Chapter 08 Merged

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The document discusses the nomenclature, structure, preparation and properties of ethers. Ethers are named based on the parent chain and location of ether linkages. Common methods of preparation include Williamson synthesis, dehydration of alcohols, and reactions of Grignard reagents. Ethers have lower boiling points than similar alkanes due to weaker intermolecular forces.

Ethers are named as alkyl substituents on oxygen atoms within a parent hydrocarbon chain. The IUPAC name indicates the location of ether linkages as prefixes. Common ethers discussed include dimethyl ether, diethyl ether, and crown ethers.

Ethers can be prepared through Williamson synthesis using alcohols and alkyl halides, dehydration of alcohols using acid catalysts, and reactions of Grignard reagents with alkyl halides or alcohols. Specific examples discussed include the preparation of t-butyl methyl ether and diphenyl ether.

Chapter 8 -- Ethers and Epoxides

MULTIPLE CHOICE

1. What is a correct name for CH3CH2OCH2CH2CH3?


A) diethyl ether
B) dipropyl ether
C) 1-propoxyethane
D) 1-ethoxypropane
E) 3-oxypentane
ANS: D TOP: Structure and Nomenclature of Ethers

2. Which of the following molecules is the correct structure for dibenzyl ether?
A)

B)

C)

D)

E)

ANS: D TOP: Structure and Nomenclature of Ethers

3. What is the IUPAC name for the following molecule?

                                          

A) 2-bromo-4-ethyl-4-methoxypentane
B) 4-bromo-2-ethyl-2-methoxypentane
C) 2-bromo-4-methoxy-4-methylhexane
D) 2-bromo-3-methoxy-3-methylhexane
E) ethyl methyl propyl ether
ANS: C TOP: Structure and Nomenclature of Ethers
4. Which of the following molecules is named oxirane?
A)

B)

C)

D)

E)

ANS: A TOP: Structure and Nomenclature of Ethers

5. What is the correct IUPAC name for the following molecule?

                                                    

A) 1,2-dimethyloxirane
B) trans-1,2-dimethyloxirane
C) 2-butene oxide
D) cis-1,2-dimethyloxirane
E) oxobutane
ANS: B TOP: Structure and Nomenclature of Ethers

6. Which of the following molecules is correctly named diphenyl ether?


A)
B)

C)

D)

E)
ANS: B TOP: Structure and Nomenclature of Ethers

7. What is a name for the following molecule?   


                                     

A) 3-ethoxy-3-methylpropane
B) ethyl isobutyl ether
C) butyl ethyl ether
D) 2-ethoxybutane
E) 3-ethoxybutane
ANS: D TOP: Structure and Nomenclature of Ethers

8. What is the correct name for the following crown ether?


                                  

A) [8]crown-4
B) [12]crown-4
C) [4]crown-4
D) [15]crown-5
E) [18]crown-6
ANS: B TOP: Structure and Nomenclature of Ethers

9. A crown ether named [18]crown-6 has a total of         carbons and                 oxygens .


A) 18, 6
B) 6, 18
C) 24, 6
D) 6, 24
E) 12, 6
ANS: E TOP: Structure and Nomenclature of Ethers

10. The formula for 1-ethoxybutane is


A)

B)

C)
D)

E)

ANS: D TOP: Structure and Nomenclature of Ethers

11. Which one of the following molecules has the highest boiling point?
A) 3-methoxy-1-propanol
B) 1,2-dimethoxyethane
C) 1,4-butanediol
D) 1,1-dimethoxyethane
E) 2-methoxy-1-propanol
ANS: C TOP: Properties of Ethers

12. Which of the following is a Grignard reagent?


A) CH3MgCl
B) CH3Li
C) (CH3)2 CuLi
D) CH3Na
E) (CH3)2 Zn
ANS: A TOP: Preparation and Reaction of Grignard Reagents

13. Which reaction will yield CH3CH2CH2D?


A) CH3CH2CH3    + D2O
B) CH3CH2CH2MgCl    + D2O
C) CH3CH2CH2OLi      +    D2O
D) CH3CH2CH2OH    +    D2O
E) more than one of these
ANS: B TOP: Preparation and Reaction of Grignard Reagents

14. Starting with p-bromoanisole (p-bromophenyl methyl ether), what sequence of reactions will
produce p-deuterioanisole?   

                                         

A) 1. D2O    2. Br2, AlBr3


B) 1. Mg, ether 2. D2O
C) 1. D2O    2. Mg, ether
D) 1. H2SO4, D    2. Mg, ether 3. D2O
E) 1. Br2, AlBr3, 2. Mg, ether, 3. D2O
ANS: B TOP: Preparation and Reaction of Grignard Reagents

15. The products of the following are:


                

A)

B)

C)

D)

E)

ANS: B TOP: Preparation and Reaction of Grignard Reagents

16. The synthesis of dipropyl ether can be accomplished using 1-propanol.    What reactants and
conditions are necessary for this to occur?
A) Na and 180°
B) PBr3 and 140°
C) H2SO4 and 140°
D) Zn and H+
E) PCC and 180°
ANS: C TOP: Preparation of Ethers

17. The best Williamson synthesis of cyclohexyl methyl ether involves the following reaction:
A)

B)
C)

D)

E)

ANS: D TOP: Preparation of Ethers

18. What alkene reacts with methanol in an acid catalyzed reaction to produce t-butyl methyl
ether?
A) ethylene
B) 2-methylpropene
C) 2-butene
D) propene
E) 1-butene
ANS: B TOP: Preparation of Ethers

19. The best route to CH3OC(CH3)3 is


A)

B)

C)

D)

E)

ANS: B TOP: Preparation of Ethers

20. When anisole (methyl phenyl ether) is treated with concentrated HBr, which of the following
products are produced?     
  
A) I
B) II
C) III
D) IV
E) I and IV
ANS: D TOP: Preparation of Ethers

21. The mechanism by which ethers are cleaved in concentrated HI is:


A) SN1
B) SN2
C) E1
D) E2
E) none of these
ANS: B TOP: Preparation of Ethers

22. Which of the following ethers will cleave the fastest with H2O and H+?
A)
B)

C)

D)

E)

ANS: D TOP: Preparation of Ethers

23. Which of following ethers will cleave by an SN1 mechanism?


A)

B)

C)

D)

E)
ANS: D TOP: Preparation of Ethers

24. The organic products of the reaction below are

                       
are:
A) ethanol and iodobenzene.
B) ethyl iodide and iodobenzene.
C) ethanol and phenol.
D) ethyl iodide and phenol.
E) ethylene oxide and phenol.
ANS: D TOP: Preparation of Ethers

25. Which of the following molecules is classified as an organic peroxy acid?


A)

B)
C)
D)

E)

ANS: E TOP: Preparation and Reactions of Epoxides

26. The first step in the mechanism of acid catalyzed ring opening of oxirane is:
A) protonation of the oxygen in the oxirane.
B) anion attack of the carbon in the oxirane.
C) cation attack of the carbon in the oxirane.
D) formation of a stable carbocation.
E) none of the above.
ANS: A TOP: Preparation and Reactions of Epoxides

27. When cyclopentene is treated with peroxyacetic acid, the product that forms is:
A) 1,2-cyclopentanediol
B) 1,2-pentanediol
C) pentanol
D) cyclopentene oxide
E) dicyclopentyl ether
ANS: D TOP: Preparation and Reactions of Epoxides
28. The correct structure for peroxyacetic acid is:
A)
B)
C)
D)
E)

ANS: C TOP: Preparation and Reactions of Epoxides

29. What is the final product of the following sequence of reactions?

                  

A) D)

B) E)

C)

ANS: C TOP: Preparation and Reactions of Epoxides

30. Which of the following statements about ethylene oxide is false?


A) Adds HBr according to Markovnikov's rule.
B) Can act as a Lewis base.
C) Reacts with Grignard reagents to give primary alcohols.
D) Can be made from ethene, oxygen, and a catalyst.
E) Can be hydrated to ethylene glycol.
ANS: A TOP: Preparation and Reactions of Epoxides

31. Which reagent will accomplish the following reaction?

        
A) NaOH
B) CH3CO3H
C) H2O, H2SO4
D) (a) BH3 (b) NaOH, H2O2
E) CH3CO2H
ANS: B TOP: Preparation and Reactions of Epoxides

32. The product of the reaction below is

            

A) CH3CH2CH2CH3.
B) CH3CH2OCH2CH2OH.
C) CH3CH2OCH2CH2OCH2CH3.
D) CH3CH2OCH2CH2CH2OH.
E) none of the above.
F) all of the above.
ANS: B TOP: Preparation and Reactions of Epoxides

33. 1-Hexanol and 1-ethoxybutane are examples of:


A) enantiomers
B) diastereomers
C) stereoisomers
D) constitutional isomers
E) none of these
ANS: D TOP: Miscellaneous

34. What is the final product in the following reaction sequence?

                 

A)

B)

C)

D)

E) none of these
ANS: C TOP: Miscellaneous
35. 1 mole of bromocyclohexane reacts with 2 moles of Li to give:
A) cyclohexene
B) cyclohexyllithium
C) cyclohexane
D) hexane
E) hexyllithium
ANS: B TOP: Miscellaneous

36. Which of the following ethers are unsymmetrical?


A) CH3OCH2CH3
B) (CH3)2CHOCH2CH(CH3)2
C) CH3OCH3
D) CH2CH3OCH2CH3
E) both A and B
ANS: E TOP: Miscellaneous

37. A reaction that would give n-butyllithium is


A) CH3CH2CH2CH3 + Li
B) CH3CH2CH2CH2Br + 2 Li
C) CH3CH2CH2CH2Br + LiBr
D) CH3CH2CH2CH2OH + Li
E) CH3CH2CH2CH3 + CH3Li
ANS: B TOP: Miscellaneous

38. Adding Br2 in H2O will distinguish which of following pairs of compounds?
A) diisopropyl ether and hexane
B) ethyl phenyl ether and allyl phenyl ether
C) 1-butanol and methyl propyl ether
D) diethyl ether and ethanol
E) toluene and anisole
ANS: B TOP: Miscellaneous
Chapter 7 -- Alcohols, Phenols & Thiols

MULTIPLE CHOICE

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

A) I
B) II
C) III
D) IV
E) V
ANS: C TOP: Nomenclature of Alcohols

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


A)

B)

C)

D)

E)

ANS: C TOP: Nomenclature of Alcohols

3. What is the IUPAC name for isobutyl alcohol?


A) 1-butanol
B) 2-butanol
C) 2-methyl-2-butanol
D) 2-methyl-1-propanol
ANS: D TOP: Nomenclature of Alcohols

4. 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
ANS: C TOP: Nomenclature of Alcohols

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


              

                   

                  

A) I
B) II
C) III
D) IV
E) V
ANS: D TOP: Nomenclature of Alcohols

6. What is the correct name for the following molecule?


                         

A) 2-pentanol
B) 3-thiopentanol
C) 2-pentanethiol
D) 4-pentanethiol
E) pentylsulfide
ANS: C TOP: Nomenclature of Alcohols

7. 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
ANS: D TOP: Nomenclature of Alcohols

8. 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
ANS: E TOP: Nomenclature of Alcohols

9. The correct name for is

A) 2-hydroxybromobenzene.
B) 2-bromobenzyl alcohol.
C) 2-bromobenzol.
D) o-bromophenol.
E) 2-bromohexanol
ANS: D TOP: Nomenclature of Alcohols

10. The formula for 2-pentanethiol is:


A)

B)

C)

D)
E)

ANS: D TOP: Nomenclature of Alcohols

11. Which of the following molecules would be the best hydrogen bond donor?
A) CH3CH2OCH3
B) CH3CN
C) CH3OH
D) CH3SH
E) CH3CH2NH2
ANS: C TOP: Properties of Alcohols

12. Which of the following molecules would have the highest boiling point?
A) CH3CH2OH
B) CH3OCH3
C) CH3CH2Cl
D) CH3CH2CH3
E) CH3CH2I
ANS: A TOP: Properties of Alcohols

13. 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
ANS: D TOP: Properties of Alcohols

14. A Lewis acid is a:


A) proton donor
B) electron pair donor
C) electron pair acceptor
D) proton acceptor
ANS: C TOP: Acid-Base Chemistry

15. The conjugate base of carbonic acid, H2CO3, is:


A) H3CO3+
B) CO2
C) HCO3–
D) CO32-
E) CO3–
ANS: C TOP: Acid-Base Chemistry

16. If the pKa of isopropyl alcohol is 17, what is the Ka of isopropyl alcohol?
A) 17  10–17
B) 10–17
C) 10–3
D) 1017
E) 103
F) 17  1017
ANS: B TOP: Acid-Base Chemistry

17. Which of the following molecules would be the strongest Brønsted-Lowry acid?
A) H2O
B) CH4
C) HF
D) HCl
E) NH3
ANS: D TOP: Acid-Base Chemistry

18. Which of the following phenols is the strongest acid?


A) D)

B) E)

C)

ANS: B TOP: Acid-Base Chemistry

19. Which of the following is the strongest base?


A)

B)

C)
D)
E)

ANS: E TOP: Acid-Base Chemistry

20. 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.
ANS: C TOP: Acid-Base Chemistry

21. 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.
ANS: A TOP: Acid-Base Chemistry

22. The pKa of an acid whose Ka = 10–11 is


A) 1011
B) 11
C) –11
D) 3
E) –3
ANS: B TOP: Acid-Base Chemistry

23. Which of the following alcohols would react most rapidly under SN1 conditions?
A) CH3OH
B) CH3CH2OH
C) (CH3)2CHCH2OH
D) (CH3)3COH
E) CH3CH2CH2OH
ANS: D TOP: Reaction Mechanisms

24. 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 SN1 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.
ANS: C TOP: Reaction Mechanisms

25. 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.
ANS: C TOP: Reaction Mechanisms

26. 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.
ANS: E TOP: Reaction Mechanisms

27. 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
ANS: D TOP: Reactions

28. When an alcohol reacts with an alkali metal like Na, the product formed is a(n):
A) alkene
B) alkoxide
C) acetylide
D) alkane
E) hydroxide
F) alkyne
ANS: B TOP: Reactions

29. 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
ANS: B TOP: Reactions

30. 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
ANS: C TOP: Reactions

31. Which of the following mixtures would NOT react?

      

  

A) I
B) II
C) III
D) IV
E) II and IV
ANS: E TOP: Reactions

32. What reagents would accomplish the following transformation?

                

A) 1. PCl3 2. H3O+
B) CrO , H in acetone
3
C) PCC, CH2Cl2
D) 1. Na 2. CH3OH
E) none of the above
ANS: C TOP: Reactions

33. Acid-catalyzed dehydration of 3-methyl-3-hexanol can give the following number of alkenes
(including stereoisomers):
A) 2
B) 3
C) 4
D) 5
E) 6
ANS: D TOP: Reactions

34. Cyclohexanol and phenol react similarly toward


A) sodium hydride.
B) FeBr3, Br2.
C) conc. H2SO4, heat.
D) PCl3.
E) SOCl2.
ANS: A TOP: Reactions

35. Oxidation of secondary alcohols with Jones' reagent (CrO3, H+, acetone) gives
A) carboxylic acids.
B) aldehydes.
C) ketones.
D) chromate esters.
E) tertiary alcohols.
ANS: C TOP: Reactions

36. Which of the following reagents will oxidize primary alcohols to carboxylic acids?
1. CrO3, H2SO4
2. PCC
3. PCl3
4. SOCl2
A) only 1
B) only 2
C) only 3
D) only 4
E) 1 and 2
ANS: A TOP: Reactions

37. Which of the following reagents will oxidize secondary alcohols to ketones?
1. CrO3, H2SO4
2. PCC
3. PCl3
4. SOCl2
A) only 1
B) only 2
C) only 3
D) only 4
E) 1 and 2
ANS: E TOP: Reactions

38. The reaction of phenol with bromine gives


A) hydroquinone.
B) 1,4-benzoquinone.
C) 2,4,6-tribromophenol.
D) 3,5-dibromophenol.
E) bromobenzene.
ANS: C TOP: Reactions

39. Which reagent or reagents can be used irreversibly to accomplish the following
transformation:
     
                              1.          NaH                             
                              2.          Na
                              3.          NaOH
A) only 1
B) only 2
C) only 3
D) 1 and 2
E) 1, 2, and 3
ANS: D TOP: Reactions

40. 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
ANS: B TOP: Reactions

41. What is the product of the following reaction sequence?

A) CH3CH2CH2CH2SCH3
B) CH3CH2CH2CH2OCH3
C) (CH3CH2CH2CH2S)2
D) CH3CH2CH2CH2OH
ANS: A TOP: Reactions

42. What is the major product of the following reaction?

A) CH3CH2CH=CH2
B) cis-CH3CH=CHCH3
C) trans-CH3CH=CHCH3
D) (CH3)2C=CH2
Chapter 12: Alcohols, Phenols, Thiols, and Ethers
1. What class of compounds is represented by the general formula RSH?
A) alcohols
B) ethers
C) thiols
D) phenols
E) disulfides
Ans: C

2. The compound tetrahydrocannabinol (THC) is partly responsible for the “high”


associated with smoking marijuana. Which of the following correctly represents the
organic families to which THC belongs?

A) alcohol, ether, alkene


B) phenol, alkene, ether
C) thiol, phenol, alkene
D) alcohol, thiol, alkene
E) ester, phenol, alcohol
Ans: B

3. What is another acceptable name for the compound 4-chlorophenol?


A) meta-4-chlorophenol
B) para-chlorophenol
C) meta-chlorophenol
D) ortho-chlorophenol
E) trans-4-chlorophenol
Ans: B

4. What is the IUPAC name of the compound CH3CH2CH2OH?


A) propanol
B) ethanol
C) 3-phenol
D) 1-propanol
E) 3-pentanol
Ans: D

Page 120
Chapter 12 Alcohols, Phenols, Thiols, and Ethers

5. The IUPAC name for the compound shown below is 1,2,3-propanetriol. What is the
common name of this compound?

A) glycerol
B) ethylene glycol
C) phenol
D) isopropyl alcohol
E) menthol
Ans: A

6. What is the IUPAC name of the compound shown below?

A) 1-propanol
B) 1-cyclopentanol
C) cyclopropanol
D) phenol
E) glycerol
Ans: C

7. Which of the following statements about the compound shown below is FALSE?

A) It is a tertiary alcohol.
B) Its name is 2-methyl-3-pentanol.
C) It can participate in hydrogen bonding.
D) It can be oxidized to a ketone.
E) It contains both a nonpolar and a polar region.
Ans: A

Page 121
Chapter 12 Alcohols, Phenols, Thiols, and Ethers

8. Hexylresorcinol is listed as an active ingredient in some mouthwashes and throat


lozenges. The IUPAC name for hexylresorcinol is 4-hexyl-3-hydroxyphenol. Which of
the following is its structure?

A)

B)

C)

D)

E)
Ans: B

9. Cortisol is an anti-inflammatory agent that also regulates carbohydrate metabolism.


Which of the following best describes the types of alcohols present in cortisol?

A) primary, secondary, and tertiary


B) secondary and tertiary
C) primary, tertiary, and a phenol
D) primary, secondary, and quaternary
E) primary and tertiary
Ans: A

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

10. When methanal, the simplest aldehyde, undergoes reduction by the addition of
hydrogen, what product results?
A) methanol
B) methane
C) methanone
D) formaldehyde
E) carbon dioxide
Ans: A

11. Which of the following is NOT a possible alkene product from the dehydration reaction
of 2-butanol?
A)
B)

C)

D)
E) All of the above alkenes are possible products.
Ans: C

12. What is the general classification of the reaction depicted below?

A) substitution
B) oxidation
C) addition
D) reduction
E) condensation
Ans: B

13. Which product of the oxidation of ethanol causes many of the symptoms of the
“morning-after hangover”?
A) phenol
B) resveratrol
C) ethanal
D) formaldehyde
E) ethylene glycol
Ans: C

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

14. What is the most common use of phenol derivatives in health care?
A) antiseptics/disinfectants
B) antibiotics
C) anesthetics
D) radiation therapy
E) suture material
Ans: A

15. Which statement concerning the physical properties of alcohols is FALSE?


A) Alcohols are polar and can form intermolecular hydrogen bonds.
B) 1-Pentanol is more water-soluble than pentane because 1-pentanol can hydrogen
bond with water.
C) The water solubility of an alcohol decreases with an increase in the hydrocarbon
chain.
D) Alcohols have higher boiling point temperatures than hydrocarbons and ethers of
similar molar mass.
E) The water solubility of an alcohol decreases with an increase in the number of polar
hydroxyl groups.
Ans: E

16. What is the typical medical use for the compounds shown below?

A) antiseptics/disinfectants
B) antibiotics
C) anesthetics
D) radiation therapy
E) suture material
Ans: C

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

17. Which of the following is the structure of ethyl propyl ether?


A)

B)

C)

D)

E)
Ans: A

18. Which of the following is the structure for methyl tertiary butyl ether?

A)

B)

C)

D)

E)
Ans: A

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

19. Which class of compounds is primarily responsible for the foul smell of skunk spray?
A) phenols
B) thiols
C) diols
D) acetals
E) ketones
Ans: B

20. What important type of bond, formed between two sulfhydryl (-SH) groups, plays a key
role in the shapes of many proteins?
A) cysteine bond
B) hydrogen bond
C) disulfide bond
D) thioester bond
E) double bond
Ans: C

21. What role does the thiol coenzyme A perform in biochemical reactions?
A) It serves as the energy source for energy-requiring reactions.
B) It serves as a carrier of two-carbon acetyl groups.
C) It serves as an identification marker on the surface of cells.
D) It functions as a catalyst for reduction reactions.
E) It is a structural component of muscle and bone.
Ans: B

22. What class of compounds is represented by the general formula ROR?


A) alcohols B) esters C) ethers D) aldehydes E) carboxylic acids
Ans:  C

23. What is the common name of the simplest ether?


A) dimethyl ether D) ethyl ether
B) methyl ether E) methyl ethyl ether
C) 1,2-dimethylether
Ans:  A

24. What is the name of the alcohol produced by the fermentation of sugars and starches,
and contained in alcoholic beverages?
A) methyl alcohol D) propanol
B) isopropyl alcohol E) ethanol
C) methanol
Ans:  E

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

25. Classify the alcohol shown below.

A) primary D) quaternary
B) secondary E) phenol
C) tertiary
Ans:  C

26. What is the name of the product formed in the following reaction, the catalyzed
hydrogenation of 2-butanone?

A) butane D) butanol
B) isobutyl alcohol E) butanal
C) 2-butanol
Ans:  C

27. The dehydration of an alcohol produces what type of organic compound?


A) alkane B) alkene C) alkyne D) aldehyde E) ketone
Ans:  B

28. Which type of alcohol does NOT undergo oxidation under normal conditions?
A) primary D) Both B and C are correct.
B) secondary E) All alcohols undergo oxidation.
C) tertiary
Ans:  C

29. Which statement best describes the solubility of the alcohol whose structure is shown
below?

A) It would be readily soluble in water because it contains a polar hydroxyl group.


B) It would be very soluble in water because it can hydrogen bond with water.
C) It would have limited solubility in water because the molecule is largely
hydrophobic.
D) It would be soluble in NaCl(aq) because it can dissociate into ions.
E) It is impossible to predict solubility from the structure alone.
Ans:  C

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

30. Oxidation of a secondary alcohol results in what type of compound?


A) alkene D) ketone
B) aldehyde E) ether
C) carboxylic acid
Ans:  D

31. What is the structure of the ether, 3-ethoxyhexane?


A)

B)

C)

D)

E) None of the choices are correct.


Ans:  A

32. Which of the following structures represents the compound 1,3-propanedithiol?


A) D)

B) E) None of the choices are correct.

C)

Ans:  C

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

33. Dehydration of the alcohol shown below produces styrene, an important starting
material in the polymer and plastics industry. What is the structure of styrene?

A)

B)

C)

D)

E)
Ans:  B

34. What is the name of the simplest alcohol?


A) primol B) methanal C) methanol D) ethanol E) formal
Ans:  C

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

35. Although ethanol is fit for human consumption, methanol is quite toxic if ingested. The
toxicity is due to the aldehyde produced when methanol is oxidized in the liver. Which
of the following is the aldehyde formed by the oxidation of methanol?

A)

B)

C)

D)

E)
Ans:  E

36. What is the IUPAC name of the following compound?

A) 2-methyl-3-hexanol D) 2-methyl-3-pentanol
B) 5-methyl-4-hexanol E) 2,2-dimethyl-3-pentanol
C) 3-methyl-2-hexanol
Ans:  C

37. The reduction of acetaldehyde (shown below) is an important biochemical reaction.


Which of the following is the product of its reduction?

A)

B)

C)

D)

E)
Ans:  A

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

38. Ethylene glycol is the common name for the compound with the structure:
HOCH2CH2OH. What is the IUPAC name for this compound?
A) 1,2-diethanol
B) 1,2-phenol
C) propanol
D) dihydroxyethane
E) 1,2-ethanediol
Ans:  E

39. What alcohol can cause blindness and possibly death when it is consumed?
A) ethanal B) ethanol C) methanal D) methanol E) 1,2,3-propanetriol
Ans:  D

40. Zaitsev’s rule can be used to predict the major alkene product in a dehydration reaction.
Which of the following alkenes would be the major product of the dehydration reaction
shown below?

A)

B)

C)

D)
E) All are equally likely.
Ans: B

41. Which of the following alcohols is a tertiary alcohol?


A) 1-butanol D) 2-methyl-2-butanol
B) 2-butanol E) 3,3-dimethyl-2-butanol
C) 2-methyl-1-butanol
Ans:  D

42. What is the name of the product of the reaction below, which requires acid as a catalyst?
CH2=CH2 + H2O → ?
A) ethanol B) ethanal C) methanal D) methanol E) 1,2,3-propanetriol
Ans:  A

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

43. What type of compound is produced by the hydration of an alkene?


A) aldehyde B) phenol C) alcohol D) diol E) acid
Ans:  C

44. What type of compound is produced by the reduction of aldehydes and ketones?
A) alkene B) phenol C) alkane D) carboxylic acid E) alcohol
Ans:  E

45. When an alcohol is heated with concentrated sulfuric acid (H2SO4), which of the
following reaction types is likely to occur?
A) hydration D) oxidation
B) dehydration E) substitution
C) dehydrogenation
Ans:  B

46. The hydration reaction below follows Markovnikov’s rule. Which of the following is
the expected major product of this reaction?

A)

B)

C)

D)

E)
Ans: C

47. What is the initial oxidation product of a primary alcohol?


A) alkane B) alkene C) ketone D) aldehyde E) carboxylic acid
Ans:  D

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

48. The condensation reaction between the two alcohols below produces what type of
compound?

A) alkene B) alkane C) carboxylic acid D) ester E) ether


Ans:  E

49. Which one of the following biochemical species contains a thioester bond which plays a
key role in its function?
A) NAD+ B) NADH C) DNA D) acetyl CoA E) ADP
Ans:  D

50. Which compound has been improperly named?

A)

B)

C)

D)

E) All are properly named.


Ans:  C

51. Which of the following compounds has the highest boiling point?
A) CH2(OH)CH(OH)CH2OH (molar mass = 92 g/mol)
B) CH2(OH)CH2CH2CH2OH (molar mass = 90 g/mol)
C) CH3CH2CH2CH2CH2OH (molar mass = 88 g/mol)
D) CH3CH(OH)CH2CH2OH (molar mass = 90 g/mol)
E) CH3CH2CH2CH2CH2CH3 (molar mass = 86 g/mol)
Ans:  A

52. Which statement best explains why alcohols have a higher boiling point than alkanes
with a similar molar mass?
A) Alcohols have weaker intermolecular forces than alkanes.

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

B) Alcohols have London forces only and alkanes have dipole-dipole attractions.
C) Alcohols have strong hydrogen bonding forces between molecules and alkanes
have weaker London forces.
D) Alcohols have stronger London forces than alkanes.
E) None of the choices are correct.
Ans:  C

53. What is the IUPAC name for the following alcohol?

A) 5-chloro-4-hexanol D) 3-chloro-4-butanol
B) 2-chloro-3-hexanol E) 1-chloro-1-methyl-2-pentanol
C) 1-ethylchloro-butanol
Ans:  B

54. Which of the following is expected to have the greatest solubility in water?
A) CH3OH D) CH3CH3
B) CH3CH2CH2CH2OH E) Both A and D are equally soluble.
C) CH3CH2CH2CH2CH3
Ans:  A

55. What is the common name of 2-propanol?


A) wood alcohol D) propyl alcohol
B) grain alcohol E) isopropyl alcohol
C) ethyl alcohol
Ans:  E

56. Which of the following statements concerning glycerol is FALSE?


A) Glycerol contains three hydroxyl groups.
B) Glycerol is a viscous liquid.
C) Glycerol is sweet.
D) Glycerol is a diol.
E) Glycerol is obtained as a byproduct of the hydrolysis of fats
Ans:  D

57. Which of the following is a tertiary (3o) alcohol?


A) propanol D) 1,2-ethanediol
B) 2-methyl-2-butanol E) cyclopropanol
C) 3-hexanol
Ans:  B

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

58. Which of the following will result in the formation of an alkene?


A) oxidation of an aldehyde
B) hydration of an alcohol with nickel or platinum as a catalyst
C) dehydration of an alcohol by heating with concentrated sulfuric acid
D) reduction of an alcohol by the addition of FeCl3
E) Both A and B are correct.
Ans:  C

59. Lactic acid gives sour milk its distinctive taste. What product is formed when lactic
acid is oxidized?

A)

B)

C)

D)

E)
Ans:  D

60. Glycerol (1,2,3-propanetriol) is a by-product of the hydrolysis of fats.


Ans:  True

61. A primary alcohol has two alkyl groups attached to the carbinol carbon.
Ans:  False

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Chapter 12 Alcohols, Phenols, Thiols, and Ethers

62. Dehydration of a primary alcohol produces a mixture of alkenes.


Ans:  False

63. The oxidation of a tertiary alcohol produces a ketone.


Ans:  False

64. Oxidation may be classified as the gain of bonds to oxygen, or the loss of bonds to
hydrogen.
Ans:  True

65. Stepwise oxidation of a primary alcohol produces first an ether and then a carboxylic
acid.
Ans:  False

66. The gain of an electron by an atom is called reduction.


Ans:  True

67. A phenol is a compound that contains a hydroxyl group attached to a benzene ring.
Ans:  True

68. Liquid diethyl ether contains an extensive network of hydrogen bonds.


Ans:  False

69. The formation of a disulfide bond (-S-S-) between two sulfhydryl groups (-SH) is an
oxidation process.
Ans:  True

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