Deck 13: Alcohols, phenols, and Ethers

Question 1

What is the correct classification for the alcohol shown below?

A) primary
B) secondary
C) tertiary
D) quaternary

Answer 1

secondary

Question 2

Compare glycerol with ethanol.

A) They both contain 3 carbons in the skeleton.
B) They both have the hydroxy on an interior carbon.
C) Glycerol is a long chain alcohol;ethanol is a short chain alcohol.
D) Glycerol is a triol;ethanol is not a triol.

Answer 2

Glycerol is a long chain alcohol;ethanol is a short chain alcohol.

Question 3

Which compound would be the most soluble in water?

A) CH₃-O-CH₂-CH₂-CH₃
B) CH₃-CH₂-CH₂-CH₂-CH₃
C) CH₃-CH₂-O-CH₂-CH₃
D) CH₃-CH₂-CH₂-CH₂-OH

Answer 3

CH₃-CH₂-CH₂-CH₂-OH

Question 4

Identify the correct statement with respect to the oxygen found in an alcohol as compared to the oxygen found in an ether.

A) Oxygen is identical in both these compounds;the difference between them is determined by another factor.
B) Oxygen in an alcohol is directly associated with a hydrogen;the oxygen in an ether is not chemically bound to a hydrogen.
C) Oxygen is similar in both compounds as it is always found on a terminal carbon.
D) The oxygen in an ether is found on a side chain and that of the alcohol is not.

Question 5

Which of the following compounds is correctly classified as a tertiary alcohol?

A) 3-methyl-1-butanol
B) 2-methyl-1-butanol
C) 3-methyl-2-butanol
D) 2-methyl-2-butanol

Question 6

What is the correct IUPAC name for compound shown?

A) 1,2-cyclopentadiol
B) 1,5-cyclopentanediol
C) 1,2-cyclopentanediol
D) 1,5-cyclopentadiol

Question 7

What is the correct IUPAC name for the compound shown?

A) 2-ethyl-1-pentanol
B) 1-ethylpentanol
C) 1-ethylcyclopentanol
D) 2-methylcyclopentanol

Question 8

What is the correct IUPAC name for the following compound?

A) 3-methylpentanol
B) 2-ethyl-1-butanol
C) 2-ethylbutanol
D) 1-ethyl-2-butanol

Question 9

Oxidation of CH₃CH₂CH₂CH₂OH produces CH₃CH₂CH₂CHO,which may be further oxidized to which of the following?

A)

B)

C)

D)

Question 10

Which of the following would be made from an alcohol by a dehydration reaction?

A) alkyne
B) alkene
C) alkane
D) alkyl halide

Question 11

What is the group that distinguishes alcohols from other classes of compounds?

A) carboxyl
B) carbonyl
C) hydroxy
D) amide

Question 12

The alcohol groups in the compound shown are ____.

A) are both primary
B) are both secondary
C) are both tertiary
D) one is primary and one is tertiary

Question 13

Which compound would have the highest boiling point?

A) CH₃-O-CH₂-CH₂-CH₃
B) CH₃-CH₂-CH₂-CH₂-CH₃
C) CH₃-CH₂-O-CH₂-CH₃
D) CH₃-CH₂-CH₂-CH₂-OH

Question 14

What is the organic product of the following reaction.

A)

B)

C)

D) No reaction

Question 15

Which of the following would be only very slightly soluble in water?

A) 1-propanol
B) 2-propanol
C) 1,5-pentanediol
D) 1-hexanol

Question 16

Which of the following best represents hydrogen bonding in methanol?

A)

B)

C)

D)

Question 17

What conditions must be used to carry out the following reaction?
2CH₃CH₂CH₂-OH $\rarr$ CH₃CH₂-O-CH₂CH₃ + H₂O

A) H₂SO₄,180 ^$\circ$ C
B) H₂SO₄,140 ^$\circ$ C
C) HCl
D) NaOH

Question 18

Which of the following is a secondary alcohol?

A) CH₃CH₂OH
B) (CH₃)₂CHOH
C) (CH₃)₂CHCH₂OH
D) (CH₃)₃COH

Question 19

To which class of compounds does cholesterol belong?

A) an aromatic compound
B) an ether
C) a multiple chain cyclic compound
D) an alcohol

Question 20

What is the name of the compound shown?

A) 1,3-dibromophenol
B) 3,5-dibromophenol
C) 2,4-dibromophenol
D) 1,5-dibromophenol

Question 21

Which of the following is contained in rubbing alcohol?

A) (CH₂CH(OH)CH₃)
B) (CH₂C(OH)(CH₃)₂)
C) (CH₃CH₂CH₂OH)
D) ( CH₂C(OH)(CH₃)₂)

Question 22

Select the correct IUPAC name of the following compound.

A) 3-methyl-1-methylbutane
B) 1-methoxy-3-methylpentane
C) methyl-3-methylpentyl ether
D) 1-methoxy-3-methylbutane

Question 23

Which alcohol is found in alcoholic beverages?

A) methyl alcohol
B) ethyl alcohol
C) denatured alcohol
D) wood alcohol

Question 24

An example of a heavy metal ion which reacts with R-SH is _____ .

A) Na⁺
B) Na
C) Pb²⁺
D) Mg²⁺

Question 25

How can the solubility of alcohols be estimated?

A) number of alcohol groups
B) number of secondary carbons
C) ratio of hydroxyl groups to carbons
D) number of side chains

Question 26

Ethers generally have boiling points ____ those of comparable alcohols.

A) above
B) about the same as
C) below
D) unable to predict

Question 27

Oxidation of a thiol produces a _____ .

A) salt
B) aldehyde
C) ketone
D) disulfide

Question 28

Which compound would be the least soluble in water?

A) CH₃-O-CH₂-CH₂-CH₃
B) CH₃-CH₂-CH₂-CH₂-CH₃
C) CH₃-CH₂-O-CH₂-CH₃
D) CH₃-CH₂-CH₂-CH₂-OH

Question 29

Which of the following compounds would you expect to be foul smelling?

A) CH₃CH₂CH₂OH
B) CH₃CH₂CH₂SH
C) CH₃CH₂CH₂CH₃
D) CH₃CH₂CH₂CHO

Question 30

When phenol dissolves in water,it functions as

A) a weak base.
B) a weak acid.
C) an oxidizing agent.
D) a reducing agent.

Question 31

Which of the following is produced in the reaction below?

A) CH₃CH₂SSCH₂CH₃
B) CH₃CH₂SHgSCH₂CH₃
C) CH₃CH₂HgCH₂CH₃
D) HSHgSH

Question 32

Ethers are ____ in water.

A) slightly soluble
B) very soluble
C) completely insoluble
D) unstable

Question 33

A phenol used as an antioxidant food additive in vegetable oil is _____ .

A) THC
B) BHT
C) Vitamin E
D) thymol

Question 34

The phenol in poison ivy sap that causes the skin on some people to blister is?

A) urushiol
B) safrole
C) o-phenylphenol
D) hyoxylresorcinol

Question 35

Glycerol is used as a

A) fuel additive.
B) moistening agent.
C) solvent.
D) hydraulic fluid.

Question 36

Which of the following is used in automobile antifreeze?

A) ethylene glycol
B) glycerol
C) ethyl alcohol
D) isopropyl alcohol

Question 37

The chemical reactivity of ethers is most similar to which of the following?

A) alcohols
B) alkenes
C) aromatics
D) alkanes

Question 38

The phenol used in some mouthwashes and throat lozenges is _____ .

A) cannabinol
B) cresol
C) hexachlorophene
D) hexylresorcinol

Question 39

The IUPAC name of ethyl methyl ether is _____ .

A) 1-methoxyethane
B) ethoxymethane
C) 2-methoxyethane
D) 1-etoxymethape

Question 40

Which of the following alcohols would be the most difficult to oxidize?

A) CH₃C(OH)(CH₃)₂
B) CH₃CH(OH)CH₂(CH₃)₂
C) CH₃OH
D) HOCH₂CH₂OH

Question 41

Which of the following is a tertiary alcohol?

A)

B)

C)

D)

Question 42

Which of the following compounds would be considered polyfunctional?

A) 1
B) 2
C) 3
D) All of them

Question 43

Which of the following is the most soluble in water?

A) 1-heptanol
B) heptane
C) 1-pentanol
D) pentane

Question 44

Oxidation of a secondary alcohol will produce a(n)________.

A) alkene
B) aldehyde
C) ketone
D) ether

Question 45

What is the IUPAC name for the following compound?

A) cis-4,5-dimethyl-4-heptene-2-ol
B) trans-5-ethyl-4-methyl-4-heptene-2-ol
C) 5-ethyl-4-methyl-trans-4-heptene-2-ol
D) cis-4,5-dimethyl-2,4-heptenol

Question 46

Which of the following compound classes is most likely to have an offensive odor?

A) alkenes
B) alcohols
C) ethers
D) thiols

Question 47

Predict the major product of the following reaction.

A)

B)

C)

D)

Question 48

Dehydration of an alcohol will produce a(n)______.

A) alcohol
B) ether
C) alkene
D) carbonyl

Question 49

Oxidation of a tertiary alcohol will produce a(n)____.

A) ketone
B) aldehyde
C) carboxylic acid
D) no reaction

Question 50

Thiols create the unpleasant odor associated with a skunk.Which of the general forms below represents a thiol?

A) R-S₂-R
B) R-SH₂
C) R-SH
D) R-S-R

Question 51

In the acid catalyzed dehydration of an alcohol,the acid catalyst

A) removes an hydrogen atom from -OH the to form an intermediate.
B) removes the -OH to form water.
C) protonates the intermediate to form the product.
D) protonates the -OH to form an intermediate.

Question 52

The hydration of propene would result in the formation of which of the following species?

A)

B)

C)

D)

Question 53

Which should be used to produce the following compound by oxidation?

A)

B)

C)

D) None of these

Question 54

In order to carry out the following reaction which of the following reagents would be needed?

A) (O)followed by (H)
B) (H)followed by H₂SO₄
C) H₂O/ H₂SO₄ followed by (O)
D) (O)followed by H₂SO₄

Question 55

One of the original anesthetics,diethyl ether has been replaced by more suitable substances.Of the many reasons,which of the following properties of ethers would account for it no longer being used in modern operating rooms?

A) lack of hydrogen bonding
B) high volatility
C) flammability
D) peroxide formation

Question 56

An infant with fetal alcohol syndrome could exhibit which of the following characteristics?

A) thin upper lip
B) short nasal bridge
C) mental retardation
D) all of the choices

Question 57

The product of the following reaction would be what?
2 CH₃CH₂ SH + (O) $\rarr$

A) 2 CH₃CH₂ OH
B) CH₃CH₂ S-SCH₂CH₃
C) CH₃CH₂ SCH₂CH₃
D) CH₃CH₂ SH-SHCH₂CH₃

Question 58

Complete the following reaction.

A)

B)

C)

D)

Question 59

Which of the following is produced from the following reaction?

A)

B)

C)

D)

Question 60

What is the IUPAC name for HOCH₂CHOHCH₂OH?

A) glycerol
B) triisopropyl alcohol
C) 1-hydroxy-2,3-propanediol
D) 1,2,3-propanetriol

Question 61

Functional groups are usually the center of reactivity in an organic compound.

Question 62

Phenol earned a place in history as an antiseptic,but is commonly used today as an anesthetic.

Question 63

Although diethyl ether was used as an anesthetic in the past,the use of diethyl ether in modern times is as a solvent.

Question 64

Secondary alcohols are usually oxidized to aldehydes.

Question 65

Mercaptan is another name for a thiol.

Question 66

Only alcohols contain an oxygen bearing functional group.

Question 67

Disulfides are easily oxidized to thiols.

Question 68

Thiols are more easily oxidized than alcohols.

Question 69

Testosterone,the principle male sex hormone,is shown below.It would best be classified as which of the following?

A) alcohol
B) ketone
C) alkene
D) polyfunctional

Question 70

Methyl alcohol can be dehydrated to form an alkene.

Question 71

Because phenol contains a hydroxy,it is referred to as an alcohol,but the presence of the benzene ring takes phenol out of the alcohol class.The reason is that phenol is remarkably stable and is not able to react chemically as an alcohol.

Question 72

Alcohols can form either alkenes or ethers upon dehydration.

Question 73

Tertiary alcohols are the most easily oxidized.

Question 74

The products of the complete oxidation of an alcohol are carbon dioxide and water.

Question 75

Primary alcohols can be oxidized either to aldehydes or carboxylic acids.

Question 76

Thiols are not found in nature.

Question 77

Those persons who are allergic to the sap of the poison ivy plant are responding to a phenol,urushiol.

Question 78

The solubility of long chain alcohols possessing one hydroxy is poor due to the hydrophobic nature of the alkyl portion of the molecule.

Question 79

Heavy metal ions can bind to thiol groups.

Question 80

All alcohols are produced by the processes of fermentation.