General organic and biological chemistry 5e timberlack test bank chapter 13

A isopropyl ether B diethyl ether C dimethyl ether D ethyl methyl ether E 1-propanol Answer: D Objective: 13.2 Global Outcomes: GO2 22 What is the common name of the ether that is an iso

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General, Organic & Biological Chemistry, 5e (Timberlake)

Chapter 13 Alcohols, Phenols, Thiols, and Ethers

13.1 Multiple-Choice Questions

1) Which one of the following compounds is an alcohol?

A) OH

|

CH3 - CH - CH3

CH3 - CH2 - CH

C) CH3 - CH = CH - CH2 - CH3

D) CH3 - CH2 - O - CH2 - CH3

E) CH3 - SH

Answer: A

Objective: 13.1

Global Outcomes: GO2

2) The compound CH3 - CH2 - SH is in the organic family known as

A) ethers

B) thiols

C) alcohols

D) sulfides

E) amino acids

Answer: B

Objective: 13.1

3) Alcohols contain which functional group?

A) amine

B) amide

C) hydroxyl

D) thiol

Answer: C

Objective: 13.1

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4) What is the IUPAC name for this compound?

A) 3-methyl-1-hexanol

B) 3-methyl-1-pentanol

C) 3-methyl-5-pentanol

D) 3-methyl-6-hexanol

E) 3-methylpentanol

Answer: B

Objective: 13.1

5) Which of the following is the IUPAC name for the compound below?

A) 5-methyl-4-hexanol

B) 5-methyl-4-pentanol

C) 2-methyl-3-hexanol

D) 2-methyl-3-pentanol

E) 2-methyl-3-heptanol

Answer: C

Objective: 13.1

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6) The condensed structural formula for 2,3-dichloro-4-methylcyclohexanol is A)

B)

C)

D)

E)

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7) What is the IUPAC name of this compound?

OH

|

CH3 - C - CH3

|

CH3

A) butanol

B) propanol

C) 2-propanol

D) 2-methylbutanol

E) 2-methyl-2-propanol

Answer: E

Objective: 13.1

8) Which one of the following compounds is a thiol?

A) OH

|

CH3 - CH - CH3

CH3 - CH2 - CH

C) CH3 - CH = CH - CH2 - CH3

D) CH3 - CH2 - O - CH2 - CH3

E) CH3 - SH

Answer: E

Objective: 13.1

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9) What is the name for this compound?

A) 2-bromo-5-ethylcyclohexanol

B) 2-bromo-5-ethylphenol

C) 4-bromo-1-ethyl-5-phenol

D) 6-bromo-3-ethylphenol

E) 2-bromo-5-methylphenol

Answer: B

Objective: 13.1

10) What is the name for this compound?

A) cyclopentanol

B) cyclohexanol

C) cyclobenzenol

D) phenol

E) glycerol

Answer: D

Objective: 13.1

11) A phenol has an -OH group bonded to a(n)

A) singly substituted or unsubstituted carbon

B) disubstituted carbon

C) trisubstituted carbon

D) aromatic carbon

E) tetrasubstituted carbon

Answer: D

Objective: 13.1

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12) Thiols have structures similar to alcohols except that they contain A) three alcohol groups

B) more than one carbon

C) sulfur in place of oxygen in the functional group

D) lithium in place of oxygen in the functional group

E) nitrogen in place of oxygen in the functional group

Answer: C

Objective: 13.1

13) Methanol is used in all the following except

A) making plastics

B) racing fuel

C) alcoholic beverages

D) solvents

E) paint remover

Answer: C

Objective: 13.1

14) 1,2-ethanediol (ethylene diol) has uses that include

A) antifreeze

B) solvent for paint

C) production of synthetic fibers

D) solvent for ink

E) All of the above

Answer: E

Objective: 13.1

15) What is the IUPAC name for CH3 - CH2 - CH2 - SH?

A) 1-propanethiol

B) 2-propanethiol

C) 1-butanethiol

D) 2-butanethiol

E) propyl thiol

Answer: A

Objective: 13.1

16) Thiols are strong-smelling compounds responsible for

A) fruity odors

B) sharp odors

C) flowery odors

D) skunky or bad smelling odors

E) salty odors

Answer: D

Objective: 13.1

17) What is the name of this compound?

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A) cyclopentyl propyl ether

B) cyclopentyl propyl ketone

C) 1-cyclopropyl-1-propylalcohol

D) propylcyclopentanol

E) 3-cyclopentylpropanol

Answer: A

Objective: 13.2

18) The common name for the compound CH3 - CH2 - CH2 - O - CH2 - CH3 is A) 3-pentanol

B) ethyl propyl ether

C) 3-hexanol

D) 3-ether pentane

E) ethyl propyl ketone

Answer: B

Objective: 13.2

19) The common name of CH3 - CH2 - O - CH2 - CH3 is

A) dimethyl ether

B) diethyl ether

C) 2-etherbutane

D) butyl ether

E) dibutyl ether

Answer: B

Objective: 13.2

20) Why has diethyl ether been replaced as a general anesthetic?

A) It causes unpleasant side effects in many patients

B) It is slightly polar

C) It can hydrogen bond to water

D) It is not very reactive

E) It is slightly soluble in water

Answer: A

Objective: 13.2

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21) What is the common name of the ether that is an isomer of 2-propanol? A) isopropyl ether

B) diethyl ether

C) dimethyl ether

D) ethyl methyl ether

E) 1-propanol

Answer: D

Objective: 13.2

22) What is the common name of the ether that is an isomer of 1-butanol? A) isopropyl ether

B) diethyl ether

C) dimethyl ether

D) ethyl methyl ether

E) butyl ether

Answer: B

Objective: 13.2

23) The alcohol in this list that would be most soluble in water is

A) ethanol

B) 1-butanol

C) 1-pentanol

D) 1-hexanol

E) 1-heptanol

Answer: A

Objective: 13.3

24) Which of the following compounds is a weak acid?

A) ethanol

B) ethanal

C) phenol

D) cyclohexanol

E) acetone

Answer: C

Objective: 13.3

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25) Which of the following compounds is a secondary alcohol?

A) CH3 - CH - O - CH3

|

CH3

B) CH3OH

|

CH3 - CH2 - C - CH3

|

CH3

D) CH3

|

CH3 - C - CH3

|

OH

E) CH3 - CH - OH

|

CH3

Answer: E

Objective: 13.3

26) In a tertiary alcohol, how many alkyl groups are attached to the carbon atom bonded to the -OH group?

A) none

B) one

C) two

D) three

E) four

Answer: D

Objective: 13.3

27) A primary alcohol has a hydroxyl group bonded to a(n)

D) aromatic carbon

Answer: A

Objective: 13.3

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28) A secondary alcohol has a hydroxyl group bonded to a(n)

D) aromatic carbon

Answer: B

Objective: 13.3

29) A tertiary alcohol has a hydroxyl group bonded to a(n)

D) triple-bonded carbon

E) double bonded carbon

Answer: C

Objective: 13.3

30) What kind of bonds do alcohols form between individual molecules? A) oxygen bonds

B) hydrogen bonds

C) single bonds

D) carbon bonds

E) ionic bonds

Answer: B

Objective: 13.3

31) The dehydration of an alcohol in the presence of a strong acid yields A) an alkane

B) an alkene

C) a ketone

D) an alcohol

E) an aldehyde

Answer: B

Objective: 13.4

32) The dehydration product of CH3 - CH2 - CH2 - OH in the presence of acid is A) CH2 = C = CH2

B) cyclopropane

C) cyclopropene

D) propene

E) propyne

Answer: D

Objective: 13.4

33) When 2-methyl-2-butanol undergoes dehydration in acid, one product is A) 2-methyl-2-butene

B) 2-methylbutanone

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34) In the oxidation of an alcohol to a ketone, there is

A) a loss of hydrogen

B) a loss of oxygen

C) a loss of carbon

D) a gain of hydrogen

E) a gain of oxygen

Answer: A

Objective: 13.4

35) What is the product when this compound undergoes oxidation?

CH3

|

CH3 - C - CH2 - CH2 - OH

|

CH3

A) hexanal

B) 2,2-dimethylbutanal

C) 2,2-dimethyl-4-butanone

D) 3,3-dimethyl-1-butanone

E) 3,3-dimethylbutanal

Answer: E

Objective: 13.4

36) What type of alcohol undergoes oxidation to yield a ketone? A) primary alcohol

B) both primary and secondary alcohols

C) secondary alcohol

D) all classes of alcohols

E) both secondary and tertiary alcohols

Answer: C

Objective: 13.4

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37) Tertiary alcohols cannot be oxidized because

A) there are no oxygen atoms to remove from the alcohol carbon

B) there are no hydrogen atoms attached to the alcohol carbon

C) the alcohol carbon is bonded to four groups so no oxygen can be added to it D) the alcohol carbon is bonded to four groups so no hydrogen can be added to it E) the alcohol carbon is too electronegative to have hydrogen removed from it Answer: B

Objective: 13.4

38) What type of alcohol is resistant to oxidation?

A) primary

B) secondary

C) tertiary

D) quaternary

E) none

Answer: C

Objective: 13.4

39) What is the product when the following compound is oxidized?

A) a ketone

B) an alkene

C) an aldehyde

D) an ether

E) an alkane

Answer: A

Objective: 13.4

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40) Which compound will undergo oxidation to yield the following?

A) pentanol

B) cyclopentane

C) cyclopentanol

D) methylcyclobutanol

E) cyclopentene

Answer: C

Objective: 13.4

41) In the dehydration of an alcohol to an alkene, what is produced in addition to the alkene? A) water

B) hydrogen

C) oxygen

D) carbon dioxide

E) carbon monoxide

Answer: A

Objective: 13.4

42) When a primary alcohol is completely oxidized, the product is

A) another alcohol

B) a carboxylic acid

C) an aldehyde

D) an alkane

E) a ketone

Answer: B

Objective: 13.4

43) Methanol is toxic because it is by the liver to carboxylic acids

A) reduced

B) protonated

C) oxidized

D) conjugated

E) hydrated

Answer: C

Objective: 13.4

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44) Secondary alcohols are oxidized to

A) carboxylic acids

B) ketones

C) aldehydes

D) esters

E) ethers

Answer: B

Objective: 13.4

45) Tertiary alcohols are oxidized to

A) secondary alcohols

B) ketones

C) aldehydes

D) carboxylic acids

E) None of the above

Answer: E

Objective: 13.4

46) Thiols can be gently oxidized to

A) disulfides

B) aldehydes

C) ketones

D) carboxylic acids

E) thioethers

Answer: A

Objective: 13.4

47) The dehydration product of OH in the presence of acid is

│ CH3 - CH- CH3 A) CH2 = C = CH2

B) cyclopropane

C) cyclopropene

D) propene

E) propyne

Answer: D

Objective: 13.4

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13.2 True/False Questions

1) Alcohols, ethers, and phenols contain oxygen with only single bonds

Answer: TRUE

Objective: 13.1

2) Alcohols, ethers, and thiols contain oxygen atoms

Answer: FALSE

Objective: 13.1

3) Thiols usually have sweet odors

Answer: FALSE

Objective: 13.1

4) 1,2,3-propanetriol is obtained during the manufacture of soap

Answer: TRUE

Objective: 13.1

5) Glycerin strongly attracts and holds water, a property that makes it useful as a skin softener in cosmetics

Answer: TRUE

Objective: 13.1

6) Diethyl ether has been replaced by halogenated anesthetics, which have fewer side effects

Answer: TRUE

Objective: 13.2

7) Ethers can only be straight chain compounds

Answer: FALSE

Objective: 13.2

8) The following compound is ethyl propyl ether

Answer: TRUE

Objective: 13.2

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9) Alcohols form hydrogen bonds; this accounts for their higher boiling points when compared to similar-sized alkanes

Answer: TRUE

Objective: 13.3

10) The oxygen atom in alcohols decreases water solubility of the molecule

Answer: FALSE

Objective: 13.3

11) Phenols behave as weak acids in water

Answer: TRUE

Objective: 13.3

12) Alcohols can form hydrogen bonds

Answer: TRUE

Objective: 13.3

13) Heptanol is a water soluble alcohol

Answer: FALSE

Objective: 13.3

14) A secondary alcohol can be easily oxidized to a carboxylic acid

Answer: FALSE

Objective: 13.4

15) Cycloalkanols are straight chain alcohols

Answer: FALSE

Objective: 13.4

16) Alcohols can be dehydrated to form alkenes

Answer: TRUE

Objective: 13.4

17) Primary alcohols can be oxidized to either aldehydes or ketones

Answer: FALSE

Objective: 13.4

18) Secondary alcohols can be oxidized to ketones

Answer: TRUE

Objective: 13.4

19) Tertiary alcohols are easily oxidized

Answer: FALSE

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A) O

CH3 - CH2 - C - CH3

CH3 - CH2 - CH

1) CH3 - CH2 - CH2 - OH

Objective: 13.4

2) CH3 - CH2 - CH - OH

| CH3 Objective: 13.4

Answers: 1) B 2) A

Match the structural formula with the correct functional group.

A) thiol

B) alcohol

C) ether

3) CH3 - CH2 - OH

Objective: 13.1

4) CH3 - CH2 - O - CH3

Objective: 13.1

5) CH3 - CH2 - SH

Objective: 13.1

Answers: 3) B 4) C 5) A

Select the correct name for the following.

A) propanethiol

B) 1-ethyl-3- hydroxycyclohexene

C) propane sulfide

D) 3-ethylphenol

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8)

Objective: 13.2

Answers: 6) A 7) E 8) D

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Classify the alcohols shown in column 1 as primary, secondary, or tertiary.

A) secondary

B) primary

C) tertiary

9) CH3 - CH2 - OH

Objective: 13.3

10) CH3

|

CH3 - C - CH2 - OH

|

CH3

Objective: 13.3

11) OH

|

CH3 - CH - CH3

Objective: 13.3

12)

Objective: 13.3

13) CH3

|

CH3 - C - CH2 - CH3

|

OH

Objective: 13.3

Answers: 9) B 10) B 11) A 12) A 13) C

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