University of New England CHEM 1020 Chapter 7 -- Alcohols, Phenols Thiols MULTIPLE CHOICE 1)Which of the following is a secondary (2°) alcohol?             I II III IV V                                    Which of the following is 3-pentyn-1-ol?   A)       B)         C)       D)         E)                                        What is the IUPAC name for isobutyl alcohol? 1-butanol 2-butanol 2-methyl-2-butanol 2-methyl-1-propanol                                          What would be the IUPAC name for the following alcohol? 2-methyl-4-pentanol 2-methyl-4-hydroxypentane 4-methyl-2-pentanol 4-hydroxy-2-methylpentane 2-hydroxy-4-methylpentane                                    Which of the following molecules is classified as a tertiary (3°) alcohol?                         I II III IV V                                    What is the correct name for the following molecule?             2-pentanol 3-thiopentanol 2-pentanethiol 4-pentanethiol pentylsulfide                                      What is the name of the following alcohol?               1-ethyl-2-methylbenzyl alcohol methylphenylpropanol 2-methyl-2-phenyl-1-propanol 2-phenyl-2-butanol                                    What is a correct name for (CH3)3CO– Na+?? sodium alkoxide sodium trimethyloxide sodium butoxide sodium trimethylethoxide sodium tert-butoxide                                              The correct name for                           is   2-hydroxybromobenzene

University of New England

CHEM 1020

Chapter 7 -- Alcohols, Phenols Thiols

MULTIPLE CHOICE

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

1. 1. I
   2. II
   3. III
   4. IV
   5. V

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

3. What is the IUPAC name for isobutyl alcohol?
   1. 1-butanol
   2. 2-butanol
   3. 2-methyl-2-butanol
   4. 2-methyl-1-propanol

4. 
   What would be the IUPAC name for the following alcohol?
   1. 2-methyl-4-pentanol
   2. 2-methyl-4-hydroxypentane
   3. 4-methyl-2-pentanol
   4. 4-hydroxy-2-methylpentane
   5. 2-hydroxy-4-methylpentane

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

1. 1. I
   2. II
   3. III
   4. IV
   5. V

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

1. 1. 2-pentanol
   2. 3-thiopentanol
   3. 2-pentanethiol
   4. 4-pentanethiol
   5. pentylsulfide

7. What is the name of the following alcohol?

1. 1. 1-ethyl-2-methylbenzyl alcohol
   2. methylphenylpropanol
   3. 2-methyl-2-phenyl-1-propanol
   4. 2-phenyl-2-butanol

8. What is a correct name for (CH₃)₃CO^– Na⁺??
   1. sodium alkoxide
   2. sodium trimethyloxide
   3. sodium butoxide
   4. sodium trimethylethoxide
   5. sodium tert-butoxide

9. The correct name for                           is

1. 1. 2-hydroxybromobenzene.
   2. 2-bromobenzyl alcohol.
   3. 2-bromobenzol.
   4. o-bromophenol.
   5. 2-bromohexanol

10. The formula for 2-pentanethiol is:

11. Which of the following molecules would be the best hydrogen bond donor?
    1. CH₃CH₂OCH₃
    2. CH₃CN
    3. CH₃OH
    4. CH₃SH
    5. CH₃CH₂NH₂

12. Which of the following molecules would have the highest boiling point?
    1. CH₃CH₂OH
    2. CH₃OCH₃
    3. CH₃CH₂Cl
    4. CH₃CH₂CH₃
    5. CH₃CH₂I

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

14. A Lewis acid is a:
    1. proton donor
    2. electron pair donor
    3. electron pair acceptor
    4. proton acceptor

15. The conjugate base of carbonic acid, H₂CO₃, is:
    1. H₃CO₃⁺
    2. CO₂
    3. HCO₃^–
    4. CO₃^2-
    5. CO₃^–

16. If the pK_a of isopropyl alcohol is 17, what is the K_a of isopropyl alcohol?

A) 17 ? 10^–17

B) 10–17

C) 10–3

D) 1017

E) 103

F) 17 ? 10¹⁷

17. Which of the following molecules would be the strongest Brønsted-Lowry acid?
    1. H₂O
    2. CH₄
    3. HF
    4. HCl
    5. NH₃

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

    1. 

       

       D)

1. 2. 

      

      E)

C)

19. Which of the following is the strongest base?

D)   

E)   

20. Electron-withdrawing substituents
    1. increase acidity by increasing the stability of acids.

1. 2. decrease acidity by increasing the stability of a conjugate base.
   3. increase acidity by increasing the stability of a conjugate base.
   4. decrease acidity by increasing the stability of acids.
   5. can only have a slight effect on acidity.

21. Phenols are stronger acids than alcohols because of the
    1. resonance stabilization of phenoxide ions.
    2. resonance stabilization of phenols.
    3. resonance stabilization of alkoxide ions.
    4. resonance stabilization of alcohols.
    5. hydrogen bonding in phenols.

22. The pK_a of an acid whose K_a = 10^–11 is

A) 10¹¹

B) 11

C) –11

4. 3
5. –3

23. Which of the following alcohols would react most rapidly under S_N1 conditions?
    1. CH₃OH
    2. CH₃CH₂OH
    3. (CH₃)₂CHCH₂OH
    4. (CH₃)₃COH
    5. CH₃CH₂CH₂OH

24. Which statement is false? Tert-Butyl alcohol reacts
    1. with HCl to give 2-methylpropene by an E1 mechanism.
    2. with HCl to give 2-chloro-2-methylpropane by an S_N1 mechanism.
    3. with HCl and HBr at very different rates.
    4. with HCl or HBr to give a carbocation intermediate.
    5. with HCl to give both 2-methylpropene and 2-chloro-2-methylpropane.

25. The rate-determining step in the following reaction is:

1. 1. protonation of the alcohol.
   2. ionization of the alcohol to give a carbocation.
   3. loss of water from the protonated alcohol to give a carbocation.
   4. capture of a carbocation by bromide ion.
   5. displacement of water from the protonated alcohol by bromide ion.

26. The rate-determining step in the following reaction is:

1. 1. protonation of the alcohol
   2. ionization of the alcohol to give a carbocation.
   3. loss of water from the protonated alcohol to give a carbocation
   4. capture of a carbocation by bromide ion.
   5. displacement of water from the protonated alcohol by bromide ion.

27. What type of compound is formed when a secondary (2°) alcohol is treated with Jones' reagent?
    1. an alkene
    2. an alkyne
    3. an aldehyde
    4. a ketone
    5. a carboxylic acid

28. When an alcohol reacts with an alkali metal like Na, the product formed is a(n):
    1. alkene
    2. alkoxide
    3. acetylide
    4. alkane
    5. hydroxide
    6. alkyne

29. 
    Which reagents would you use to accomplish the following transformation?

1. 1. H₂SO₄, H₂O, acetone
   2. CrO₃, H₂SO₄, acetone
   3. PCC/CH₂Cl₂
   4. Zn, HCl, acetone
   5. H₂, Pd, acetone

30. is the major product from the E1 dehydration of 2-methyl-2-hexanol?
    1. 4-methyl-1-hexene
    2. 4-methyl-3-hexene
    3. 2-methyl-2-hexene

1. 4. 2-methyl-1-hexene
   5. 2-methylhexane

31. Which of the following mixtures would NOT react?

1. 1. I
   2. II
   3. III
   4. IV
   5. II and IV

32. 
    What reagents would accomplish the following transformation?

1. 1. 1. PCl₃ 2. H₃O⁺

   2. 

      CrO₃, H   in acetone
   3. PCC, CH₂Cl₂
   4. 1. Na 2. CH₃OH
   5. none of the above

33. Acid-catalyzed dehydration of 3-methyl-3-hexanol can give the following number of alkenes (including stereoisomers):
    1. 2
    2. 3
    3. 4
    4. 5
    5. 6

34. Cyclohexanol and phenol react similarly toward
    1. sodium hydride.
    2. FeBr₃, Br₂.

1. 3. conc. H₂SO₄, heat.
   4. PCl₃.
   5. SOCl₂.

35. Oxidation of secondary alcohols with Jones' reagent (CrO₃, H⁺, acetone) gives
    1. carboxylic acids.
    2. aldehydes.
    3. ketones.
    4. chromate esters.
    5. tertiary alcohols.

36. Which of the following reagents will oxidize primary alcohols to carboxylic acids?

1. CrO₃, H₂SO₄
2. PCC
3. PCl₃
4. SOCl₂

1. only 1
2. only 2
3. only 3
4. only 4
5. 1 and 2

37. Which of the following reagents will oxidize secondary alcohols to ketones?

1. CrO₃, H₂SO₄
2. PCC
3. PCl₃
4. SOCl₂

1. only 1
2. only 2
3. only 3
4. only 4
5. 1 and 2

38. The reaction of phenol with bromine gives
    1. hydroquinone.
    2. 1,4-benzoquinone.
    3. 2,4,6-tribromophenol.
    4. 3,5-dibromophenol.
    5. bromobenzene.

39. Which reagent or reagents can be used irreversibly to accomplish the following transformation:

1. NaH
2. Na
3. NaOH
   1. only 1
   2. only 2
   3. only 3
   4. 1 and 2
   5. 1, 2, and 3

40. Which reagent will accomplish the following transformation?

1. 1. pyridinium chlorochromate
   2. K₂Cr₂O₇, H₂SO₄, H₂O
   3. H₂O₂, NaOH, H₂O
   4.  

1. 5. all of the above

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

1. 1. CH₃CH₂CH₂CH₂SCH₃
   2. CH₃CH₂CH₂CH₂OCH₃
   3. (CH₃CH₂CH₂CH₂S)₂
   4. CH₃CH₂CH₂CH₂OH

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

1. 1. CH₃CH₂CH=CH₂
   2. cis-CH₃CH=CHCH₃
   3. trans-CH₃CH=CHCH₃
   4. (CH₃)₂C=CH₂