Which of the following molecules would have the highest boiling point?

A) CH₃CH₂OH
B) CH₃OCH₃
C) CH₃CH₂Cl
D) CH₃CH₂CH₃
E) CH₃CH₂I

Answer 2

CH₃CH₂OH

Question 3

Which of the following molecules is classified as a tertiary (3°) alcohol?

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

Answer 3

IV

Question 4

What is the IUPAC name for isobutyl alcohol?

A) 1-butanol
B) 2-butanol
C) 2-methyl-2-butanol
D) 2-methyl-1-propanol

Question 5

Which of the following phenols is the strongest acid?

A)
B)
C)
D)
E)

Question 6

Phenols are stronger acids than alcohols because of the

A) resonance stabilization of phenoxide ions.
B) resonance stabilization of phenols.
C) resonance stabilization of alkoxide ions.
D) resonance stabilization of alcohols.
E) hydrogen bonding in phenols.

Question 7

Electron-withdrawing substituents

A) increase acidity by increasing the stability of acids.
B) decrease acidity by increasing the stability of a conjugate base.
C) increase acidity by increasing the stability of a conjugate base.
D) decrease acidity by increasing the stability of acids.
E) can only have a slight effect on acidity.

Question 8

What is the correct name for the following molecule?

A) 2-pentanol
B) 3-thiopentanol
C) 2-pentanethiol
D) 4-pentanethiol
E) pentylsulfide

Question 9

Which of the following is 3-pentyn-1-ol?

A)
B)
C)
D)
E)

Question 10

Which of the following molecules would be the strongest Brønsted-Lowry acid?

A) H₂O
B) CH₄
C) HF
D) HCl
E) NH₃

Question 11

What would be the IUPAC name for the following alcohol?

A) 2-methyl-4-pentanol
B) 2-methyl-4-hydroxypentane
C) 4-methyl-2-pentanol
D) 4-hydroxy-2-methylpentane
E) 2-hydroxy-4-methylpentane

Question 12

Which of the following molecules would be the best hydrogen bond donor?

A) CH₃CH₂OCH₃
B) CH₃CN
C) CH₃OH
D) CH₃SH
E) CH₃CH₂NH₂

Question 13

The conjugate base of carbonic acid, H₂CO₃, is:

A) H₃CO₃⁺
B) CO₂
C) HCO₃^-
D) CO₃^2-
E) CO₃^-

Question 14

The expected order of boiling points of the following is:

A) 3 > 2 > 1
B) 1 > 2 > 3
C) 1 > 3 > 2
D) 2 > 3 > 1
E) 2 > 1 > 3

Question 15

What is a correct name for (CH₃)₃CO^- Na⁺??

A) sodium alkoxide
B) sodium trimethyloxide
C) sodium butoxide
D) sodium trimethylethoxide
E) sodium tert-butoxide

Question 16

A Lewis acid is a:

A) proton donor
B) electron pair donor
C) electron pair acceptor
D) proton acceptor

Question 17

What is the name of the following alcohol?

A) 1-ethyl-2-methylbenzyl alcohol
B) methylphenylpropanol
C) 2-methyl-2-phenyl-1-propanol
D) 2-phenyl-2-butanol

Question 18

Which of the following is the strongest base?

A)
B)
C)
D)
E)

Question 19

The correct name for is

A) 2-hydroxybromobenzene.
B) 2-bromobenzyl alcohol.
C) 2-bromobenzol.
D) o-bromophenol.
E) 2-bromohexanol

Question 20

Which of the following is a secondary (2°) alcohol?

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

Question 21

Which of the following alcohols would react most rapidly under S_N1 conditions?

A) CH₃OH
B) CH₃CH₂OH
C) (CH₃)₂CHCH₂OH
D) (CH₃)₃COH
E) CH₃CH₂CH₂OH

Question 22

Which of the following mixtures would NOT react?

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

Question 23

The pK_a of an acid whose K_a = 10^-11 is

A) 10¹¹
B) 11
C) -11
D) 3
E) -3

Question 24

Which reagent will accomplish the following transformation?

A) pyridinium chlorochromate
B) K₂Cr₂O₇, H₂SO₄, H₂O
C) H₂O₂, NaOH, H₂O
D) Ag(NH₃)₂⁺, NaOH (Tollen's reagent)
E) all of the above

Question 25

What is the major product of the following reaction?

A) CH₃CH₂CH=CH₂
B) cis-CH₃CH=CHCH₃
C) trans-CH₃CH=CHCH₃
D) (CH₃)₂C=CH₂

Question 26

What type of compound is formed when a secondary (2°) alcohol is treated with Jones' reagent?

A) an alkene
B) an alkyne
C) an aldehyde
D) a ketone
E) a carboxylic acid

Question 27

Which reagents would you use to accomplish the following transformation?

A) H₂SO₄, H₂O, acetone
B) CrO₃, H₂SO₄, acetone
C) PCC/CH₂Cl₂
D) Zn, HCl, acetone
E) H₂, Pd, acetone

Question 28

What is the product of the following reaction sequence?

A) CH₃CH₂CH₂CH₂SCH₃
B) CH₃CH₂CH₂CH₂OCH₃
C) (CH₃CH₂CH₂CH₂S)₂
D) CH₃CH₂CH₂CH₂OH

Question 29

is the major product from the E1 dehydration of 2-methyl-2-hexanol?

A) 4-methyl-1-hexene
B) 4-methyl-3-hexene
C) 2-methyl-2-hexene
D) 2-methyl-1-hexene
E) 2-methylhexane

Question 30

Which statement is false? Tert-Butyl alcohol reacts

A) with HCl to give 2-methylpropene by an E1 mechanism.
B) with HCl to give 2-chloro-2-methylpropane by an S_N1 mechanism.
C) with HCl and HBr at very different rates.
D) with HCl or HBr to give a carbocation intermediate.
E) with HCl to give both 2-methylpropene and 2-chloro-2-methylpropane.

Question 31

The rate-determining step in the following reaction is:

A) protonation of the alcohol
B) ionization of the alcohol to give a carbocation.
C) loss of water from the protonated alcohol to give a carbocation
D) capture of a carbocation by bromide ion.
E) displacement of water from the protonated alcohol by bromide ion.

Question 32

The rate-determining step in the following reaction is:

A) protonation of the alcohol.
B) ionization of the alcohol to give a carbocation.
C) loss of water from the protonated alcohol to give a carbocation.
D) capture of a carbocation by bromide ion.
E) displacement of water from the protonated alcohol by bromide ion.