Chemistry: Nomenclature of Alcohols. Chapter Thirteen. Contains 137 Questions and Answers.

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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-d... imethyl-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 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 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 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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 5. What is the IUPAC name for the following compound? 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 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 OH I II III IV A) I B) II C) III D) IV E) None of these D Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 7. What is the IUPAC name for the following compound? 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 E Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 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 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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 10. What is the IUPAC name for the following compound? CH3 C HO H C CCH 2CH3 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 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 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? IV V I II HO HO OH OH III OH A) I B) II C) III D) IV E) V E Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 13. What is the IUPAC name for the following compound? OH 7-ethyl-8-methyl-4-nonanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 14. What is the IUPAC name for the following compound? HO (R)-3-ethyl-2-methyl-3-heptanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 15. What is the IUPAC name for the following compound? OH Br (1R,2S)-2-bromo-1-methylcyclopentanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 16. What is the IUPAC name for the following compound? OH 7-cyclohexyl-2,8-dimethyl-3-decanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 17. Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol? OH Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 18. Provide the structure for 5-chloro-2-propyl-1-heptanol. l OH Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 19. Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol. OH Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 20. What is the IUPAC name for the following compound? OH 4-isobutyl-2-methyl-3-octanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Hard 21. What is the IUPAC name for the following compound? C C C CH3(CH2)4 HO H H (S)-1-octyn-3-ol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 22. What is the IUPAC name for the following compound? HO 4,5,6-tripropyl-4-decanol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 23. What is the IUPAC name for the following compound? HO 3-ethyl-3-cyclohexen-1-ol Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy 24. What is the correct structure for 2-methylphenol? I II III IV V OH OH HO OH OH A) I B) II C) III D) IV E) V Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 25. What is the correct structure for 2-bromo-5-isopropylphenol? I II III IV V OH OH Br OH OH Br Br OH Br Br A) I B) II C) III D) IV E) V B Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 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 Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Medium 27. What is the IUPAC name for the following compound? OH 2-sec-butyl-5-ethylphenol Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Medium 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 D Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard 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 E Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard 3026. What is the IUPAC name for the following compound? OH OH 3,5-dimethyl-2,4-heptanediol Topic: Nomenclature of alcohols Section: 13.5 Difficulty Level: Hard 3127. Provide the structure for (2R, 3S)- 2-bromo-1,3-pentanediol. OH OH Br Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Hard 3228. Explain why cyclohexanol has a pKa of 18 and phenol has a pKa of 10. Use structural drawings to explain your reasoning. 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 3329. Rank the following alcohols in decreasing order of acidity. OH Br OH F OH I I II III II>I>III Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 340. Which one of the following alcohols is most acidic? O OH O OH OH I II III I Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 351. Rank the following alcohols in decreasing order of acidity. Explain your answer. F OH F OH OH I III II F F 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. Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 362. Rank the following alcohols in decreasing order of acidity. O2N OH OH NC OH I II III I>III>II Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 373. Predict the product(s) for the following reaction. OH Na ONa + 1 H2 2 Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 38. Predict the product(s) for the following reaction. Li OH O Li H2 1 2 + Topic: Acidity of alcohols and phenols Section: 13.2 Difficulty Level: Medium 394. Predict the product for the following reaction. OH 1. NaH 2. CH3CH2Br O Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 3540. Provide the reagents necessary to carry out the following conversion. CH3CH2CH2CHCH3 Br CH3CH2CH2CH2CH2OH 1. (CH3)3COK 2. BH3 3. •THF 4. H2O2/NaOH/H2O Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 4136. Predict the product(s) for the following reaction. 1. BH3 THF 2. H2O2/NaOH/H2O OH OH OH CH2OH + enaIntiomer + enIaIntiomer III IV A) I B) II C) III D) IV E) None of these B Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 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 Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 3843. Provide the reagents necessary to carry out the following conversion. (E)-3-methyl-3-hexene 3-methyl-3-hexanol H3O+ OR 1. Hg(OAc)2, H2O 2. NaBH4 Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 3944. Predict the major product for the following reaction. H3O+ OH Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 450. Predict the product for the following reaction. 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 Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Medium 461. Provide the reagents necessary to carry out the following conversion. Br OH NaOH Topic: Preparation of Alcohols Section: 13.3 Difficulty Level: Hard 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 D Topic: Oxidation states Section: 13.4 Difficulty Level: Easy 483. What is the oxidation state of the carbon atoms I and II in the following reactioncompound? O I 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 E Topic: Oxidation states Section: 13.4 Difficulty Level: Easy 494. What is the oxidation state of the carbon atoms I and II in the following reaction? CH3CH O CH3COH O I A) I. +1, II. +2 II B) I. +2, II. +2 C) I. +1, II. +3 D) I. +3, II. +2 E) I. +2, II. +1 Topic: Oxidation states Section: 13.4 Difficulty Level: Medium 450. For the following conversion, identify if the starting material has been oxidized, reduced or neither. Explain your answer. OH O 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 Difficulty Level: Medium 5146. For the following conversion, identify if the starting material has been oxidized, reduced or neither. Cl Cl Oxidized. Topic: Oxidation states Section: 13.4 Difficulty Level: Medium 4752. For the following conversion, identify if the starting material has been oxidized, reduced or neither. Explain your answer. OH O Neither. The oxidation state of the carbon atoms is not changed. Topic: Oxidation states Section: 13.4 Difficulty Level: Hard 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 B Topic: Oxidation states Section: 13.4 Difficulty Level: Hard 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 Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Easy 4955. Predict the product for the following reaction. CH3CCH2CH2CH3 O NaBH4/CH3OH CH3CHCH2CH2CH3 OH Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Medium 560. Predict the product for the following reaction. H O NaBH4/CH3OH OH OH OH O OH OH I II III IV A) I B) II C) III D) IV Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Medium 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 Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 582. Provide the reagents necessary to carry out the following conversion. HC CCH2CH2CH3 CH3CHCH2CH2CH3 OH 1. H3O+/ HgSO4 2. NaBH4/CH3OH OR 1. H2/Ni2B (OR Na, NH3) 2. H3O+ Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 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 Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 5460. Predict the product for the following reaction. COCH3 O O NaBH4 / H2O COCH3 O H HO Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 5561. Predict the product for the following reaction. COCH3 O O 1. LiAlH4 2. H2O excess H2OH H HO Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Hard 5662. Predict the product for the following reaction. HgSO4 H2O / H2SO4 NaBH4/CH3OH OH Topic: Preparation of Alcohols via Reduction Section: 13.4 Difficulty Level: Medium 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 Topic: Preparation of Diols Section: 13.5 Difficulty Level: Easy 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 Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 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 BA Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 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 D Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 671. Provide the structure(s) of the each product (A-D)(s) in the following reaction sequence. C A B Br2 h H3CH2ONa mCPBA NaOH/H2O C D Br O CH3 CH3 OH OH H A B C D + enantiomer + enantiomer Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard 682. Predict the product for the following reaction. 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 Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 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 Topic: Preparation of Diols Section: 13.5 Difficulty Level: Medium 7064. Provide the reagent(s) necessary to carry out the following conversion. OH OH 1. mCPBA 2. H3O+ OR NaOH/H2O Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard 6571. Provide the reagent(s) necessary to carry out the following conversion. OH OH 1. O3 2. (CH3)2S 3. excess NaBH4/CH3OH 4. Topic: Preparation of Diols Section: 13.5 Difficulty Level: Hard 6672. Predict the product(s) for the following reaction. O O 2. H2O 1. excess LiAlH4 O OH OH OH Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Easy 6773. Predict the product for the following reaction sequence. O 2. H2O 1. CH3CH2MgBr HO Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 6874. Predict the product for the following reaction sequence. Br H O Mg/ether 2. H2O 1. OH Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 6975. Provide the reagent(s) necessary to carry out the following conversion. O OH O 1. excess CH3MgBr/ether 2. H2O Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 760. Predict the product for the following reaction. 1. CH3CH2CH2MgBr/ether 2. H2O O OH HO I II OH III IV OH A) I B) II C) III D) IV E) None of these Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 771. Predict the product for the following reaction. Br Mg/ether H H O 1. 2. H2O OH Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 78. Using Grignard reaction, show how you could prepare the following alcohol. OH MgBr 1. 2. H2O H C H O Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 79. Using Grignard reaction, show how you could prepare the following alcohol. OH O MgBr O MgBr OR 1. 2. H2O 2. H2O 1. Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 80. Using Grignard reaction, show how you could prepare the following alcohol. HO O MgBr OR 1. 2. H2O 2. H2O 1. MgBr O 1. MgBr 2. H2O O OR Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 7281. Provide the reagent(s) necessary to carry out the following conversion. HO 1. HBr 2. Mg/ether 3. H H O 4. H2O Topic: Preparation of Alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 7382. Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction. O MgBr 1. 2. H2O Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Medium 7483. Predict the product for the following reaction. OCH3 O 2. H2O 1. CH3CH2CH2MgBr excess OH Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 84. Predict the product for the following reaction. 2. H2O 1. CH3CH2MgBr excess O O OH OH Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 85. Predict the product for the following reaction. 2. H2O 1. CH3CH2MgBr excess O O O OH Topic: Preparation of alcohols via Grignard Reagents Section: 13.6 Difficulty Level: Hard 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 OH Mechanism O O O CH O O 3CH2MgBr O O O O O O CH3CH2MgBr + CH3OMgBr + CH3OMgBr O CH3CH2MgBr H O H HO + OH Topic: Protection of alcohols Section: 13.7 Difficulty Level: Hard 7587. Provide the reagent(s) necessary to carry out the following conversion. HO Br HO OH 1. (CH3)3SiCl / (CH3CH2)3N 2. Mg/ether 3. O 4. H2O 5. TBAF Topic: Protection of alcohols Section: 13.7 Difficulty Level: Hard 88. Provide the reagent(s) necessary to carry out the following conversion. O HO HO OH 1. CH3)3SiCl / (CH3CH2)3N 2. MgBr 3. H2O 4. TBAF Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium 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 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 7790. Predict the product(s) for the following reaction sequence. Br OH H H O Mg/ ether TBAF 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 B Topic: Protection of alcohols Section: 13.7 Difficulty Level: Medium 7891. Provide the reagents necessary to carry out the following conversion. HO HO 1. (CH3)3SiCl / (CH3CH2)3N 2. NaNH2 3. CH3CH2CH2Br 4. TBAF Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy 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  B Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Easy 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 D Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 8194. Predict the product for the following reaction. OH PBr3 Br Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard 8295. Predict the major product for the following reaction and provide a curved arrow mechanism for the formation of the product. OH HBr Br Mechanism OH H Br OH2 + Br H Br Br + H2O Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard 8396. Predict the major product for the following reaction. OH HCl Cl Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 8497. Predict the product for the following reaction. SOCl2/pyridine OH Cl Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 8598. Predict the major product for the following reaction. H H OH CH3 1. TsCl /pyridine 2. NaI H H I C H3 H H OTs CH3 I H H C H3 H H Ts CH3 I II III IV A) I B) II C) III D) IV E) both I and III Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 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 Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 8710 0. 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. Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 8810 1. Explain why the following reaction will not produce an alcohol as product. Cl NaOH OH not produced 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. Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 89102 . Predict the major product for the following reaction. OH 1. TsCl/pyridine 2. CH3CH2ONa Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 9010 3. Predict the major product for the following reaction. OH H2SO4  Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 9110 4. Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane. . 1. H2SO4, heat 2. H2/Pd OR OR 1. TsCl/pyridine 2. CH3CH2ONa 3. H2/Pd 4. Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium 92105 . Provide a stepwise curved arrow mechanism for the following reaction. HO CH2CH3 CH2CH3 H2SO4  CH2CH3 CH2CH3 CH2CH3 HO CH2CH3 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 + H 2SO4 + H2O Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Hard 9310 6. Predict the product and provide a stepwise curved arrow mechanism for the following reaction. H2SO4 heat OH OH 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 Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy 9410 7. 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 Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 9510 8. 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 B Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy 96109 . Predict the product for the following reaction. OH Na2Cr2O7/H2SO4/H2O O Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy 9711 0. Predict the product for the following reaction. OH CH2Cl2 PCC H O Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Easy 9811 1. Provide the reagents necessary to carry out the following conversion. OH H O A) KMnO4/NaOH/H2O B) Na2Cr2O7CrO3/H2SO4/H2O C) PCC/CH2Cl2 D) Br2, CCl4 E) None of these Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 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 B Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 1130 0. Predict the product for the following reaction. OH CH2OH PCC/CH2Cl2 excess OH CH O Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 1140 1. Predict the product for the following reaction. OH PCC CH2Cl2 No reaction. Tertiary alcohols do not undergo oxidation reactions. Topic: Reactions of Alcohols Section: 13.10 Difficulty Level: Medium 11502 . Predict the product for the following reaction. PCC cis-4-methylcyclohexanol CH2Cl2 O . Topic: Oxidation of Phenols Section: 13.12 Difficulty Level: Medium 116. Predict the product for the following reaction. OH Na2Cr2O7/H2SO4/H2O O O . Topic: Synthesis Section: 13.13 Difficulty Level: Medium 1170 3. Provide the structure for the final product (D), in the following reaction sequence. CH3CH2CHOH CH3 PBr3 A Mg HB 3C H O C H2O D ether OH Topic: Synthesis Section: 13.13 Difficulty Level: Medium 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. OH Br MgBr A B C Topic: Synthesis Section: 13.13 Difficulty Level: Hard 1190 4. Provide the structure for the final product (E), in the following reaction sequence. OH PBr3 Topic: Synthesis Section: 13.13 Difficulty Level: Hard 120. Provide the structure for each product (A-D) in the following reaction sequence. OH PBr3 A OH Br MgBr O A B C D Topic: Synthesis Section: 13.13 Difficulty Level: Medium 10512 1. Provide the structure for product (A), in the following reaction sequence. PBr3 OH Mg D2O A ether Topic: Synthesis Section: 13.13 Difficulty Level: Medium 10612 2. Provide the reagents necessary to carry out the following conversion. OH O 1. PBr3 2. Mg/ether 3. H O 4. H2O 5. PCC/CH2Cl2 Topic: Synthesis Section: 13.13 Difficulty Level: Hard 10712 3. Provide a stepwise synthesis for the following. C O l2 1. CH3MgBr Cl OH CH3CH2ONa H2SO4 H3O+ OH PCC h CH2Cl2 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 Topic: Synthesis Section: 13.13 Difficulty Level: MediumHard 10912 5. Predict the product, for the following reaction sequence, SOCl2 H O 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 B Topic: Synthesis Section: 13.13 Difficulty Level: Hard 11012 6. Provide a stepwise synthesis for the following. O 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 1. Cl2/h 2. CCONa 3. KMnO4/NaOH/H2O 4. excess PCC/CH2Cl2 5. Topic: Synthesis Section: 13.13 Difficulty Level: Hard 11212 8. Provide the reagents necessary to carry out the following conversion. HO O HO HO 1. (CH3)3SiCl/ (CH3CH2)3N 2. CH3MgBr 3. H3O+ 4. Topic: Synthesis Section: 13.13 Difficulty Level: Medium 11312 9. Provide the reagents necessary to carry out the following conversion. Br OH O 1. NaOH 2. Na2Cr2O7/H2SO4/H2O 3. Topic: Synthesis Section: 13.13 Difficulty Level: Hard 1141 30. Provide a stepwise synthesis to carry out the following conversion. Topic: Synthesis Section: 13.13 Difficulty Level: Hard 131. Provide a stepwise synthesis to carry out the following conversion. Topic: Spectroscopy Section: 13 & 15.6 Difficulty Level: Medium 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 Topic: Spectroscopy Section: 13 & 15.6 Difficulty Level: Medium 133. Which one of the following compounds is consistent with the following IR spectrum? SDBS: National Institute of Advanced Industrial Science and Technology E Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard 134. Which of the following compounds is consistent with the following proton decoupled 13C NMR spectrum? 80 70 60 50 40 30 20 10 0 D) IV E) none of these B Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard 135. Which of the following compounds is consistent with the following proton decoupled 13C NMR spectrum? 70 60 50 40 30 20 10 0 E) none of these Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard 136. A compound with a molecular formula C9H12O has the following 1HNMR spectrum. Which of the following structures is consistent with this spectrum? 7 6 5 4 3 2 1 0 Topic: Spectroscopy Section: 13, 16.11 & 16.12 Difficulty Level: Hard 137. A compound with a molecular formula C6 H1 4 O displays the following 1HNMR and 13CNMR spectr . Propose astructure for this compound. a90 80 70 60 50 40 30 20 10 0 PPM OH 9 3 2 1 [Show More]

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