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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

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

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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

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

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

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6. What is the correct structure for 1-chloro-3-ethyl-2-pentanol? CH₃CH₂CCH₂CH₂Cl CH2CH3 OH CH₃CHCHCH₂CH₂Cl CH2CH3 OH CH3CH2CHCHCH2Cl CH2CH3 OH CH₃CH₂CHCH₂CHCl CH2CH3 OH I II III IV A) I B) II C) III D) IV E) None of these Ans: D

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

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

Difficulty Level: Hard

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

CH3 C HO H C CCH 2CH 3 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

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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

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

V IV I II HO HO OH OH III OH A) I B) II C) III D) IV E) V Ans: E

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OH

Ans: 7-ethyl-8-methyl-4-nonanol Topic: Nomenclature of alcohols

Section: 13.1

HO

Ans: (R)-3-ethyl-2-methyl-3-heptanol Topic: Nomenclature of alcohols

Section: 13.1

OH Br

Ans: (1R,2S)-2-bromo-1-methylcyclopentanol Topic: Nomenclature of alcohols

Section: 13.1

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OH

Ans: 7-cyclohexyl-2,8-dimethyl-3-decanol Topic: Nomenclature of alcohols

Section: 13.1

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

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

OH

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OH

Ans: 4-isobutyl-2-methyl-3-octanol Topic: Nomenclature of alcohols

Section: 13.1

C C C CH3(CH2)4 HO H H Ans: (S)-1-octyn-3-ol Topic: Nomenclature of alcohols Section: 13.1

HO

Ans: 4,5,6-tripropyl-4-decanol Topic: Nomenclature of alcohols Section: 13.1

HO

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24. What is the correct structure for 2-methylphenol?

V IV I II III OH OH HO OH OH A) I B) II C) III D) IV E) V Ans: A

25. What is the correct structure for 2-bromo-5-isopropylphenol?

V IV I _II _III OH OH Br OH Br OH Br OH Br Br A) I B) II C) III D) IV E) V Ans: B

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26. What is the IUPAC name for the following compound? OH Br Br A) 3,4-dibromophenol B) 2,4-dibromophenol C) 2,5-dibromophenol D) 3,6-dibromophenol E) 2,6-dibromophenol Ans: C

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

Ans: 2-sec-butyl-5-ethylphenol Topic: Nomenclature of alcohols Section: 13.5

284. 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

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

OH OH

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

3127. Provide the structure for (2R,3S)- 2-bromo-1,3-pentanediol. Ans:

OH OH

Br

Topic: Acidity of alcohols and phenols Section: 13.2

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3228. 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

3329. Rank the following alcohols in decreasing order of acidity.

OH Br OH F OH I I II III Ans: II>I>III

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340. Which one of the following alcohols is most acidic? O OH O OH OH I II III Ans: I

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

F OH _F OH OH I II III 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.

362. Rank the following alcohols in decreasing order of acidity.

O2N OH OH NC OH

I _II III

Ans: I>III>II

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Section: 13.2

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

OH _Na

Ans: ONa

+ H1 2 2

Li OH Ans: O Li H₂ 1 2 +

394. Predict the product for the following reaction.

OH _{1. NaH}

2. CH₃CH₂Br

Ans: O

Topic: Preparation of Alcohols Section: 13.3

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3540. Provide the reagents necessary to carry out the following conversion. CH₃CH₂CH₂CHCH₃ Br CH₃CH₂CH₂CH₂CH₂OH Ans: 1. (CH3)3COK 2. BH3 3. •THF 4. H2O2/NaOH/H2O

1. BH₃ THF 2. H2O2/NaOH/H2O OH OH OH CH2OH I II III IV + enantiomer + enantiomer A) I B) II C) III D) IV E) None of these Ans: B

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4237. Predict the product for the following reaction. 1. Hg(OAc)2, H2O 2. NaBH₄ OH OH OH CH2OH I II III IV A) I B) II C) III D) IV E) None of these Ans: C

3843. 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

3944. Predict the major product for the following reaction.

H₃O+

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1. Hg(OAc)2, H2O 2. NaBD4 OH OH _D OH D OH D OH I II III IV V A) I B) II C) III D) IV E) V Ans: C

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

Br _OH

Ans: NaOH

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472. 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, •THF, 3. H2O2/NaOH/H2O D) 1. (CH3)3COK, 2. H3O+ E) B & D Ans: D

Topic: Oxidation states Section: 13.4

483. What is the oxidation state of the carbon atoms I and II in the following reactioncompound? 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

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494. 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

450. 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 bonded to OH in the starting compound has a zero oxidation state and the carbonyl carbon atom in the product has an oxidation state of +2. Topic: Oxidation states

Section: 13.4

5146. For the following conversion, identify if the starting material has been oxidized, reduced or neither.

Cl

Ans: Oxidized. Topic: Oxidation states Section: 13.4

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4752. 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

4853. 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

54. For the following conversion, identify if the starting material has been oxidized, reduced or neither. O OH O O A) reduced B) oxidized C) neither D) A & B Ans: C

Topic: Preparation of Alcohols via Reduction Section: 13.4

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CH₃CCH₂CH₂CH₃ O NaBH₄/CH₃OH Ans: CH₃CHCH₂CH₂CH₃ OH

H O NaBH4/CH3OH OH OH OH O OH OH I II III IV A) I B) II C) III D) IV Ans: A

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571. 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

HC CCH2CH2CH3 CH3CHCH2CH2CH3 OH

Ans: 1. H3O+/ HgSO4

2. NaBH4/CH3OH

OR

1. H2/Ni2B (OR Na, NH3)

2. H3O+

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593. Predict the product for the following reaction. H O H2.Pd OH OH OH O OH OH I II III IV A) I B) II C) III D) IV Ans: C

COCH3 O O NaBH4 / H2O Ans: COCH3 O H HO

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5561. Predict the product for the following reaction. COCH3 O O 1. LiAlH4 2. H2O excess Ans: CH2OH H HO

HgSO4

H₂O / H₂SO₄

NaBH₄/CH₃OH

Ans:

OH

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5763. Provide the reactant (A) for the following reaction 1. LiAlH₄ 2. H₂O 5-methyl-3-heptanol A 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 Diols Section: 13.5

5864. Provide the reagents necessary to carry out the following conversion. cyclohexene cis-1,2-cyclohexanediol

A) KMnO4, NaOHcold

B) KMnO4, H3O+, 75oC

C) H2SO4, heat

D) 1. mCPBA 2. H3O+

E) none of these Ans: A

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5965. Predict the product(s) for the following reaction sequence. 3-hexyne H2/Ni2B 1. OsO4

2. NaHSO₃ HO H _OH H HO HO _H H H HO _OH H I II III A) I B) II C) III D) Both I & II E) None of these Ans: BA

660. Provide the reagents necessary to carry out the following conversion. cyclohexene trans-1,2-cyclohexanediol A) KMnO4, NaOH B) KMnO4, H3O+, 75oC C) H2SO4, heat D) 1. mCPBA 2. H3O+ E) none of these Ans: D

671. Provide the structure(s) of the each product (A-D)(s) in the following reaction sequence.

ACH3CH2ONa B Br₂ h mCPBA NaOH/H2O C D Ans: Br O CH3 CH3 OH OH H A B C D + enantiomer + enantiomer

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NaBH₄/CH₃OH O H O excess OH H O O OH OH OH OH OH OH I II III IV OH OH V A) I B) II C) III D) IV E) V Ans: C

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693. Predict the product(s) for the following reaction. O H3O+ 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

7064. 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 4.

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O O 2. H2O 1. excess LiAlH4 O Ans: OH OH OH

Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6

6773. Predict the product for the following reaction sequence.

O

2. H₂O 1. CH₃CH₂MgBr

Ans: HO

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6874. Predict the product for the following reaction sequence. Br H O Mg/ether 2. H₂O 1. Ans: OH

OH O

O

Ans: 1. excess CH3MgBr/ether

2. H2O

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760. Predict the product for the following reaction. 1. CH3CH2CH2MgBr/ether 2. H2O O OH HO I II OH IV III OH A) I B) II C) III D) IV E) None of these Ans: A

Br Mg/ether _H _H O 1. 2. H₂O Ans: OH

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78. Using Grignard reaction, show how you could prepare the following alcohol. OH Ans: MgBr 1. 2. H₂O H C H O

79. Using Grignard reaction, show how you could prepare the following alcohol.

OH Ans: O MgBr O MgBr OR 1. 2. H₂O 2. H₂O 1.

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80. Using Grignard reaction, show how you could prepare the following alcohol. HO Ans: O MgBr OR 1. 2. H2O 2. H2O 1. MgBr O MgBr 1. 2. H2O O OR

HO Ans: 1. HBr 2. Mg/ether 3. H H O 4. H2O

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7382. Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction. Ans: O MgBr 1. 2. H₂O

Topic: Preparation of alcohols via Grignard Reagents Section: 13.6

OCH₃ O 2. H2O 1. CH3CH2CH2MgBr excess Ans: OH

2. H2O 1. CH3CH2MgBr excess O O Ans: OH OH

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85. Predict the product for the following reaction. 2. H₂O 1. CH₃CH₂MgBr excess O O O Ans: OH

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

2. H₂O 1. CH₃CH₂MgBr excess O O O Ans: OH Mechanism O O O O O CH3CH2MgBr O O O O O O CH3CH2MgBr + CH3OMgBr + CH3OMgBr O CH3CH2MgBr H O H HO + OH

Topic: Protection of alcohols Section: 13.7

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7587. 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

O HO HO OH Ans: 1. CH3)3SiCl / (CH3CH2)3N 2. MgBr 3. H2O 4. TBAF Topic: Protection of alcohols Section: 13.7

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7689. Predict the structure of each product(A-D)s) for the following reaction sequence. Br OH A B O C TBAF 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

7790. Predict the product(s) for the following reaction sequence.

Br OH H H O TBAF Mg/ ether 1. 2. H2O (CH3)3SiCl (CH3CH2)3N A) 2,4-heptanediol B) 1,4-heptanediol C) 2,5-octanediol D) 1,5-octanediol E) none of these Ans: B

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7891. Provide the reagents necessary to carry out the following conversion. HO HO Ans: 1. (CH3)3SiCl / (CH3CH2)3N 2. NaNH2 3. CH3CH2CH2Br 4. TBAF

Topic: Reactions of Alcohols Section: 13.9

7992. 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

8093. 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

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OH

PBr3

Ans: Br

8295. 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 + H2O

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8396. Predict the major product for the following reaction.

OH

HCl

Ans:

Cl

SOCl2/pyridine

OH

Ans:

Cl

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8598. Predict the major product for the following reaction. H H OH CH3 1. TsCl /pyridine 2. NaI H H I CH3 H H OTs 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

8699. 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-mMethylcyclopentene E) 3-mMethylcyclopentene Ans: A

Difficulty Level: Medium 87100

.

The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene goes via a(n) _____.

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

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.

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

Cl

NaOH

OH

not produced

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.

. Predict the major product for the following reaction.

OH _{1. TsCl/pyridine} 2. CH₃CH₂ONa

Ans:

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90103

. Predict the major product for the following reaction.OH

H2SO4



Ans:

.

Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane. . Ans: 1. H2SO4, heat 2. H2/Pd OR OR 1. TsCl/pyridine 2. CH3CH2ONa 3. H2/Pd 4.

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92105

. Provide a stepwise curved arrow mechanism for the following reaction.HO CH2CH3 CH₂CH₃ _H 2SO4  CH2CH3 CH2CH3 Ans: CH2CH3 HO CH2CH3 H O S O H O O CH2CH3 H2O _CH 2CH3 O S O H O O + CH2CH3 H3CH2C CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CH3 H3CH2C _H O S O H O O + H2SO4 + H2O

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93106

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

H₂SO₄ heat OH OH Ans: O Mechanism OH H O S O H O O O S O H O O + OH OH OH2 OH H O S O H O O O H O + H2SO4 + H₂O

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94107

. Predict the product for the following reaction.PCC 2-hexanol CH₂Cl₂ A) CH3COH O B) CH3CH2CH2CH2COH O C) CH₃(CH₂)₃CCH₃ O D) CH3CH2CH2CH2CH2COH O E) CH3CH2CH2CH2CH2CH O Ans: C

.

Provide the reagents necessary to carry out the following conversion.

OH O A) KMnO4/NaOH/H2O B) Na2Cr2CrOO73/H2SO4/H2O C) H2, Pt D) Br2, CCl4 E) None of these Ans: B

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96109

. Predict the product for the following reaction.OH Na₂Cr₂O₇/H₂SO₄/H₂O

Ans: O

Difficulty Level: Easy 97110

. Predict the product for the following reaction.OH

CH₂Cl₂ PCC

Ans: H

O

Difficulty Level: Easy 98111

.

OH _H O A) KMnO4/NaOH/H2O B) Na2Cr2O7CrO3/H2SO4/H2O C) PCC/CH2Cl2 D) Br2, CCl4 E) None of these Ans: C

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99112

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

OH _OH O A) KMnO4/NaOH/H2O B) Na2Cr2O7CrO3/H2SO4/H2O C) PCC/CH2Cl2 D) Br2, CCl4 E) None of these Ans: B

. Predict the product for the following reaction.

OH CH2OH PCC/CH2Cl2 excess Ans: OH CH O

. Predict the product for the following reaction.

OH PCC

CH₂Cl₂

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.

Predict the product for the following reaction.

PCC

cis-4-methylcyclohexanol

CH2Cl2

Ans: O

. Topic: Oxidation of Phenols Section: 13.12

116. Predict the product for the following reaction. OH Na₂Cr₂O₇/H₂SO₄/H₂O Ans: O O . Topic: Synthesis Section: 13.13

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11703

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

CH₃CH₂CHOH CH3 PBr₃ A Mg BH3C H O C H2O D ether Ans: OH Topic: Synthesis Section: 13.13

118. Provide the structure for each product (A-C) in the following reaction sequence.

CH₃CH₂CHOH CH3 PBr₃ A Mg B H3C H O C 2. H₂O ether 1. Ans: OH Br _MgBr A _B _C Topic: Synthesis Section: 13.13

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11904

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

OH PBr3 _A Mg _B _C H2O _D PCC CH2Cl2 O O IV V ether E H H O OH OH I II H O III A) I B) II C) III D) IV E) V Ans: C Topic: Synthesis Section: 13.13

120. Provide the structure for each product (A-D) in the following reaction sequence.

OH PBr3 _A Mg _B _C 2. H₂O PCC CH2Cl2 ether H H O 1. D Ans: OH MgBr Br O A B C _D Topic: Synthesis Section: 13.13

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10512

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

PBr₃ OH Mg D₂O A ether A) CH3CH2CH2CH3 B) CH3CH2CHDCH3 C) CH3CH2CHODCH3 D) CH3CH2CH2CH2OD E) CH3CH2CH2CH2D Ans: B Topic: Synthesis Section: 13.13

2.

OH O Ans: 1. PBr3 2. Mg/ether 3. H O 4. H2O 5. PCC/CH2Cl2 Topic: Synthesis Section: 13.13

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10712

3. Provide a stepwise synthesis for the following.

Ans: O Cl2 1. CH3MgBr Cl OH CH3CH2ONa H2SO4 H3O+ OH PCC CH2Cl2 h 2. H2O heat Topic: Synthesis Section: 13.13

Difficulty Level: Hard 10812

4.

Provide the product for the following reaction sequence:

MgBr H2O MgBr H2O ether K₂Cr₂O₇/H₂SO₄/H₂O ether OH _PCC CH2Cl2 OH O HO O I II III IV _V A) I B) II C) III D) IV E) V Ans: C

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Topic: Synthesis Section: 13.13

Difficulty Level: MediumHard 10912

5.

Predict the product, for the following reaction sequence,

SOCl2 H O CrO3/ H2SO4/H2O Mg/ether 2. H3O+ 1. pyridine 3,4-dimethyl-1-hexanol OH O OH O H O I II III IV V OH A) 6,7-dimethyl-3-nonanolI B) 6,7-dimethyl-3-nonanoneII C) 6,7-dimethyl-3-nonanalIII D) 3,4-dimethyl-7-nonanolIV E) 3,4-dimethyl-7-nonanoneV Ans: B Topic: Synthesis Section: 13.13

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11012

6. Provide a stepwise synthesis for the following.

O Ans: Br2 Cl CH3CH2ONa OH PCC CH2Cl2 h 1. BH₃ THF 2. H2O2/NaOH/H2O O Topic: Synthesis Section: 13.13

Difficulty Level: Hard 11112

7. Provide the reagents necessary to carry out the following conversion.O O Ans: 1. Cl2/h 2. CCONa 3. KMnO4/NaOH/H2O 4. excess PCC/CH2Cl2 5. Topic: Synthesis Section: 13.13

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11212

HO O HO HO Ans: 1. _(CH 3)3SiCl/ (CH3CH2)3N 2. _CH 3MgBr 3. _H 3O+ 4. Topic: Synthesis Section: 13.13

9.

Br OH O Ans: 1. NaOH 2. Na2Cr2O7/H2SO4/H2O 3. Topic: Synthesis Section: 13.13

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11413

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

Ans: Br2 Br CH₃CH₂ONa PCC CH2Cl2 O _OH CH₃ H2SO4 OH 1. BH₃ THF 2. H₂O₂/NaOH/H₂O h 1. CH₃MgBr 2. H₂O _heat H₂/Pd Br2 Br CH3CH2ONa PCC CH2Cl2 O _OH CH3 H2SO4 OH 1. BH3 2. H₂O₂/NaOH/H₂O h 1. CH3MgBr 2. H2O heat H2/Pd Topic: Synthesis Section: 13.13

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131. Provide a stepwise synthesis to carry out the following conversion. OH OH O Ans: OH OH O PBr₃ Br Mg/ether MgBr 1. OH H H O 2. H2O CrO3/H2SO4/H2O Topic: Spectroscopy Section: 13 & 15.6

132. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

I _II _III IV OH C OH N OH HO C O N A) I B) II C) III D) IV E) V Ans: A Topic: Spectroscopy Section: 13 & 15.6

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133. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH O OH O OH I II III IV OH V OH A) I B) II C) III D) IV E) V Ans: E Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard

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134. Which of the following compounds is consistent with the following proton decoupled 13 C NMR spectrum? 0 10 20 30 40 50 60 70 80 PPM OH HO OH I II _III IV OH A) I B) II C) III D) IV E) none of these Ans: B Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard

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135. Which of the following compounds is consistent with the following proton decoupled 13 C NMR spectrum? 0 10 20 30 40 50 60 70 PPM OH HO OH I II _III OH IV A) I B) II C) III D) IV E) none of these Ans: A Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard

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136. A compound with a molecular formula C9H12O has the following 1 HNMR spectrum.

Which of the following structures is consistent with this spectrum?

0 1 2 3 4 5 6 7 PPM exchanges with D2O 2 2 1 2 2 3 O _OH OH OH _OH I II III IV V A) I B) II C) III D) IV E) V Ans: C Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard

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137. A compound with a molecular formula C6H14O displays the following 1 HNMR and 13

CNMR spectra. Propose astructure for this compound.

0 10 20 30 40 50 60 70 80 90 PPM Ans: OH 9 3 1 2