Exam I - Practice II

QOI 0809 OH #1
Name___________________________________
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
1) __________, also known as wood alcohol, is used as a fuel and as a solvent. Ingestion of
this alcohol can lead to blindness and death.
1)
2) __________ is dissolved in water to make the solution sold commercially as rubbing

alcohol.
2)
3) __________, commonly used in automobile antifreezes, is a diol which is highly toxic if

ingested.
3)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
4) What type of orbital do the lone pair electrons on oxygen occupy in ethanol?
A) sp3
B)
C) sp
D) p
4)
E)
5) What two atomic orbitals or hybrid atomic orbitals overlap to form the CO bond in ethanol?
A) C sp3 + O sp3
B) C sp2 + O sp2
C) C sp3 + O sp2
D) C sp2 + O sp3
E) none of the above
5)
6) Provide the structure of the major organic product in the reaction below.
6)
7)
8)
(CH3 )2CHCH2 CH2 CHO
9)
1. LiAlH4
2. H3 O+
10)
11) Provide the reagents necessary to carry out the transformation shown below.
11)
12) Provide the reagents necessary to carry out the transformation shown below.
12)
13) 2-Methylbutan-1-ol is classified as __________.
A) an enol
B) a primary alcohol
C) a secondary alcohol
D) a phenol
E) a tertiary alcohol
13)
14) 1-Methylcyclopentan-1-ol is classified as __________.

A) a primary alcohol
B) a tertiary alcohol
D) a phenol
E) an enol
14)
15) 2-Methylpentan-3-ol is classified as __________.

A) a tertiary alcohol
B) a primary alcohol
D) a phenol
E) an enol
15)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
16) Provide an acceptable name for the compound below.

HOCH2 CH2 OH
(CH3 )2CHCH2 OH
26) Which is more soluble in water, butan-1-ol or decan-1-ol? Explain briefly.

27) __________ is the major intermolecular attraction responsible for the relatively high boiling
points of alcohols.
27)
28) Distillation of mixtures of ethanol and water cannot increase the ethanol content of the
mixture above 95% because this solution boils at a lower temperature than either pure
ethanol or pure water. The term which describes this lower boiling mixture is __________.
28)
29) Ethanol that contains added impurities that make it unfit for drinking is described as
__________.
29)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
30) How would one used a Grignard-based synthesis to accomplish the following transformation?
pentanal (CH3 CH2 CH2 CH2CHO) to heptan-3-ol
methyl isobutyrate [(CH3 )2CHCO2 CH3 ] to 3-ethyl-2-methylpentan-3-ol
benzyl bromide (PhCH2 Br) to 3-phenylpropan-1-ol
33) Provide the reagents necessary to accomplish the following transformation.

2-methyl-2-octene to 2-methyloctan-3-ol
methyl benzoate (PhCO2 CH3 ) to benzyl alcohol (PhCH2 OH)
37) Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors
reactants or products.
CH3 CH2O- + NH3
38) Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors
reactants or products.
CH3 O- + HCl
39) Explain why phenol is about 106 times more acidic than methanol. Use appropriate resonance structures as part
of your explanation.
40) Which is the stronger acid, phenol or 4-nitrophenol?
41) Which is the stronger acid, cyclohexanol or 2-fluorocyclohexan-1-ol?
42) Explain how a mixture of phenol and cyclopentanol might be separated using differences in their solubility
properties.
43) Provide the reagents necessary to convert (R)-3-methylpent-1-ene to (R)-3-methylpentan-1-ol.
44) Provide the reagents necessary to convert (E)-but-2-ene to meso-butane-2,3-diol.
45) Provide the reagents necessary to carry out the conversion shown below.
46) Provide the structure of the major organic product in the reaction shown below.
CH3 CH2CH2 CHO
1. (CH3 )2 CHMgBr
2. H3 O+
52) A novice chemist wished to prepare 1-methylcyclohexane-1,4-diol from the keto alcohol shown below by
treating it with the appropriate Grignard reagent. Was the chemist successful? Explain.
53) Point out the flaw in the synthetic scheme shown below.
54) Provide a detailed, stepwise mechanism for the reaction of acetyl chloride (CH3 COCl) and 2 equivalents of
PhMgCl.
55) Why are ether solvents used in the preparation of Grignard and organolithium reagents?
(CH3 )2CHC1
1. Li
2. 0.5 CuI
3. CH3 CH2CH2 I
57) Show how one might prepare 3-methylpentane by beginning with 2-iodobutane and employing the
Corey-House reaction.
60) Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?
A) CH3 COCH2 CH2 Br
B) H2NCH2 CH2 Br
C) BrCH2 CH2 CH2CN
D) (CH3 )2NCH2 CH2 Br
E) all of the above
60)
61) Consider the alcohol 3-methylpentan-3-ol. Is this alcohol primary, secondary, or tertiary?
61)
62) Give the IUPAC name for (CH3)2 CCHCH2 CH2OH.
62)
63) In a 1-butanol molecule, what part of the molecule is described as hydrophilic?
63)
64) In a 1-butanol molecule, what part of the molecule is described as hydrophobic?
64)
65) Which of the compounds below has a pKa that most closely matches the pKa of ethanol?
A) ammonia
B) acetic acid
C) water
D) phenol
E) HCl
65)
66) What gaseous byproduct is evolved when sodium metal is added to ethanol?
66)
67) Which of the following reagents or sequences do not produce an alcohol or diol from an alkene
starting material?
A) OsO4 , H2 O2
B) HCO3 H
C) H+, H2O
D) Hg(OAc)2 , H2 O followed by NaBH4
E) BH3.THF followed by H2 O2 , NaOH
67)
68) Which of the following terms best describes the reactive nature of a Grignard reagent?
A) carbene
B) free radical
C) carbocation
D) electrophile
E) nucleophile
68)
69) Name the major organic product which results when CH3 CO2 CH2CH3 is treated with 2
equivalents of (CH3 )2CHMgBr followed by protonation with dilute acid?
69)
70) When a ketone is treated with LiAlH4 followed by addition of H2 O, what general class of product
results?
A) ether
B) secondary alcohol
C) primary alcohol
D) tertiary alcohol
E) aldehyde
70)
71) When an aldehyde is treated with LiAlH4 followed by addition of H2 O, what general class of
product results?
A) ether
B) secondary alcohol
C) primary alcohol
D) ketone
E) tertiary alcohol
71)
72) In addition to the use of complex metal hydrides, what other reaction can be used to
reduce aldehydes and ketones to alcohols?
72)
73) Provide the IUPAC name for the compound below.
73)
74) Arrange the following alcohols in order of increasing boiling point:
74)
(CH3 )3COH, CH3 (CH2 )4 OH, (CH3)3 CCH2 OH, and (CH3 )2 CHCH2 CH2OH.
75) Provide the major organic product of the following reaction.
75)
76)
77) Explain why the synthetic route shown below would be unsuccessful.
77)
78)
79)
80)
81) What Grignard reagent and carbonyl compound could be used to prepare
1-ethylcyclohexanol?
81)
10
82) Provide the reagents necessary to carry out the multistep synthesis shown below.
82)
83) Provide the IUPAC name for the following compound.
83)
84) Provide an acceptable name for the following compound.
84)
85) Provide the name of the major organic product that results when 1-pentene is treated with
aqueous acid.
85)
86) Provide the name of the major organic product that results when 1-pentene is subjected to
hydroboration/oxidation.
86)
87) What sequence of reagents is needed to convert 2-chlorobutane into 3-methyl-4-heptanol?
87)
88) What sequence of reagents is needed to convert benzyl bromide into 1-phenyl-2-octanol?
88)
89) The reaction of what two compounds produces n-butyllithium?
89)
90) Reaction of ethylmagnesium bromide with which of the following compounds yields a tertiary
alcohol after quenching with aqueous acid?
A) H2CO
B) CH3 CHO
C) ethylene oxide
D) n-butyllithium
E) (CH3 )2CO
11
90)
91) Reaction of ethylmagnesium bromide with which of the following compounds yields a secondary
A) (CH3 )2CO
91)
B) n-butyllithium
C) H2CO
D) CH3 CHO
E) ethylene oxide
92) Reaction of ethylmagnesium bromide with which of the following compounds yields a primary
A) ethylene oxide
B) CH3 CHO
C) ethyl acetate
D) (CH3 )2CO
E) n-butyllithium
93) Complete the following synthesis by providing the necessary sequence of reactants.
12
93)
92)
94) Which of the following reactions will result in the formation of a secondary alcohol(s) in good
yield?
A)
B)
C)
D)
E) both A and D
13
94)
95) Which of the following substrates will not form a Grignard reagent when treated with
Mg/diethylether?
A)
95)
B)
C)
D)
E)
96) Provide a detailed step-by-step mechanism that would account for the formation of the
product in the following reaction.
96)
97) Reduction of a ketone with NaBH4 will result in the formation of -A) a secondary alcohol
B) an alkene
C) an aldehyde
D) a primary alcohol
E) an alkane
14
97)
98) Which series of reactions would best facilitate the following conversion?
A) 1. NaBH4
2. HBr (g)
3. Mg/ether
4. H2O/H3O+
B) 1. KMnO4 (aq)
2. Hg(OAc)2 (aq)
3. NaBH4 /OHC) 1. H3C-MgBr
2. H2O/H3O+
D) 1. Raney nickel
2. H3C-MgBr
3. H2O/H3O+
E) 1. NaBH4
2. H3PO4 /
15
98)
Answer Key
Testname: UNTITLED3
1) Methanol or methyl alcohol

ID: oc6w 10-1
Diff: 1
2) Isopropyl alcohol or Propan-2-ol

ID: oc6w 10-2
Diff: 1
3) Ethylene glycol or Ethane-1,2-diol

ID: oc6w 10-3
Diff: 1
4) A
ID: oc6w 10-4
Diff: 2
5) A
ID: oc6w 10-5
Diff: 2
6)
ID: oc6w 10-6

Diff: 3
7)
ID: oc6w 10-7

Diff: 1
8)
ID: oc6w 10-8

Diff: 3
9) (CH3 )2CHCH2 CH2 CH2 OH

ID: oc6w 10-9
Diff: 1
10)
ID: oc6w 10-10

Diff: 2
16
Answer Key
Testname: UNTITLED3
11) 1. BH3 THF
2. H2 O2 , NaOH
ID: oc6w 10-11
Diff: 3
12) 1. LiAlH4
2. H3 O+
ID: oc6w 10-12
Diff: 1
13) B
ID: oc6w 10-13
Diff: 1
14) B
ID: oc6w 10-14
Diff: 1
15) C
ID: oc6w 10-15
Diff: 2
16) cis-3-chlorocyclohexan-1-ol
ID: oc6w 10-16
Diff: 3
17) 4-bromo-2-propylhexan-1-ol
ID: oc6w 10-17
Diff: 3
18) 3-methylcyclopent-3-en-1-ol
ID: oc6w 10-18
Diff: 2
19) (E)-4-chloro-3-methylpent-3-en-1-ol
ID: oc6w 10-19
Diff: 3
20) ethylene glycol or ethane-1,2-diol

ID: oc6w 10-20
Diff: 1
21) isobutyl alcohol or 2-methylpropan-1-ol

ID: oc6w 10-21
Diff: 1
22) cis-cyclopentane-1,3-diol
ID: oc6w 10-22
Diff: 2
23) meta-propylphenol or 3-propylphenol

ID: oc6w 10-23
Diff: 2
24) hydroquinone or benzene-1,4-diol or 1,4-dihydroxybenzene

ID: oc6w 10-24
Diff: 2
25) (Z)-4-methylhex-3-ene-1-thiol
ID: oc6w 10-25
Diff: 3
17
Answer Key
Testname: UNTITLED3
26) Butan-1-ol is more soluble in water. Decan-1-ol's larger alkyl group makes this compound more hydrophobic which
leads to increased disruption of the dipole-dipole attractions (hydrogen bonding) among neighboring water
molecules.
ID: oc6w 10-26
Diff: 2
27) Hydrogen bonding

ID: oc6w 10-27
Diff: 1
28) azeotrope
ID: oc6w 10-28
Diff: 2
29) denatured
ID: oc6w 10-29
Diff: 2
30) 1. CH3 CH2 MgBr

2. H3 O+
ID: oc6w 10-30
Diff: 2
31) 1. CH3 CH2 MgBr (2 equivalents)

2. H3 O+
ID: oc6w 10-31
Diff: 2
32) 1. Mg, Et2O

2. ethylene oxide (oxirane)
3. H3 O+
ID: oc6w 10-32
Diff: 3
33) 1. Mg, Et2O

2. D2O
ID: oc6w 10-33
Diff: 2
34) 1. BH3
2. H2 O2 , - OH
ID: oc6w 10-34
Diff: 2
35) 1. LiAlH4
2. H3 O+
ID: oc6w 10-35
Diff: 1
36) 1. O3; CH3 SCH3 or hot KMnO4, - OH

2. PhMgBr
3. H3 O+
ID: oc6w 10-36
Diff: 3
37) CH3 CH2OH + NH2 -, reactants are favored at equilibrium

ID: oc6w 10-37
Diff: 2
18
Answer Key
Testname: UNTITLED3
38) CH3 OH + Cl- , products are favored at equilibrium
ID: oc6w 10-38
Diff: 2
39) The phenoxide ion is highly stabilized relative to methoxide through resonance delocalization of the negative charge
into the aromatic ring. This stabilization makes phenoxide less reactive and a weaker base. The weaker the base, the
stronger its conjugate acid.
ID: oc6w 10-39

Diff: 3
40) 4-nitrophenol
ID: oc6w 10-40
Diff: 2
41) 2-fluorocyclohexan-1-ol
ID: oc6w 10-41
Diff: 2
42) Dissolve the mixture in an organic solvent, like ether. Place the ethereal solution into a separatory funnel. Pour an
aqueous solution of NaOH into the separatory funnel as well. The phenol will be deprotonated by the NaOH, become
the phenoxide, and dissolve in the aqueous layer. The two layers are then easily separated. The phenol can be
recovered from the aqueous layer by acidifying it and filtering.
ID: oc6w 10-42
Diff: 2
43) 1. BH3
2. H2 O2 , NaOH
ID: oc6w 10-43
Diff: 2
44) 1. HCO3H
2. H3 O+
ID: oc6w 10-44
Diff: 2
45) 1. Hg(OAc)2 , H2 O
2. NaBH4
ID: oc6w 10-45
Diff: 2
46)
ID: oc6w 10-46

Diff: 2
19
Answer Key
Testname: UNTITLED3
47)
ID: oc6w 10-47

Diff: 2
48)
ID: oc6w 10-48

Diff: 2
49) CH3 CH2CH2 CH(OH)CH(CH3 )2

ID: oc6w 10-49
Diff: 2
50)
ID: oc6w 10-50

Diff: 2
51)
ID: oc6w 10-51

Diff: 2
52) Unsuccessful. The Grignard would deprotonate the hydroxyl group instead of reacting at the carbonyl.
ID: oc6w 10-52
Diff: 2
53) One cannot form a Grignard reagent from a halide molecule containing an SH group. The acidity of the sulfhydryl
hydrogen precludes this.
ID: oc6w 10-53
Diff: 2
54)
ID: oc6w 10-54

Diff: 3
20
Answer Key
Testname: UNTITLED3
55) Ethers provide a polar, aprotic environment in which these species can form. The polar nature of these reagents
demands a polar solvent be used to facilitate their formation. Additionally, ethers are unreactive toward strong bases
and have no functional groups that react with nucleophiles.
ID: oc6w 10-55
Diff: 2
56) (CH3 )2CHCH2 CH2 CH3

ID: oc6w 10-56
Diff: 2
57) 1. Li
2. 1/2 CuI
3. CH3 CH2 I
ID: oc6w 10-57
Diff: 2
58)
ID: oc6w 10-58

Diff: 2
59)
ID: oc6w 10-59

Diff: 2
60) D
ID: oc6w 10-60
Diff: 2
61) tertiary
ID: oc6w 10-61
Diff: 1
62) 4-methylpent-3-en-1-ol
ID: oc6w 10-62
Diff: 2
63) the -OH or hydroxyl group

ID: oc6w 10-63
Diff: 1
64) the CH3 CH2 CH2CH2 - or butyl group

ID: oc6w 10-64
Diff: 1
65) C
ID: oc6w 10-65
Diff: 2
66) H2, molecular hydrogen

ID: oc6w 10-66
Diff: 2
21
Answer Key
Testname: UNTITLED3
67) B
ID: oc6w 10-67
Diff: 1
68) E
ID: oc6w 10-68
Diff: 1
69) 2,3,4-trimethylpent-3-ol
ID: oc6w 10-69
Diff: 3
70) B
ID: oc6w 10-70
Diff: 1
71) C
ID: oc6w 10-71
Diff: 1
72) catalytic hydrogenation (H2 , Raney Ni)

ID: oc6w 10-72
Diff: 2
73) 3,4,5-triethyloctan-3-ol
ID: oc6w 10-73
Diff: 2
74) (CH3 )3COH < (CH3 )3 CCH2 OH < (CH3)2 CHCH2 CH2 OH < CH3 (CH2 )4 OH
ID: oc6w 10-74
Diff: 2
75)
ID: oc6w 10-75

Diff: 2
76)
ID: oc6w 10-76

Diff: 2
77) The tertiary bromide is too hindered to undergo an SN2 reaction with hydroxide. However, the hydroxide is a strong
base and would react with the bromide above to yield an alkene via an E2 mechanism.
ID: oc6w 10-77
Diff: 2
22
Answer Key
Testname: UNTITLED3
78)
ID: oc6w 10-78

Diff: 3
79)
ID: oc6w 10-79

Diff: 2
80)
ID: oc6w 10-80

Diff: 2
81)
ID: oc6w 10-81

Diff: 1
82) 1. Mg
2. ethylene oxide
3. H3O+
ID: oc6w 10-82
Diff: 2
83) (E)-4,5,5-trimethyl-3-hexen-1-ol or (E)-4,5,5-trimethylhex-3-en-1-ol

ID: oc6w 10-83
Diff: 2
23
Answer Key
Testname: UNTITLED3
84) benzene-1,3-diol or resorcinol

ID: oc6w 10-84
Diff: 2
85) 2-pentanol
ID: oc6w 10-85
Diff: 2
86) 1-pentanol
ID: oc6w 10-86
Diff: 2
87) 1.
2.
3.
Mg, ether
CH3 CH2CH2 CHO
H+, H2O
ID: oc6w 10-87

Diff: 2
88) 1.
2.
3.
Mg, ether
CH3 (CH2)5 CHO
H+, H2O
ID: oc6w 10-88

Diff: 2
89) 1-bromobutane and lithium

ID: oc6w 10-89
Diff: 2
90) E
ID: oc6w 10-90
Diff: 2
91) D
ID: oc6w 10-91
Diff: 2
92) A
ID: oc6w 10-92
Diff: 2
93) 1) Br2, h
2) Mg, ether
3) acetaldehyde (CH3 CHO)
ID: oc6w 10-93

Diff: 3
94) E
ID: oc6w 10-94
Diff: 2
95) C
ID: oc6w 10-95
Diff: 2
24
Answer Key
Testname: UNTITLED3
96)
ID: oc6w 10-96

Diff: 2
97) A
ID: oc6w 10-97
Diff: 1
98) E
ID: oc6w 10-98
Diff: 3
25

Exam I - Practice II

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QOI 0809 OH #1

2) __________ is dissolved in water to make the solution sold commercially as rubbing

3) __________, commonly used in automobile antifreezes, is a diol which is highly toxic if

14) 1-Methylcyclopentan-1-ol is classified as __________.

15) 2-Methylpentan-3-ol is classified as __________.

17) Provide an acceptable name for the compound below.

18) Provide an acceptable name for the compound below.

19) Provide an acceptable name for the compound below.

20) Provide an acceptable name for the compound below.

23) Provide an acceptable name for the compound below.

24) Provide an acceptable name for the compound below.

25) Provide an acceptable name for the compound below.

26) Which is more soluble in water, butan-1-ol or decan-1-ol? Explain briefly.

33) Provide the reagents necessary to accomplish the following transformation.

34) Provide the reagents necessary to accomplish the following transformation.

62) Give the IUPAC name for (CH3)2 CCHCH2 CH2OH.

63) In a 1-butanol molecule, what part of the molecule is described as hydrophilic?

64) In a 1-butanol molecule, what part of the molecule is described as hydrophobic?

73) Provide the IUPAC name for the compound below.

74) Arrange the following alcohols in order of increasing boiling point:

76) Provide the major organic product of the following reaction.

78) Provide the major organic product of the following reaction.

79) Provide the major organic product of the following reaction.

80) Provide the major organic product of the following reaction.

83) Provide the IUPAC name for the following compound.

84) Provide an acceptable name for the following compound.

87) What sequence of reagents is needed to convert 2-chlorobutane into 3-methyl-4-heptanol?

89) The reaction of what two compounds produces n-butyllithium?

1) Methanol or methyl alcohol

2) Isopropyl alcohol or Propan-2-ol

3) Ethylene glycol or Ethane-1,2-diol

ID: oc6w 10-6

ID: oc6w 10-7

ID: oc6w 10-8

9) (CH3 )2CHCH2 CH2 CH2 OH

ID: oc6w 10-10

20) ethylene glycol or ethane-1,2-diol

21) isobutyl alcohol or 2-methylpropan-1-ol

23) meta-propylphenol or 3-propylphenol

24) hydroquinone or benzene-1,4-diol or 1,4-dihydroxybenzene

27) Hydrogen bonding

30) 1. CH3 CH2 MgBr

31) 1. CH3 CH2 MgBr (2 equivalents)

32) 1. Mg, Et2O

33) 1. Mg, Et2O

36) 1. O3; CH3 SCH3 or hot KMnO4, - OH

37) CH3 CH2OH + NH2 -, reactants are favored at equilibrium

ID: oc6w 10-39

ID: oc6w 10-46

ID: oc6w 10-47

ID: oc6w 10-48

49) CH3 CH2CH2 CH(OH)CH(CH3 )2

ID: oc6w 10-50

ID: oc6w 10-51

ID: oc6w 10-54

56) (CH3 )2CHCH2 CH2 CH3

ID: oc6w 10-58

ID: oc6w 10-59

63) the -OH or hydroxyl group

64) the CH3 CH2 CH2CH2 - or butyl group

66) H2, molecular hydrogen

72) catalytic hydrogenation (H2 , Raney Ni)

ID: oc6w 10-75

ID: oc6w 10-76