ch13 final tb klein1e - chemconnections

Chapter Thirteen

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy

1. What is the IUPAC name for the following compound?

CH3CHCHCHCHCH3

OH

CH3

CH3

CH3

A) 4-isopropyl-3,4-dimethyl-2-butanol B) 2,3,4-trimethyl-4-pentanol C) 1,1,2,3-tetramethyl-4-pentanol D) 3,4,5-trimethyl-2-hexanol E) 3,4,5,5-tetramethyl-2-pentanol

Ans: D Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy

2. What is the IUPAC name for isobutyl alcohol? A) 2-methyl-1-propanol B) 2-methyl-1-butanol C) 1-methyl-1-propanol D) 1,1-dimethyl-1-ethanol E) 3-methyl-1-propanol

Ans: A Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy

3.

What is the IUPAC name for the following compound?

CH3CH2CCH2CH3

CH2CH3

OH A) 1,1,1-triethylmethanol B) 1,1-diethyl-1-propanol C) 2-ethyl-3-pentanol D) 3-ethyl-3-pentanol E) t-heptanol

Ans: D Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium

4.

What is the IUPAC name for t-butyl alcohol?

A) 1-butanol B) 2-methyl-1-propanol C) 2-methyl-2-propanol D) 2-butanol E) 1,1-dimethyl-1-ethanol

Ans: C Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium


OH

A) 1-isopropyl-4-cyclopentanol B) 3-isopropyl-1-cyclopentanol C) 1-isopropyl-3-cyclopentanol D) 1-isopropyl-4-hydroxycyclopentane E) None of these

Ans: B Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium

6. What is the correct structure for 1-chloro-3-ethyl-2-pentanol?

CH3CH2CCH2CH2Cl

CH2CH3

OH

CH3CHCHCH2CH2Cl

CH2CH3

OH

CH3CH2CHCHCH2Cl

CH2CH3

OH

CH3CH2CHCH2CHCl

CH2CH3

OHI II III IV

A) I B) II C) III D) IV E) None of these

Ans: D Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium


Br

HO

A) 2-methyl-5-bromocyclohexanol B) 3-bromo-2-methylcyclohexanol C) 1-bromo-4-methylcyclohexanol D) 4-bromo-6-methylcyclohexanol E) 4-bromo-2-methylcyclohexanol

Ans: E Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard


CH3CH2C=CCH2CH3

CH3

CH2CH2OH

A) 3-methyl-4-ethyl-3-hexen-6-ol B) 4-ethyl-3-methyl-3,6-hexenol C) 3-ethyl-4-methyl-3-hexen-1-ol D) 3-methyl-4-(2-hydroxyethyl)-3-hexene E) 3-(2-hydroxyethyl)- 3-methyl-3-hexene

Ans: C Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard

9. What is the IUPAC name for the following compound? OH

A) 4-penten-2-methyl-2-ol B) 4-methyl-1-penten-2-ol C) 2-methyl-4-penten-2-ol D) 4-methyl-1-penten-4-ol E) 4-hydroxy-4-methyl-1-pentene

Ans: C Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard

10. What is the IUPAC name for the following compound? CH3

C

HOH

CCCH

2 CH3

A) (R)-3-hexyn-2-ol B) (S)-3-hexyn-2-ol C) (R)-2-hexyn-4-ol D) (S)-2-hexyn-4-ol E) (S)-2-hydroxy-3-hexyne

Ans: B

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium

11. What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?

OH

Br

Br

OH

Br Br

Br

Br

OH

CH3CH2CH2CH2CCH(CH3)OH

Br

Br

II

IV V

I

CH3CCH2CH2CH2CHOH

Br

Br

CH3

III

A) I B) II C) III D) IV E) V

Ans: D Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard

12. What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?

VIV

III

HO

HO

OH

OH

III

OH


Ans: E



OH Ans: 7-ethyl-8-methyl-4-nonanol

Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard


HO

Ans: (R)-3-ethyl-2-methyl-3-heptanol


15. What is the IUPAC name for the following compound? H Br

CH3

OH

Ans: (1R,2S)-2-bromo-1-methylcyclopentanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard


Ans: 7-cyclohexyl-2,8-dimethyl-3-decanol


17. Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol? Ans:

OH


18. Provide the structure for 5-chloro-2-propyl-1-heptanol. Ans: Cl

OH Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard

19. Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol. Ans:

OH



OH

Ans: 4-isobutyl-2-methyl-3-octanol



CC

CCH3(CH2)4

HO H

H Ans: (S)-1-octyn-3-ol



HO

Ans: 4,5,6-tripropyl-4-decanol



HO

Ans: 3-ethyl-3-cyclohexen-1-ol


24. What is the IUPAC name for the following compound? HOCH2CH2CH2OH

A) 1,2-butanediol B) isopropanol C) 1-propanol D) 1,3-propanediol E) 1,2-ethanediol

Ans: D Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard


OH

A) cis-1,2-cyclopentanediol B) meso-1,2-cyclopentanediol C) (1R,2R)-1,2-cyclopentanediol D) (1R,2S)-1,2-cyclopentanediol E) (1S,2S)-1,2-cyclopentanediol

Ans: E Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard


OH OH

Ans: 3,5-dimethyl-2,4-heptanediol


27. Provide the structure for (2R, 3S) 2-bromo-1,3-pentanediol.

Ans:

OH

OH

Br Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Hard

28.

Explain why cyclohexanol has a pKa of 18 and phenol has a pKa of 10. Use structural drawings to explain your reasoning. Ans: The conjugate base of phenol is resonance stabilized. The negative charge on

oxygen is delocalized over the aromatic ring. This makes the conjugate base more stable and thus a weaker base, making phenol a stronger acid.

O O O O

The conjugate base of cyclohexanol has no resonance stabilization and the negative charge on oxygen is localized, making it a stronger base, and cyclohexanol a weaker acid

O

Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium

29.

Rank the following alcohols in decreasing order of acidity. OH

Br

OH

F

OH

II II III

Ans: II>I>III Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium

30.

Which one of the following alcohols is most acidic? O

OH

O

OH

OH

I II III Ans: I


31.

Rank the following alcohols in decreasing order of acidity. Explain your answer.

FOH F

OHOH

IIIIII

F F

Ans: I>III>II

The negative charge on the conjugate base of compound I is stabilized by three electron withdrawing fluorine atoms via inductive effect, making it the weakest base and the alcohol strongest acid. The negative charge on the conjugate base of compound II is not stabilized, as it does not have any electronegative atoms on the carbon chain, making it a stronger base and the alcohol weakest acid. The negative charge on the conjugate base of compound III is less stabilized than I, because it has only one fluorine atom connected. Thus making it a stronger acid than II, but a weaker acid than I.


32.

Rank the following alcohols in decreasing order of acidity.

O2N OH NC OHOHI II III

Ans: I>III>II Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium

33.

Predict the product(s) for the following reaction. OH Na

Ans: ONa

+ H212


34.

Predict the product for the following reaction. OH 1. NaH

2. CH3CH2Br

Ans: O

Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium

35. Provide the reagents necessary to carry out the following conversion.

CH3CH2CH2CHCH3

Br

CH3CH2CH2CH2CH2OH

Ans: 1. (CH3)3COK 2. BH3 3. H2O2/NaOH/H2O


36. Predict the product(s) for the following reaction.

1. BH3

2. H2O2/NaOH/H2O

OH OH

OHCH2OH

I IIIII IV+ enantiomer + enantiomer


Ans: B Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium

37. Predict the product for the following reaction.

1. Hg(OAc)2, H2O

2. NaBH4

OH

OH

OH CH2OH

I II III IV


Ans: C Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium

38. Provide the reagents necessary to carry out the following conversion. (E)-3-methyl-3-hexene 3-methyl-3-hexanol

Ans: H3O+

OR 1. Hg(OAc)2, H2O 2. NaBH4


39. Predict the major product for the following reaction.

H3O+

Ans: OH



1. Hg(OAc)2, H2O

2. NaBD4

OH

OH D

OH D

OH

D OH

I II III IV V


Ans: C Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium

41. Provide the reagents necessary to carry out the following conversion. Br OH

Ans: NaOH

Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Hard

42. Provide the reagents necessary to carry out the following conversion. OH

Cl

A) NaOH/H2O B) 1. NaOCH3, 2. H3O+

C) 1. (CH3)3COK, 2. BH3, 3. H2O2/NaOH/H2O D) 1. (CH3)3COK, 2. H3O+ E) B & D

Ans: D Topic: Oxidation states Section: 13.4 Difficulty Level: Easy

43. What is the oxidation state of the carbon atoms I and II in the following reaction?

I

O

O

H

II

A) I. +1, II. +2 B) I. +2, II. +2 C) I. +1, II. +3 D) I. +3, II. +2 E) I. +2, II. +1

Ans: E Topic: Oxidation states Section: 13.4 Difficulty Level: Easy

44. What is the oxidation state of the carbon atoms I and II in the following reaction?

CH3CH

O

CH3COH

O

I II

A) I. +1, II. +2 B) I. +2, II. +2 C) I. +1, II. +3 D) I. +3, II. +2 E) I. +2, II. +1

Ans: C

Topic: Oxidation states Section: 13.4 Difficulty Level: Medium

45. For the following conversion, identify if the starting material has been oxidized, reduced or neither. Explain your answer.

OH O

Ans: Oxidized. The carbon atom in starting compound has a zero oxidation state and the carbon atom in the product has an oxidation state of +2.

Topic: Oxidation states Section: 13.4 Difficulty Level: Medium

46. For the following conversion, identify if the starting material has been oxidized, reduced or neither.

Cl

Cl

Ans: Oxidized. Topic: Oxidation states Section: 13.4 Difficulty Level: Medium

47. For the following conversion, identify if the starting material has been oxidized, reduced or neither. Explain your answer.

OH O

Ans: Neither. The oxidation state of the carbon atoms is not changed.

Topic: Oxidation states Section: 13.4 Difficulty Level: Hard

48. For the following conversion, identify if the starting material has been oxidized, reduced or neither.

O

O

H

A) reduced B) oxidized C) neither D) A & B

Ans: B Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Easy


CH3CCH2CH2CH3

O

NaBH4/CH3OH

Ans:

CH3CHCH2CH2CH3

OH



H

O

NaBH4/CH3OH

OH OHOH

O

OH

OH

I II IIIIV

A) I B) II C) III D) IV

Ans: A


51. Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4 followed by water?

O

H

O

H

O O

O

I II III

IV V A) I B) II C) III D) IV E) V

Ans: A Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard


HC CCH2CH2CH3 CH3CHCH2CH2CH3

OH

Ans: 1. H3O+/ HgSO4 2. NaBH4/CH3OH



H

O

H2.Pd

OH OHOH

O

OH

OH

I II III IV A) I B) II C) III D) IV

Ans: C Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard


COCH3

O

O

NaBH4 / H2O

Ans:

COCH3

O

H

HO Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard


COCH3

O

O

1. LiAlH4

2. H2O

excess

Ans: CH2OH

H

HO Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard


HgSO4

H2O / H2SO4NaBH4/CH3OH

Ans:

OH


57. Provide the reactant (A) for the following reaction 1. LiAlH4

2. H2O5-methyl-3-heptanolA

O

H

O

H

O O

O

I IIIII

IV V A) I B) II C) III D) IV E) V

Ans: A Topic: Preparation of Diols Section: 13.5 Difficulty Level: Easy

58. Provide the reagents necessary to carry out the following conversion. cyclohexene cis-1,2-cyclohexanediol

A) KMnO4, NaOH, Η2Ο B) KMnO4, H3O+, 75oC C) H2SO4, heat D) 1. mCPBA 2. H3O+

E) none of these Ans: A

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium

59. Predict the product(s) for the following reaction sequence.

3-hexyne

H2/Ni2B 1. OsO42. NaHSO3

HO

H OH

HHO

HO H

H H

HO OH

HI II III

A) I B) II C) III D) Both I & II E) None of these

Ans: B Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium

60. Provide the reagents necessary to carry out the following conversion. cyclohexene trans-1,2-cyclohexanediol

A) KMnO4, NaOH, Η2Ο B) KMnO4, H3O+, 75oC C) H2SO4, heat D) 1. mCPBA 2. H3O+

E) none of these Ans: D

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium

61. Provide the structure(s) of the product(s) in the following reaction sequence.

ACH3CH2ONa

B Br2

hν

mCPBA NaOH/H2OC D

Ans:

Br

O

CH3 CH3

OH

OH

HA B C D+ enantiomer+ enantiomer

Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard


NaBH4/CH3OH

O

H

O

excess

OH

H

O O

OH

OH

OH

OH

OH

OH

III III

IV

OH

OH

V


Ans: C Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium


OH3O

+

OH OH

OH

OH

OH

O

H

I II III IV

A) I B) II C) III D) IV E) none of these

Ans: C Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium

64. Provide the reagent(s) necessary to carry out the following conversion.

OH

OH

Ans: 1. mCPBA 2. H3O+ OR NaOH/H2O



OH

OH

Ans: 1. O3 2. (CH3)2S 3. excess NaBH4/CH3OH



O

O

2. H2O

1. excess LiAlH4

O

Ans: OH

OH

OH Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Easy

67. Predict the product for the following reaction sequence. O

2. H2O

1. CH3CH2MgBr

Ans: HO


68. Predict the product for the following reaction sequence.

BrH

O

Mg/ether

2. H2O

1.

Ans:

OH Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Medium


COCH3

O

OH

Ans: 1. excess CH3MgBr/ether 2. H2O



1. CH3CH2CH2MgBr/ether

2. H2O

O

OH

HO

I II

OH

IVIIIOH


Ans: A Topic: Preparation of Alcohols Section: 13.6 Difficulty Level: Medium

71. Predict the product for the following reaction. Br

Mg/ether H H

O

1.

2. H2O

Ans: OH


72. Provide the reagent(s) necessary to carry out the following conversion. HO

Ans: 1. HBr 2. Mg/ether

3. H H

O

4. H2O


73. Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction.

Ans: OMgBr

1.

2. H2O Topic: Preparation of alcohols Section: 13.6 Difficulty Level: Medium


OCH3

O

2. H2O

1. CH3CH2CH2MgBrexcess

Ans:

OH

Topic: Protection of alcohols Section: 13.7 Difficulty Level: Hard

75. Provide the reagent(s) necessary to carry out the following conversion. HO Br HO

OH

Ans: 1. (CH3)3SiCl / (CH3CH2)3N 2. Mg/ether

3.

O

4. H2O 5. TBAF

Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium


Br

OH

A B

O

CTBAF

D (CH3)3SiCl

(CH3CH2)3N

Mg/ ether

1.

2. H2O

Ans: OSi(CH3)3

Br

OSi(CH3)3

MgBr

A B OSi(CH3)3

HO

C

OH

HO

D Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium


Br

OH

H H

O

TBAF (CH3)3SiCl

(CH3CH2)3N

Mg/ ether

1.

2. H2O

A) 2,4-heptanediol B) 1,4-heptanediol C) 2,5-octanediol D) 1,5-octanediol E) none of these

Ans: B Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium


HO HO

Ans: 1. (CH3)3SiCl / (CH3CH2)3N 2. NaNH2 3. CH3CH2CH2Br 4. TBAF

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy

79. Which of the following could be used to synthesize 1-bromopentane?

A) CH3CH2CH2CH=CH2 + HBr ⎯⎯⎯⎯→ B) CH3CH2CH2CH2CH2OH + PBr3 ⎯⎯⎯⎯→ C) CH3CH2CH2CH2CH2OH + NaBr ⎯⎯⎯⎯→ D) CH3CH2CH2CH2CH2OH + Br2 ⎯⎯⎯⎯→ E) CH3CH2CH2CH=CH2 + Br2 ⎯⎯⎯⎯→

Ans: B Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy

80. Provide the reagents necessary to convert 3-methyl-2-butanol to 2-bromo-3-methylbutane.

A) conc. HBr B) Br2 C) NaBr, H2SO4 D) PBr3 E) HBr, peroxide

Ans: D Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium

81. Predict the product for the following reaction. OH

PBr3

Ans: Br

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard

82. Predict the major product for the following reaction and provide a curved arrow mechanism for the formation of the product.

OH

HBr

Ans:

Br Mechanism

OH H Br OH2

+ Br

H

Br

Br



OH

HCl

Ans:

Cl

Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium


SOCl2/pyridine

OH Ans:

Cl Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium

85. Predict the major product for the following reaction. H

H

OH

CH3

1. TsCl /pyridine

2. NaI

H

H

I

CH3

H

H

OTsI

CH3

I

H

H

CH3

H

H

Ts

CH3

I II III IV

A) I B) II C) III D) IV E) both I and III

Ans: C Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium

86. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium bromide.

A) trans-1-bromo-3-methylcyclopentane B) cis-1-bromo-3-methylcyclopentane C) 1-methylcyclopentene D) 2-Methylcyclopentene E) 3-Methylcyclopentene

Ans: A Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium

87. The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene goes via_____.

A) SN1 mechanism B) SN2 mechanism C) E1 mechanism D) E2 mechanism E) None of these.


88. Explain why the following reaction will not produce alcohol as product.

Cl

NaOHOH

Ans: The tertiary halide is too sterically hindered for an SN2 reaction with hydroxide as

nucleophile. Instead, the hydroxide ion is a strong base and will react with the alkyl chloride to form alkene via an E2 mechanism.



OH 1. TsCl/pyridine

2. CH3CH2ONa

Ans:


90. Predict the major product for the following reaction. OH

H2SO4

Δ Ans:


91. Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane. . Ans: 1. H2SO4, heat

2. H2/Pd OR 1. TsCl/pyridine 2. CH3CH2ONa 3. H2/Pd


92. Provide a stepwise curved arrow mechanism for the following reaction. HO

CH2CH3

CH2CH3 H2SO4Δ

CH2CH3

CH2CH3

Ans:

CH2CH3

HOCH2CH3

H O S O H

O

O

CH2CH3

H2O CH2CH3

O S O H

O

O

+

CH2CH3

H3CH2C

CH2CH3

CH2CH3

CH2CH3

CH2CH3

CH2CH3

H3CH2C H

O S O H

O

O

+ H2SO4

+ H2O


93. Predict the product and provide a stepwise curved arrow mechanism for the following reaction.

H2SO4heat

OH

OH

Ans:

O

Mechanism

OH H O S O H

O

O

O S O H

O

O

+

OH

OHOH2

OH

HO S O H

O

O

O HO

+ H2SO4+ H2O


94. Predict the product for the following reaction. PCC

2-hexanolCH2Cl2

A)

CH3COH

O

B)

CH3CH2CH2CH2COH

O

C)

CH3(CH2)3CCH3

O

D)

CH3CH2CH2CH2CH2COH

O

E)

CH3CH2CH2CH2CH2CH

O

Ans: C


95. Provide the reagents necessary to carry out the following conversion. OH O

A) KMnO4/NaOH/H2O B) CrO3/H2SO4/H2O C) H2, Pt D) Br2, CCl4 E) None of these

Ans: B Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy


Na2Cr2O7/H2SO4/H2O

Ans: O



CH2Cl2

PCC

Ans: H

O



OH H

O

A) KMnO4/NaOH/H2O B) CrO3/H2SO4/H2O C) PCC/CH2Cl2 D) Br2, CCl4 E) None of these



OH OH

O

A) KMnO4/NaOH/H2O B) CrO3/H2SO4/H2O C) PCC/CH2Cl2 D) Br2, CCl4 E) None of these

Ans: B Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium


OH

CH2OH

PCC/CH2Cl2excess

Ans: OH

CH

O Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium


OH PCC

CH2Cl2

Ans: No reaction. Tertiary alcohols do not undergo oxidation reactions. Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium

102. Predict the product for the following reaction. PCC

CH2Cl2cis-4-methylcyclohexanol

Ans: O

. Topic: Synthesis Section: 13.13 Difficulty Level: Medium

103. Provide the structure for the final product (D), in the following reaction sequence.

CH3CH2CHOH

CH3

PBr3A

MgBH3C H

O

CH2O D

ether

Ans: OH

Topic: Synthesis Section: 13.13 Difficulty Level: Hard

104. Provide the structure for the final product (E), in the following reaction sequence.

OHPBr3 A

MgB C

H2OD

PCC

CH2Cl2

O

O

IV V

etherE

H H

O

OH

OHI II

H

OIII


Ans: C Topic: Synthesis Section: 13.13 Difficulty Level: Medium

105. Provide the structure for product (A), in the following reaction sequence.

PBr3

OH

Mg D2O Aether

A) CH3CH2CH2CH3 B) CH3CH2CHDCH3

C) CH3CH2CHODCH3

D) CH3CH2CH2CH2OD E) CH3CH2CH2CH2D

Ans: B Topic: Synthesis Section: 13.13 Difficulty Level: Medium


OH

O

Ans: 1. PBr3

2. Mg/ether

3. H

O

4. H2O 5. PCC/CH2Cl2


107. Provide a stepwise synthesis for the following.

Ans:

O

Cl2

1. CH3MgBr

Cl

OH

CH3CH2ONa

H2SO4

H3O+

OH

PCC

CH2Cl2hν

2. H2O heat


108. Provide the product for the following reaction sequence: MgBr

H2O

MgBr

H2O

ether

K2Cr2O7/H2SO4/H2O

ether

OH PCCCH2Cl2

OH O HO

OI II III

IV V


Ans: C Topic: Synthesis Section: 13.13 Difficulty Level: Medium

109. Predict the product, for the following reaction sequence,

OHSOCl2 H

O

CrO3/ H2SO4/H2OMg/ether

2. H3O+

1.

pyridine

A) 6,7-dimethyl-3-nonanol B) 6,7-dimethyl-3-nonanone C) 6,7-dimethyl-3-nonanal D) 3,4-dimethyl-7-nonanol E) 3,4-dimethyl-7-nonanone

Ans: B Topic: Synthesis Section: 13.13 Difficulty Level: Hard

110. Provide a stepwise synthesis for the following.

O

Ans:

Cl2 CH3CH2ONa PCC

CH2Cl2hν

1. BH3

2. H2O2/NaOH/H2O

ClOH

O


111. Provide the reagents necessary to carry out the following conversion. O

O

Ans: 1. Cl2/hν

2. CΗ3CΗ2ONa 3. KMnO4/NaOH/H2O 4. excess PCC/CH2Cl2



HO

O

HO

HO

Ans: 1. (CH3)3SiCl/ (CH3CH2)3N

2. CH3MgBr 3. H3O+

Topic: Synthesis Section: 13.13 Difficulty Level: Medium


Br OH

O

Ans: 1. NaOH

2. Na2Cr2O7/H2SO4/H2O


114. Provide a stepwise synthesis to carry out the following conversion.

Ans:

Br2

Br

CH3CH2ONa

PCC

CH2Cl2 OOH

CH3H2SO4

OH1. BH3

2. H2O2/NaOH/H2Ohν

1. CH3MgBr

2. H2O heat

H2/Pd

ch13 final tb klein1e - chemconnections

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