QOI 0809 OH #1 - UAlgw3.ualg.pt/~abrigas/QOI0809_OH_ss.pdf · QOI 0809 OH #1 Name_____ SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question

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) π C) sp D) p E) σ

4)

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)



1

9) Provide the structure of the major organic product in the reaction below.

(CH3)2CHCH2CH2CHO 1. LiAlH4

2. H3O+→

9)


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)

2

ESSAY. Write your answer in the space provided or on a separate sheet of paper.

16) Provide an acceptable name for the compound below.





HOCH2CH2OH


(CH3)2CHCH2OH


3




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 (CH3CH2CH2CH2CHO) to heptan-3-ol


methyl isobutyrate [(CH3)2CHCO2CH3] to 3-ethyl-2-methylpentan-3-ol


benzyl bromide (PhCH2Br) to 3-phenylpropan-1-ol

4

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


2-methyl-2-octene to 2-methyloctan-3-ol


methyl benzoate (PhCO2CH3) to benzyl alcohol (PhCH2OH)


37) Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors

reactants or products.

CH3CH2O- + NH3

38) Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors

reactants or products.

CH3O- + 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.

5

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.




CH3CH2CH2CHO 1. (CH3)2CHMgBr

2. H3O+→



6

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 (CH3COCl) 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. CH3CH2CH2I

→

57) Show how one might prepare 3-methylpentane by beginning with 2-iodobutane and employing the

Corey-House reaction.



7


60) Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?

A) CH3COCH2CH2Br

B) H2NCH2CH2Br

C) BrCH2CH2CH2CN

D) (CH3)2NCH2CH2Br

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)2CCHCH2CH2OH. 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, H2O2

B) HCO3H

C) H+, H2O

D) Hg(OAc)2, H2O followed by NaBH4

E) BH3.THF followed by H2O2, 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 CH3CO2CH2CH3 is treated with 2

equivalents of (CH3)2CHMgBr followed by protonation with dilute acid?

69)

8


70) When a ketone is treated with LiAlH4 followed by addition of H2O, 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 H2O, 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:

(CH3)3COH, CH3(CH2)4OH, (CH3)3CCH2OH, and (CH3)2CHCH2CH2OH.

74)

75) Provide the major organic product of the following reaction. 75)

9


77) Explain why the synthetic route shown below would be unsuccessful. 77)




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) CH3CHO

C) ethylene oxide

D) n-butyllithium

E) (CH3)2CO

90)

11

91) Reaction of ethylmagnesium bromide with which of the following compounds yields a secondary


A) (CH3)2CO

B) n-butyllithium

C) H2CO

D) CH3CHO

E) ethylene oxide

91)

92) Reaction of ethylmagnesium bromide with which of the following compounds yields a primary


A) ethylene oxide

B) CH3CHO

C) ethyl acetate

D) (CH3)2CO

E) n-butyllithium

92)


93) Complete the following synthesis by providing the necessary sequence of reactants. 93)

12


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

94)

13

95) Which of the following substrates will not form a Grignard reagent when treated with

Mg/diethylether?

A)

B)

C)

D)

E)

95)


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

97)

14

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/OH-

C) 1. H3C-MgBr

2. H2O/H3O+

D) 1. Raney nickel

2. H3C-MgBr

3. H2O/H3O+

E) 1. NaBH4

2. H3PO4/△

98)

15

Answer KeyTestname: UNTITLED3

1) Methanol or methyl alcoholID: oc6w 10-1Diff: 1

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

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

4) AID: oc6w 10-4Diff: 2

5) AID: oc6w 10-5Diff: 2

6)

ID: oc6w 10-6Diff: 3

7)


8)


9) (CH3)2CHCH2CH2CH2OH


10)


16


11) 1. BH3·THF

2. H2O2, NaOH


12) 1. LiAlH4

2. H3O+


13) BID: oc6w 10-13Diff: 1

14) BID: oc6w 10-14Diff: 1

15) CID: oc6w 10-15Diff: 2

16) cis-3-chlorocyclohexan-1-olID: oc6w 10-16Diff: 3

17) 4-bromo-2-propylhexan-1-olID: oc6w 10-17Diff: 3

18) 3-methylcyclopent-3-en-1-olID: oc6w 10-18Diff: 2

19) (E)-4-chloro-3-methylpent-3-en-1-olID: oc6w 10-19Diff: 3

20) ethylene glycol or ethane-1,2-diolID: oc6w 10-20Diff: 1

21) isobutyl alcohol or 2-methylpropan-1-olID: oc6w 10-21Diff: 1

22) cis-cyclopentane-1,3-diolID: oc6w 10-22Diff: 2

23) meta-propylphenol or 3-propylphenolID: oc6w 10-23Diff: 2

24) hydroquinone or benzene-1,4-diol or 1,4-dihydroxybenzeneID: oc6w 10-24Diff: 2

25) (Z)-4-methylhex-3-ene-1-thiolID: oc6w 10-25Diff: 3

17


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 10-26Diff: 2

27) Hydrogen bondingID: oc6w 10-27Diff: 1

28) azeotropeID: oc6w 10-28Diff: 2

29) denaturedID: oc6w 10-29Diff: 2

30) 1. CH3CH2MgBr

2. H3O+


31) 1. CH3CH2MgBr (2 equivalents)

2. H3O+


32) 1. Mg, Et2O

2. ethylene oxide (oxirane)

3. H3O+


33) 1. Mg, Et2O

2. D2O


34) 1. BH3

2. H2O2, -OH


35) 1. LiAlH4

2. H3O+


36) 1. O3; CH3SCH3 or hot KMnO4, -OH

2. PhMgBr

3. H3O+


37) CH3CH2OH + NH2-, reactants are favored at equilibrium


18


38) CH3OH + Cl-, products are favored at equilibrium


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.


40) 4-nitrophenolID: oc6w 10-40Diff: 2

41) 2-fluorocyclohexan-1-olID: oc6w 10-41Diff: 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 10-42Diff: 2

43) 1. BH3

2. H2O2, NaOH


44) 1. HCO3H

2. H3O+


45) 1. Hg(OAc)2, H2O

2. NaBH4ID: oc6w 10-45Diff: 2

46)


19


47)


48)


49) CH3CH2CH2CH(OH)CH(CH3)2ID: oc6w 10-49Diff: 2

50)


51)


52) Unsuccessful. The Grignard would deprotonate the hydroxyl group instead of reacting at the carbonyl.ID: oc6w 10-52Diff: 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 10-53Diff: 2

54)


20


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 10-55Diff: 2

56) (CH3)2CHCH2CH2CH3ID: oc6w 10-56Diff: 2

57) 1. Li

2. 1/2 CuI

3. CH3CH2I


58)


59)


60) DID: oc6w 10-60Diff: 2

61) tertiaryID: oc6w 10-61Diff: 1

62) 4-methylpent-3-en-1-olID: oc6w 10-62Diff: 2

63) the -OH or hydroxyl groupID: oc6w 10-63Diff: 1

64) the CH3CH2CH2CH2- or butyl group


65) CID: oc6w 10-65Diff: 2

66) H2, molecular hydrogen


21


67) BID: oc6w 10-67Diff: 1

68) EID: oc6w 10-68Diff: 1

69) 2,3,4-trimethylpent-3-olID: oc6w 10-69Diff: 3

70) BID: oc6w 10-70Diff: 1

71) CID: oc6w 10-71Diff: 1

72) catalytic hydrogenation (H2, Raney Ni)


73) 3,4,5-triethyloctan-3-olID: oc6w 10-73Diff: 2

74) (CH3)3COH < (CH3)3CCH2OH < (CH3)2CHCH2CH2OH < CH3(CH2)4OH


75)


76)


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 10-77Diff: 2

22


78)


79)


80)


81)


82) 1. Mg

2. ethylene oxide

3. H3O+


83) (E)-4,5,5-trimethyl-3-hexen-1-ol or (E)-4,5,5-trimethylhex-3-en-1-olID: oc6w 10-83Diff: 2

23


84) benzene-1,3-diol or resorcinolID: oc6w 10-84Diff: 2

85) 2-pentanolID: oc6w 10-85Diff: 2

86) 1-pentanolID: oc6w 10-86Diff: 2

87) 1. Mg, ether

2. CH3CH2CH2CHO

3. H+, H2O


88) 1. Mg, ether

2. CH3(CH2)5CHO

3. H+, H2O


89) 1-bromobutane and lithiumID: oc6w 10-89Diff: 2

90) EID: oc6w 10-90Diff: 2

91) DID: oc6w 10-91Diff: 2

92) AID: oc6w 10-92Diff: 2

93) 1) Br2, hν 2) Mg, ether 3) acetaldehyde (CH3CHO)


94) EID: oc6w 10-94Diff: 2

95) CID: oc6w 10-95Diff: 2

24


96)


97) AID: oc6w 10-97Diff: 1

98) EID: oc6w 10-98Diff: 3

25

Documents

QOI 0809 OH #1 - UAlgw3.ualg.pt/~abrigas/QOI0809_OH_ss.pdf · QOI 0809 OH #1 Name_____ SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question