Structure and Nomenclature. Chemistry TEST BANK. Chapter Eleven. All Answers highlighted.

Structure and Nomenclature 1. What is the relationship between alcohols I and II?CH3OHCH3HOI IIThey are:A) different conformations of the same compound.B) constitutional isomers.C) enantiomers.D) diastereomers.E) identical.191Topic: Structure and Nomenclature Section: 5.3 and 11.12. What is the relationship between alcohols I and II?I IICH3OHCH3OHThey are:A) different conformations of the same compound.B) constitutional isomers.C) enantiomers.D) diastereomers.E) identical.Topic: Structure and Nomenclature Section: 5.3 and 11.13. What is the relationship between alcohols I and II?I IICH3OHOHCH3They are:A) different conformations of the same compound.B) constitutional isomers.C) enantiomers.D) diastereomers.E) identical.192Topic: Structure and Nomenclature Section: 5.3 and 11.14. What is the relationship between alcohols I and II?HCH3OHHCH3HHOHI II They are:A) different conformations of the same compound.B) constitutional isomers.C) enantiomers.D) diastereomers.E) identical.Topic: Structure and Nomenclature Section: 5.12 and 11.15. What is the relationship between alcohols I and II?HCH3OHHHCH3HOHI II They are:A) different conformations of the same compound.B) constitutional isomers.C) enantiomers.D) diastereomers.E) identical.193Topic: Structure and Nomenclature Section: 5.12 and 11.16. What is the relationship between alcohols I and II?CH3HOI IICH3HOThey are:A) different conformations of the same compound.B) constitutional isomers.C) enantiomers.D) diastereomers.E) identical.Topic: Structure and Nomenclature Section: 5.12 and 11.17. What is the relationship between alcohols I and II?I IICH3OHCH3OHThey are:A) different conformations of the same compound.B) constitutional isomers.C) enantiomers.D) diastereomers.E) identical.194Topic: Nomenclature Section: 11.1A Difficulty Level: Easy8. What is the correct IUPAC name for the following compound?CH3CH3CHOHCHCHCH(CH3)2 CH3A) 4-isopropyl-3,4-dimethyl-2-butanolB) 2,3,4-trimethyl-4-pentanolC) 1,1,2,3-tetramethyl-4-pentanolD) 3,4,5-trimethyl-2-hexanolE) 3,4,5,5-tetramethyl-2-pentanolTopic: Nomenclature Section: 11.1A Difficulty Level: Easy9. A correct IUPAC name for isobutyl alcohol is:A) 2-Methyl-1-propanolB) 2-Methyl-1-butanolC) 1-Methyl-1-propanolD) 1,1-Dimethyl-1-ethanolE) 3-Methyl-1-propanolTopic: Nomenclature Section: 11.1A Difficulty Level: Easy10.The IUPAC name of compoundCH3CH2COHCH2CH3CH2CH3is:A) 1,1,1-TriethylmethanolB) 1,1-Diethyl-1-propanolC) 2-Ethyl-3-pentanolD) 3-Ethyl-3-pentanolE) tert-Heptanol195Topic: Nomenclature Section: 11.1A Difficulty Level: Medium11. What is the correct IUPAC name for the following compound?CH3CH2C=CCH2CH3 CH3CH2CH2OH 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-olD) 3-methyl-4-(2-hydroxyethyl)-3-hexeneE) 3-(2-hydroxyethyl)- 3-methyl-3-hexeneTopic: Nomenclature Section: 11.1A Difficulty Level: Medium12. What is a correct IUPAC name for the following compound?HO OHA) 1,2-butanediolB) isopropanolC) 1-propanolD) 1,2-propanediolE) Ethylene glycol196Topic: Nomenclature Section: 11.1A Difficulty Level: Medium13. What is a correct IUPAC name for the following compound?HO OHA) 1,2-butanediolB) isopropanolC) 1-proanolD) Propylene glycolE) 1,2-ethanediolTopic: Nomenclature Section: 11.1A Difficulty Level: Medium14. The correct IUPAC name for tert-butyl alcohol is:A) 1-ButanolB) 2-Methyl-1-propanolC) 2-Methyl-2-propanolD) 2-ButanolE) 1,1-Dimethyl-1-ethanolTopic: Nomenclature Section: 11.1A Difficulty Level: Medium15. 2,2-Dimethyl-1-propanol has the common name:A) Isoamyl alcoholB) Isopentyl alcoholC) tert-Pentyl alcoholD) Neopentyl alcoholE) 2-Methylisobutyl alcohol197Topic: Nomenclature Section: 11.1A Difficulty Level: Medium16. Which of these, though often used, is an incorrect common name for CH3CHOHCH3?A) Isopropyl alcoholB) sec-Propyl alcoholC) 2-PropanolD) IsopropanolE) More than one of these.Topic: Nomenclature Section: 11.1A Difficulty Level: Medium17. Which of these, though often used, is an incorrect common name for (CH3)3COH?A) tert-Butyl alcoholB) tert-ButanolC) 2-Methyl-2-propanolD) More than one is incorrect.E) Each is a correct name.Topic: Isomerism, Stereoisomers Section: 11.1ADifficulty Level: Medium18. Which of the following can be described as “optically active, primary alcohol”?A) CH3CH2CH2CH2CH2OHB) (CH3)2CHCH2CH2OHC) CH3CH2CH(CH3)CH2OHD) (CH3)2CHCHOHCH3E) Two of the above198Topic: Nomenclature Section: 11.1A 19.The correct IUPAC substitutive name forOHis:A) 4-Penten-2-methyl-2-olB) 4-Methyl-1-penten-2-olC) 2-Methyl-4-penten-2-olD) 4-Methyl-1-penten-4-olE) 4-Hydroxy-4-methyl-1-penteneTopic: NomenclatureSection: 11.1A 20. OHOHis properly named: A) cis-1,2-Cyclopentanediol B) meso-1,2-Cyclopentanediol C) (1R,2R)-1,2-Cyclopentanediol D) (1R,2S)-1,2-CyclopentanediolE) (1S,2S)-1,2-Cyclopentanediol199Topic: Nomenclature Section: 11.1A 21. OHOHis properly named: A) 1,2-Cyclopentanediol B) 1,5-Cyclopentanediol C) (1R,2R)-1,2-Cyclopentanediol D) (1R,2S)-1,2-CyclopentanediolE) (1S,2S)-1,2-CyclopentanediolTopic: NomenclatureSection: 11.1A 22. OHOHis properly named: A) cis-1,2-Cyclohexanediol B) meso-1,2-Cyclohexanediol C) (1R,2R)-1,2-Cyclohexanediol D) (1R,2S)-1,2-CyclohexanediolE) (1S,2S)-1,2-Cyclohexanediol200Topic: Nomenclature Section: 11.1A 23. OHOHis properly named: A) 1,2-Cyclohexanediol B) 1,6-Cyclohexanediol C) (1R,2R)-1,2-Cyclohexanediol D) (1R,2S)-1,2-CyclohexanediolE) (1S,2S)-1,2-CyclohexanediolTopic: NomenclatureSection: 11.1A 24. OHOHis properly named: A) 1,3-Cyclopentanediol B) 1,4-Cyclopentanediol C) (1R,3R)-1,3-Cyclopentanediol D) (1R,3S)-1,3-CyclopentanediolE) (1S,3S)-1,3-Cyclopentanediol201Topic: Nomenclature Section: 11.1A 25. HOOHis properly named: A) 1,4-Cycloheptanediol B) 1,5-Cycloheptanediol C) (1R,4R)-1,4-Cycloheptanediol D) (1R,4S)-1,4-CycloheptanediolE) (1S,4S)-1,4-CycloheptanediolTopic: Nomenclature Section: 11.1A 26. A correct name for the following Fischer projection formula is:OHHH3C C C CH3A) (R)-3-Pentyn-2-olB) (S)-3-Pentyn-2-olC) (R)-2-Pentyn-4-olD) (S)-2-Pentyn-4-olE) (S)-2-Hydroxy-3-pentyne202Topic: Stereoisomerism Section: 11.1B Difficulty Level: Easy27. What is the relationship between alcohols I and II?CH3HOI IICH3OHThey are:A) different conformations of the same compound.B) constitutional isomers.C) enantiomers.D) diastereomers.E) identical.203Topic: Nomenclature Section: 11.1B Difficulty Level: Medium28. Select the structure of benzyl methyl ether.CH3 O CH3CH3OCH3 O CH2CHCH3O CHCH3CH3 CH2 O CH2 CH3I I IIIIIVVA) IB) IIC) IIID) IVE) VTopic: Nomenclature Section: 11.1B Difficulty Level: Medium29. Which is a correct IUPAC name for CH3CH2OCH2CH2CH2OCH2CH3?A) 1,4-DioxaneB) Ethylene glycol diethyl etherC) 1,3-DiethoxypropaneD) 1,2-DiethoxyethaneE) 1,2-Diethoxymethane204Topic: Isomerism, Stereoisomers Section: 11.1BDifficulty Level: Medium30. What is the total number of pentyl alcohols, including stereoisomers?A) 7B) 8C) 9D) 10E) 11Topic: Isomerism, Stereoisomers Section: 11.1BDifficulty Level: Medium31. The number of primary alcohols corresponding to the formula C5H12O, countingstereoisomers separately, is:A) 1B) 2C) 3D) 4E) 5Topic: Isomerism, Stereoisomers Section: 11.1BDifficulty Level: Medium32. The number of tertiary alcohols corresponding to the formula C5H12O, countingstereoisomers separately, is:A) 1B) 2C) 3D) 4E) 5205Topic: Isomerism, Stereoisomers Section: 11.1BDifficulty Level: Medium33. The number of secondary alcohols corresponding to the formula C5H12O, countingstereoisomers separately, is:A) 1B) 2C) 3D) 4E) 5Topic: Isomerism, Stereoisomers Section: 11.1BDifficulty Level: Medium34. The total number of ethers corresponding to the formula C5H12O, counting stereoisomersseparately, is:A) 4B) 5C) 6D) 7E) 8Topic: Isomerism, Stereoisomers Section: 11.1BDifficulty Level: Medium35. The number of optically active pentyl alcohols (C5H11OH), i.e., the total number ofindividual enantiomers, is:A) 0B) 2C) 3D) 4E) 6206Topic: Nomenclature Section: 11.1B 36. What is the most accurate name for the molecule represented by the following Fischerprojection formula?HOCH3CH3H3CH2CA) sec-Butyl methyl etherB) Isobutyl methyl etherC) tert-Butyl methyl etherD) (R)-2-MethoxybutaneE) (S)-2-MethoxybutaneTopic: Physical Properties, Comparison Section: 11.2Difficulty Level: Easy37. Which of the compounds listed below would you expect to have the highest boilingpoint? (They all have approximately the same molecular weight.)A) CH3CH2CH2CH2CH3B) CH3CH2CH2CH2OHC) CH3CH2CH2OCH3D) CH3CH2CH2ClE) CH3CH2OCH2CH3Topic: Physical Properties, Comparison Section: 11.2Difficulty Level: Easy38. Which compound would have the highest boiling point?A) CH3CH2CH2CH3B) CH3CH2OCH3C) CH3CH2CH2OHD) (CH3)2CHOHE) HOCH2CH2OH207Topic: Physical Properties, Comparison Section: 11.2Difficulty Level: Easy39. Which compound would have the lowest boiling point?A) CH3CH2CH2CH3B) CH3CH2OCH2CH3C) CH3CH2CH2OHD) (CH3)2CHOHE) HOCH2CH2OHTopic: Physical Properties, Comparison Section: 11.2Difficulty Level: Easy40. Which compound would have the highest boiling point?A) CH3CH2CH2CH3B) CH2(OH)CH(OH)CH2OHC) CH3CH2CH2OHD) (CH3)2CHOHE) HOCH2CH2OHTopic: Physical Properties, Comparison Section: 11.2Difficulty Level: Easy41. Which compound would have the lowest solubility in water?A) Diethyl etherB) Methyl propyl etherC) 1-ButanolD) 2-ButanolE) Pentane208Topic: Physical Properties, Comparison Section: 11.2Difficulty Level: Easy42. Which compound would have the greatest solubility in water?A) Diethyl etherB) Methyl propyl etherC) 1-ButanolD) 1,2-ButanediolE) PentaneTopic: Physical Properties, Comparison Section: 11.2Difficulty Level: Easy43. Which compound would have the lowest boiling point?I II III IV VOOHOH CH2OHOHA) I B) II C) III D) IV E) V209Topic: Physical Properties, Comparison Section: 11.2Difficulty Level: Easy44. Which compound would have the highest boiling point?I II IIIIV VOOOHOHOOHO O O OA) IB) IIC) IIID) IVE) VTopic: Ether Reactivity Section: 11.2 Difficulty Level: Easy45. Which of the following statements is NOT true of ethers?A) Ethers are generally unreactive molecules toward reagents other than strong acids.B) Ethers generally have lower boiling points than alcohols of a corresponding molecularweight.C) Ethers generally have much lower water solubilities than alcohols with a correspondingmolecular weight.D) Ethers can generally be cleaved by heating them with strong acids.E) Ethers form peroxides when allowed to stand in the presence of oxygen.210Topic: General Section: 11.3A Difficulty Level: Easy46. The major industrial process in use today for the production of methanol is the:A) hydration of ethyne.B) distillation of wood.C) hydrogenation of carbon dioxide.D) reduction of methanal.E) catalytic reduction of carbon monoxide.Topic: General Section: 11.3B Difficulty Level: Easy47. Today, most industrial ethanol is made in the U.S. by the:A) fermentation of grain.B) hydrolysis of ethyl bromide.C) hydration of ethylene.D) reduction of acetaldehyde.E) hydration of acetylene.Topic: Ether Reaction Rates Section: 11.3DDifficulty Level: Easy48. Which of these ethers is most resistant to peroxide formation on exposure toatmospheric oxygen?A) CH3OCH2CH3B) CH3CH2OCH2CH3C) (CH3)2CHOCH(CH3)2D) (CH3)2CHOCH2CH3E) CH3OC(CH3)3211Topic: Alcohol Synthesis Section: 11.4Difficulty Level: Easy49. Which product(s) would you expect to obtain from the following sequence of reactions?CH3CH3OHCH3OHCH3 H3C CH2OHOOH+ enantiomer+ enantiomer+ enantiomerI II III IV V1. BH3-THF2. H2O2, NaOH?A) I B) II C) III D) IV E) V212Topic: Alcohol Synthesis Section: 11.4Difficulty Level: Easy50. Select the structure of the major product formed from the following reaction.CH3CH3OHCH3OHCH2OH HO CH3 CH3OHI II III IV V1. Hg(OOCCH3)2THF, H2O2. NaBH4, NaOH?A) IB) IIC) IIID) IVE) VTopic: Alcohol Synthesis Section: 11.4Difficulty Level: Easy51. Anti-Markovnikov hydration of the carbon-carbon double bond occurs when an alkenereacts with:A) BH3:THF; then H2O2/OHB) BH3:THF; then CH3COOHC) Hg(OAc)2, THF, H2O; then NaBH4, OHD) Hg(OAc)2, THF, CH3OH; then NaBH4, OHE) Hg(OAc)2, THF, H2O; then BH3:THF213Topic: Reaction Mechanisms Section: 11.4Difficulty Level: Easy52. Which statement is true concerning the formation of alcohols by the hydroborationoxidation sequence?A) Overall, the process results in syn addition and anti-Markovnikov orientation.B) Overall, the process results in anti addition and anti-Markovnikov orientation.C) Overall, the process results in syn addition and Markovnikov orientation.D) Overall, the process results in anti addition and Markovnikov orientation.E) The stereochemistry and orientation are unpredictable.Topic: Alcohol Synthesis Section: 11.4Difficulty Level: Medium53. Which would be the best way to carry out the following synthesis?CH3CH2CHCH3BrCH3CH2CH2CH2OH?A) (1) HA, heat; (2) H3O+, H2O, heatB) (1) (CH3)3COK / (CH3)3COH; (2) BH3:THF, then H2O2, OHC) (1) (CH3)3COK / (CH3)3COH; (2) H3O+, then H2O, heatD) (1) KOH, C2H5OH; (2) BH3:THF, then H2O2, OHE) (1) KOH, C2H5OH; (2) HA, heat; (3) H3O+, H2O, heat214Topic: Alcohol Synthesis, Mechanisms Section: 11.4Difficulty Level: Medium54. Select the potential energy diagram that best represents the following reaction:H+H2OOHA) I B) II C) III D) IV E) V215Topic: Alcohol Synthesis Section: 11.4Difficulty Level: Medium55. Which reaction can accomplish the following transformation in good yield:?OHA) H+/H2OB) oxymercuration/demercuationC) hydroboration/oxidationD) Reaction with NaOHE) None of the aboveTopic: Alcohol Synthesis, Isotope Labeling Section: 11.4Difficulty Level: Medium56. The hydroboration-oxidation procedure can be successfully employed for synthesis of deuterated derivatives, by using BD3 instead of BH3. What product would you expect from the following reaction?CH3CH3HO DH CH3H DH CH3BD2 DH CH3D OHH CH3H BD2D1. (BD3)22. H2O2/NaOH?+ enantiomer I+ enantiomer II+ enantiomer III+ enantiomer IV+ enantiomer VA) I B) II C) III D) IV E) V216Topic: Alcohol Synthesis, Isotope Labeling Section: 11.4Difficulty Level: Medium57. The oxymercuration-demercuration procedure can be successfully employed for synthesis of deuterated derivatives, by using NaBD4 instead of NaBH4 in the second step. What product would you expect from the following reaction?1. Hg(OAc)2/H2O2. NaBD4, NaOH?OHOH DDOHOH D OHI II III IV VA) IB) IIC) IIID) IVE) VTopic: Alcohol Synthesis Section: 11.4Difficulty Level: Medium58. Which of the following would be a reasonable synthesis of 2-butanol?A)1-ButeneRCOOHB) 1-Butene2. H2O2, NaOH1. BH3-THFC) 1-Butene2. NaBH4, NaOH1. Hg(OAc)2, THF, H2OD) 1-Butene1. Ha(OAc)2/CH3OH2. NaBH4, NaOHE) None of these217218Topic: Alcohol Synthesis Section: 11.4Difficulty Level: Medium59. Which of the following would be a reasonable synthesis of CH3CH2CH2CH2OH?A)1-ButeneH3O+, heatB) 1-Butene2. H2O2, NaOH 1. BH3-THFC) 1-Butene2. NaBH4, NaOH1. Hg(OAc)2, THF, H2OD) 1-Butene1. Ha(OAc)2/CH3OH2. NaBH4, NaOHE) None of theseTopic: Alcohol Synthesis Section: 11.4Difficulty Level: Medium60. Which would be the major product of the reaction shown?CH2CH3HOHCH2CH3HOHCH2CH3HHHHCH2CH2OHHHHCH2CH3OHCH2CH3H2. NaBH4, NaOH1. Hg(OAc)2, THF, H2O?OI II III IV VA) IB) IIC) IIID) IVE) V219Topic: Alcohol SynthesisSection: 11.4Difficulty Level: Medium61. What is the major product of the reaction: i) BH3, THF ii) H2O2,NaOHCH3CH3OH OHCH3I II III IVCH3OH?+ enantiomer+ enantiomerA) IB) IIC) III ****D) IVE) Both III and IVTopic: Alcohol Synthesis Section: 11.4Difficulty Level: Medium62. Oxymercuration-demercuration of 3-methylcyclopentene produces this/these product(s):I II III IVHO CH3 CH2OH CH3 CH3OHOHA) IB) IIC) IIID) IVE) Both III and IV220Topic: Alcohol Synthesis Section: 11.463. What is the major product of the reaction when (R)-3-methylcyclohexene is subjected tothe hydroboration-oxidation sequence?A) (1R,2R)-2-methylcyclohexanol + (1S,2R)-2-methylcyclohexanolB) (1S,2R)-2-methylcyclohexanol + (1S,2S)-2-methylcyclohexanolC) (1R,3R)-3-methylcyclohexanol + (1S,3R)-3-methylcyclohexanolD) (1S,3R)-3-methylcyclohexanol (1S,3S)-3-methylcyclohexanolE) Two of the aboveTopic: Alcohol Synthesis Section: 11.464. Which would be the best method for converting 3,3-dimethyl-1-pentene into 3,3-dimethyl-2-pentanol?A) H3O+, heatB) BH3:THF; then H2O2, OHC) concd. H2SO4; then H2O, heatD) Hg(OAc)2/THF-H2O; then NaBH4,OHE) HBr; then NaOH/H2O221Topic: Alcohol Synthesis, Mechanisms Section: 11.465. Assuming an overall exothermic process, select the potential energy diagram that bestrepresents the following reaction:H+H2OHOA) I B) II C) III D) IV E) V222Topic: Alcohol Synthesis Section: 11.466. Select the structure of the major product formed from the following reaction.H3O+?OHOHOHOHOHIII IIIIV VA) I B) II C) III D) IV E) V223Topic: Alcohol Synthesis Section: 11.467. Select the structure of the major product formed from the following reaction.H3O+OHOHOHOHOHIII IIIIV IV?A) I B) II C) III D) IV E) V224Topic: Reaction Mechanisms Section: 8.6 and 11.4 Difficulty Level: Medium68. What is the electrophilic species involved in the initial step of the reaction below?OHHgOAc Hg(OAc)2THF, H2OA) +OHB) +HgOAcC) H3O+D) THFE) the THF/H2O complexTopic: Reaction Mechanisms Section: 8.6 and 11.4 Difficulty Level: Medium69. What is the nucleophilic species involved in the initial step of the reaction below?OHHgOAc Hg(OAc)2THF, H2OA) -OHB) Hg(OAc)2C) H2OD) cyclopenteneE) the THF/H2O complexTopic: Alcohol Reaction Rates Section: 11.8Difficulty Level: Easy70. Which of the alcohols listed below would you expect to react most rapidly with HBr?A) CH3CH2CH2CH2CH2CH2OHB) (CH3CH2)2CH2CH2OHC) (CH3CH2)2CHOHCH3D) CH3CH2CH2CH2CH2OHE) (CH3CH2)2C(CH3)OH225Topic: Alcohol Reaction Rates Section: 11.8Difficulty Level: Medium71. Which alcohol would undergo acid-catalyzed dehydration most rapidly?A) 3,3-dimethyl-1-butanolB) 2,2-dimethyl-1-butanolC) 3,3-dimethyl-2-butanolD) 2-methyl-2-butanolE) All would undergo dehydration equally rapidly.Topic: Alcohol Reactions Section: 11.8A Difficulty Level: Easy72. Which of the following could not be used to synthesize 2-bromopentane efficiently?A) 1-Pentene + HBr B) 2-Pentene + HBr C) 2-Pentanol + HBr D) 2-Pentanol + PBr3 E) All of the above would afford good yields of 2-bromopentane.Topic: Alcohol Reaction Rates Section: 11.8ADifficulty Level: Easy73. Which of these alkyl halide syntheses is predicted to occur at the greatest rate?A) CH3CH2CH2CH2OH + HI →B) (CH3)2CHCH2OH + HBr →C) CH3CHOHCH2CH3 + HCl →D) CH3CHOHCH2CH3 + HBr →E) (CH3)3COH + HI →226Topic: Reaction Mechanisms Section: 11.8ADifficulty Level: Easy74. The following reaction,CH3CH2CH2CH2OH CH3CH2CH2CH2Br + H2OHBrheatis probably:A) an SN1-type reaction involving the protonated alcohol as the substrate.B) an SN2-type reaction involving the protonated alcohol as the substrate.C) an E1-type reaction involving the protonated alcohol as the substrate.D) an E2-type reaction involving the protonated alcohol as the substrate.E) an epoxidation reaction.Topic: Reaction Mechanisms Section: 11.8ADifficulty Level: Medium75. The reaction between 1-pentanol and HBr to yield 1-bromopentanol is probably:A) an SN1-type reaction involving the protonated alcohol as the substrate.B) an SN2-type reaction involving the protonated alcohol as the substrate.C) an E1-type reaction involving the protonated alcohol as the substrate.D) an E2-type reaction involving the protonated alcohol as the substrate.E) an epoxidation reaction.Topic: Reaction Mechanisms Section: 11.8ADifficulty Level: Medium76. The reaction between 2-methyl-2-pentanol and HBr to yield 2-bromo-2-methylpentaneis probably:A) an SN1-type reaction involving the protonated alcohol as the substrate.B) an SN2-type reaction involving the protonated alcohol as the substrate.C) an E1-type reaction involving the protonated alcohol as the substrate.D) an E2-type reaction involving the protonated alcohol as the substrate.E) an epoxidation reaction.227Topic: Reaction Mechanisms Section: 11.8ADifficulty Level: Medium77. The reaction between 2-methyl-2-pentanol and HBr to yield 2-methyl-2-pentene isprobably:A) an SN1-type reaction involving the protonated alcohol as the substrate.B) an SN2-type reaction involving the protonated alcohol as the substrate.C) an E1-type reaction involving the protonated alcohol as the substrate.D) an E2-type reaction involving the protonated alcohol as the substrate.E) an epoxidation reaction.Topic: Reaction Mechanisms Section: 11.8ADifficulty Level: Medium78. The reaction between 4-methyl-1-pentanol and HBr to yield 4-methyl-1-pentene isprobably:A) an SN1-type reaction involving the protonated alcohol as the substrate.B) an SN2-type reaction involving the protonated alcohol as the substrate.C) an E1-type reaction involving the protonated alcohol as the substrate.D) an E2-type reaction involving the protonated alcohol as the substrate.E) an epoxidation reaction.228Topic: Alcohol Reactions, MechanismsSection: 11.8ADifficulty Level: Medium79. Assuming an overall exothermic process, select the potential energy diagram that bestrepresents the following reaction:OHH+heat (-H2O)A) I B) II C) III D) IV E) V229Topic: Alcohol Reactions Section: 11.8A Difficulty Level: Medium80. Which of the following could be used to synthesize 2-bromobutane?A) CH3CH2CHCH2 + Br2 (aq) →B) CH3CH2CCH3 + HBr →C) CH3CH2C≡CH + HBr →D) CH3CH2C≡CH + Br2 →E) More than one of the aboveTopic: Alcohol Reactions Section: 11.8A Difficulty Level: Medium81. Which of the following could be used to synthesize 2-iodobutane?A) CH3CH2CHCH2 + I2 (aq) →B) CH3CH2CCH3 + HI →C) CH3CH2C≡CH + HI →D) CH3CH2C≡CH + I2 →E) None of the aboveTopic: Alcohol Reactions Section: 11.8A Difficulty Level: Medium82. Which of the following could be used to synthesize 2-chlorobutane?A) CH3CH2CHCH2 + Cl2 (aq) →B) CH3CH2CCH3 + HCl →C) CH3CH2C≡CH + HCl →D) CH3CH2C≡CH + Cl2 →E) None of the above230Topic: Alcohol Reaction Rates Section: 11.9Difficulty Level: Easy83. Which of the alcohols listed below would you expect to react most rapidly with PBr3?A) CH3CH2CH2CH2CH2CH2OHB) (CH3CH2)2CH(OH)CH2CH3C) (CH3CH2)2CHOHCH3D) (CH3CH2)3COHE) (CH3CH2)2C(CH3)OHTopic: Alcohol Reactions Section: 11.9Difficulty Level: Medium84. Which of the following could be used to synthesize 1-bromobutane efficiently?A) CH3CH2CH=CH2 + HBr →B) CH3CH2CH2CH2OH + PBr3 →C) CH3CH2CH2(OH)CH3 + HBr →D) CH3CH2CH2CH2OH + Br2 →E) None of theseTopic: Alcohol Reactions Section: 11.9Difficulty Level: Medium85. 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 →231Topic: Alcohol ReactionsSection: 11.9Difficulty Level: Medium86.The conversion ofCH CH CH3OHH3CCH3to CH CH CH3BrH3CCH3is bestachieved through use of which of these reagents in a low temperature reaction?A) Concd. HBrB) Br2C) NaBr, H2SO4D) PBr3E) HBr, peroxideTopic: Alcohol Reactions Section: 11.9Difficulty Level: Medium87. The conversion of 3-methyl-1-octanol to 1-chloro-3-methyloctane is best achievedthrough use of which of these reagents?A) Concd. HClB) SO2Cl2C) NaCl, H2SO4D) PCl3E) POCl3Topic: Reaction Mechanisms Section: 11.9Difficulty Level: Medium88. The reaction between 4-methyl-1-pentanol and PBr3 to yield 1-bromo-4-methylpentaneis probably:A) an SN1-type reaction involving the protonated alkyl dibomophosphite of the alcohol asthe substrate.B) an SN2-type reaction involving the protonated alkyl dibomophosphite of the alcohol asthe substrate.C) an E1-type reaction involving the protonated alkyl dibomophosphite of the alcohol asthe substrate.D) an E2-type reaction involving the protonated alkyl dibomophosphite of the alcohol asthe substrate.E) an epoxidation reaction.232Topic: Alcohol Reactions Section: 11.8 and 11.9 Difficulty Level: Medium89. Which of the following reactions would serve as a synthesis of butyl bromide?A) CH3CH2CH2CH2OH + HBr refluxB) CH3CH2CH2CH2OH + PBr3 →C) CH3CH2CH2CH2OH + NaBr refluxD) CH3CH2CH2CH2OH + Br2 →E) Answers A) and B) onlyTopic: Alcohol Reactions Section: 11.8 and 11.9 Difficulty Level: Medium90. Which reagent(s) would transform propyl alcohol into propyl bromide?A) Concd. HBr and heatB) PBr3C) NaBr/H2O and heatD) More than one of theseE) All of these233Topic: General Section: 11.10 Difficulty Level: Easy91. Which compound is a tosylate?CH3 S OO OCH3 Br S OO OCH2 CH3 S OOCH3CH3 S CH3OCH3 S O OCH3CH3OI II IIIIV VA) IB) IIC) IIID) IVE) V234Topic: Alcohol Reactions Section: 11.10 92. What would be the major product of the following reaction sequence?H HOHCH3H HI C H3I HH C H3H II C H3H HOSO2ICH3CH3SO2Cl basemesylateNaI ethanol?I II III IVA) IB) IIC) IIID) IVE) An equimolar mixture of I and II235Topic: Alcohol Reactions Section: 11.10 93. What would be the major product of the following reaction sequence?OHHCH3HCH3SO2Cl basemesylateNaIethanol?H HCH3II HCH3HH ICH3IH HCH3SO2II II III IVA) IB) IIC) IIID) IVE) An equimolar mixture of I and II236Topic: Alcohol Reactions Section: 11.10 94. What would be the major product of the following reaction sequence?OHHCH3HpCH3C6H4SO2Cl basetosylateNaIethanol?H HCH3II HCH3HH ICH3IH HCH3SO2C6H4CH3I II III IVA) IB) IIC) IIID) IVE) An equimolar mixture of I and II237Topic: Alcohol Reactions Section: 11.10 95. What would be the major product of the following reaction sequence?OHHCH3HpCH3C6H4SO2Cl basetosylateNaBr ethanol?H HCH3BrBrHCH3HH B rCH3BrH HCH3SO2C6H4CH3I II III IVA) IB) IIC) IIID) IVE) An equimolar mixture of II and III238Topic: Alcohol Reactions Section: 11.10 96. What would be the major product of the following reaction sequence?OHHCH3HpCH3C6H4SO2Cl basetosylateNaOH?H HCH3OHOHHCH3HH O HCH3OHH HCH3SO2C6H4CH3I II III IVH2OA) IB) IIC) IIID) IVE) An equimolar mixture of I and IITopic: Alcohol Reactions Section: 11.10 97. cis-3-Methylcyclopentanol is treated with CH3SO2Cl in the presence of a base. Theproduct of the reaction then is allowed to react with KI in methanol. What is the finalproduct?A) trans-1-Iodo-3-methylcyclopentaneB) cis-1-Iodo-3-methylcyclopentaneC) 1-MethylcyclopenteneD) 2-MethylcyclopenteneE) 3-Methylcyclopentene239Topic: Alcohol Reactions Section: 11.10 98. The major product of the following reaction would be:CH3SO2Cl baseProduct ?I II IIIC2H5H OHCH3CH3CO2-C2H5H3CCO2 HCH3C2H5H O2CCH3CH3C2H5H3CCO2 OSO2CH3CH3A) IB) IIC) IIID) Equal amounts of I and IIE) None of theseTopic: Alcohol Reactions Section: 11.10 99. trans-3-Methylcyclopentanol is treated with CH3SO2Cl in the presence of base. Theproduct of this reaction is then heated with KI in methanol. What is the final product?A) trans-1-Iodo-3-methylcyclopentaneB) cis-1-Iodo-3-methylcyclopentaneC) 1-MethylcyclopenteneD) 2-MethylcyclopenteneE) 3-Methylcyclopentene240Topic: Alcohol Reactions/Stereochemistry Section: 11.10100. Methanesulfonic acid, OH,OCH3 is treated, in turn, with PCl5 and (R)-2-butanol.S OWhich of the following Fischer formulas is a stereochemically correct representation of the final product?CH3CH2CH3MsO HH C H2CH3MsO CH3H C H2CH3S CH3O OH3CCH3CH2CH3S HO OH3CCH3CH2CH3S ClO OH3CI II IIIIV VA) I B) II C) III D) IV E) V241Topic: Reaction Mechanisms Section: 11.11Difficulty Level: Medium101. The following reaction, 2 CH3CH2CH2CH2OH (CH3CH2CH2CH2)2O + H2OH2SO4heatis probably:A) an SN1-type reaction involving the protonated alcohol as the substrate.B) an SN2-type reaction involving the protonated alcohol as the substrate.C) an E1-type reaction involving the protonated alcohol as the substrate.D) an E2-type reaction involving the protonated alcohol as the substrate.E) an epoxidation reaction.Topic: Ether Synthesis Section: 11.11B Difficulty Level: Medium102. Which is the best way to prepare 3-methoxypentane via the Williamson method?A) CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140CB) CH3OH + (CH3)2CHCH2CH2OH + H2SO4, 140CC) CH3ONa + (CH3CH2)2CHBrD) CH3I + (CH3CH2)2CHONaE) CH3I + (CH3)2CHCH2CH2ONaTopic: Ether Synthesis Section: 11.11B Difficulty Level: Medium103. Which method would provide the best synthesis of ethyl isopropyl ether?A) (CH3)2CHONa + CH3CH2Br →B) CH3CH2ONa + (CH3)2CHBr →C)CH3CH2OH + (CH3)2CHOHH2SO4, 140 oCD) CH3CH2OH + (CH3)2CHOHH2SO4, 180 oCE) CH3CH2ONa + (CH3)2CHOH →242Topic: Ether Synthesis Section: 11.11B Difficulty Level: Medium104. Which is the best method for the synthesis of tert-butyl methyl ether?A) CH3ONa + (CH3)3CBr →B) (CH3)3CONa + CH3I →C) CH3OH + (CH3)3COH + H2SO4 at 140° C →D) (CH3)3CONa + CH3OCH3 →E) CH3ONa + (CH3)3COH →Topic: Ether Synthesis Section: 11.11B 105. Which is the best method to prepare 2-ethoxy-5-methylhexane?A) C2H5ONa + (CH3)2CHCH2CH2BrB) C2H5ONa + (CH3)2CHCH2CH2CH2CH2BrC) C2H5ONa + (CH3)2CHCH2CH2CHBrCH3D) C2H5Br + (CH3)2CHCH2CH2CH(CH3)ONaE) C2H5OH + (CH3)2CHCH2CH2CHOHCH3 + H2SO4, 140CTopic: Ether Synthesis Section: 11.11C 106. When 3-methyl-2-pentene is treated with mercuric acetate, Hg(O2CCH3)2, in a THFethanol mixture and the resulting product reacted with NaBH4 in basic solution, theprincipal product formed is which of these?A) 3-methyl-3-pentanolB) 3-ethoxy-3-methylpentaneC) 3-methyl-2-pentanolD) 2-ethoxy-3-methylpentaneE) 1-ethoxy-3-methylpentane243Topic: Ether Synthesis Section: 11.11C 107. When 3-methyl-2-pentene is treated with mercuric acetate, Hg(O2CCH3)2, in a THF-tbutyl alcohol mixture and the resulting product reacted with NaBH4 in basic solution,the principal product formed is which of these?A) 3-methyl-3-pentanolB) 3-t-butoxy-3-methylpentaneC) 3-methyl-2-pentanolD) 2- t-butoxy -3-methylpentaneE) 1- t-butoxy -3-methylpentaneTopic: Alcohol Reactions Section: 11.11E Difficulty Level: Medium108. What is the product of the reaction of propyl alcohol with (CH3)3SiCl in the presence ofa tertiary amine?A) CH3CH2CH2Si(CH3)3B) (CH3)2CHSi(CH3)3C) CH3CH2CH2OSi(CH3)3D) (CH3)2CHOSi(CH3)3E) (CH3CH2CH2)3SiOH244Topic: Ether Reaction Rates Section: 11.12Difficulty Level: Easy109. Which of these ethers is least likely to undergo significant cleavage by hot aqueousH2SO4 ?I CH3OCH3 II CH3OCH(CH3)2 III(CH3)2CHOCH(CH3)2IV V(CH3)3COC(CH3)3 OA) IB) IIC) IIID) IVE) VTopic: Chemical Tests Section: 11.12 Difficulty Level: Medium110. Which of the reagents listed below would serve as the basis for a simple chemical test todistinguish betweenOand ?A) AgNO3 in alcohol B) NaOH in H2O C) Br2 in CCl4D) Cold concd. H2SO4E) KMnO4 in H2O245Topic: Chemical Tests Section: 11.12 Difficulty Level: Medium111. Which of the reagents listed below would serve as the basis for a simple chemical test todistinguish betweenOandBr?A) AgNO3 in C2H5OHB) Dilute HClC) Br2 in CCl4D) NaOH in H2OE) KMnO4 in H2OTopic: Ether Reactions Section: 11.12A Difficulty Level: Medium112. The product(s) of the following reactionOexcess HBr heatis/are:O OH and BrOH and BrBr BrOBrI IIIIIIVA) IB) IIC) IIID) IVE) None of these246Topic: Ether Reactions Section: 11.12A Difficulty Level: Medium113. The product(s) of the following reactionOexcess HI heatis/are:O OH and IOH and II IOII IIIIIIVA) IB) IIC) IIID) IVE) None of these247Topic: Ether Reactions Section: 11.12A Difficulty Level: Medium114. The product(s) of the following reactionO1 equiv. HIheatis/are:O OH and IOHIOII IIIIIIVA) IB) IIC) IIID) IVE) None of these248Topic: Ether Reactions Section: 11.12A Difficulty Level: Medium115. The product(s) of the following reactionO1 equiv. HIheatis/are:O OHIOIIIIIIIIVOHIA) IB) IIC) IIID) IVE) None of these249Topic: Ether Reactions Section: 11.12A Difficulty Level: Medium116. The product(s) of the following reactionO1 equiv. HIheatis/are:O OHIOIIIIIIIIVOHIA) IB) IIC) IIID) IVE) None of these250Topic: Ether Reactions, Mechanisms Section: 11.12ADifficulty Level: Medium117. Select the potential energy diagram that best represents the following reaction:OCH3HII+ CH3OHA) I B) II C) III D) IV E) V251Topic: Ether Reactions, Mechanisms Section: 11.12ADifficulty Level: Medium118. Assuming an overall exothermic process, select the potential energy diagram that bestrepresents the following reaction:OHIOH + CH3IA) I B) II C) III D) IV E) V252Topic: Ether Reactions Section: 11.12A Difficulty Level: Medium119. What would be the major product(s) of the following reactionC6H5CH2OCH3 ? heatConcd. HBr (xs)A) C6H5Br + CH3OHB) C6H5CH2Br + CH3BrC) C6H5CH2OH + CH3BrD) C6H5CH2Br + CH3OHE) C6H5CH2CH2BrTopic: Ether Reactions Section: 11.12A Difficulty Level: Medium120. What would be the major product(s) of the following reactionO 1 equiv. HBr(conc)?heatA) C6H5Br + CH3OHB) C6H5CH2Br + CH3BrC) C6H5CH2OH + CH3BrD) C6H5CH2Br + CH3OHE) C6H5CH2CH2Br253Topic: Epoxide Synthesis Section: 11.13 Difficulty Level: Medium121. If cis-2-butene is treated with meta-chloroperbenzoic acid what is the final product?OH3C CH3H HOH3C HH CH3OH3C HH3C HOH3CH2C HH HI II III IVA) IB) IIC) IIID) IVE) None of the aboveTopic: Epoxide Synthesis Section: 11.13 Difficulty Level: Medium122. If trans-2-butene is treated with meta-chloroperbenzoic acid what is the final product?OH3C CH3H HOH3C HH CH3OH3C HH3C HOH3CH2C HH HI II III IVA) IB) IIC) IIID) IVE) None of the above254Topic: Epoxide Synthesis Section: 11.13 Difficulty Level: Medium123. If (Z)-2-pentene is treated with meta-chloroperbenzoic acid what is the final product?OH3CH2C CH3H HOH3CH2C HH CH3OH3CH2C HH3C HI II IIIA) IB) IIC) IIID) All of the aboveE) None of the aboveTopic: Epoxide Synthesis Section: 11.13 Difficulty Level: Medium124. If (E)-2-pentene is treated with meta-chloroperbenzoic acid what is the final product?OH3CH2C CH3H HOH3CH2C HH CH3OH3CH2C HH3C HI II IIIA) IB) IIC) IIID) All of the aboveE) None of the above255Topic: Epoxide Reactions, Isotope Labeling Section: 11.14Difficulty Level: Medium125. Select the structure of the major product formed in the following reaction.CH3CHOCH2 HAH218O?A) CH3CH2CH218OHB) CH3CHCH318OH C) CH3CHCH2OH18OH D) CH3CHOHCH218OH E) CH3CHCH218OH18OHTopic: Ether Reactions Section: 11.14 Difficulty Level: Medium126. Heating 2-ethoxyhexane with excess concentrated HBr would produce:A) CH3CH2OCH2CH2CH2CH2CH2CH2BrB) BrCH2CH2OCH2CH2CH2CH2CH2CH3C) CH3CH2OH and CH3CH2CH2CH2CHBrCH3D) CH3CH2Br and CH3CH2CH(OH)CH2CH2CH3E) CH3CH2Br and CH3CH2CH2CH2CHBrCH3256Topic: Ether Reactions Section: 11.14 Difficulty Level: Medium127. Heating 2-ethoxyhexane with one equivalent of concentrated HBr would produce:A) CH3CH2OCH2CH2CH2CH2CH2CH2BrB) BrCH2CH2OCH2CH2CH2CH2CH2CH3C) CH3CH2OH and CH3CH2CH2CH2CHBrCH3D) CH3CH2Br and CH3CH2CH(OH)CH2CH2CH3E) CH3CH2Br and CH3CH2CH2CH2CH(OH)CH3Topic: Ether Reactions Section: 11.14 Difficulty Level: Medium128. Heating 2-ethoxyhexane with one equivalent of concentrated HI would produce:A) CH3CH2OCH2CH2CH2CH2CH2CH2IB) ICH2CH2OCH2CH2CH2CH2CH2CH3C) CH3CH2OH and CH3CH2CH2CH2CHICH3D) CH3CH2I and CH3CH2CH(OH)CH2CH2CH3E) CH3CH2I and CH3CH2CH2CH2CH(OH)CH3Topic: Epoxide Reactions Section: 11.14 Difficulty Level: Medium129. Epoxidation followed by reaction with aqueous base converts cyclopentene into whichof these?I II III IVH O HH O HH O HOHHH O HH O HOHHA) IB) IIC) IIID) IVE) Equal amounts of III and IV257Topic: Epoxide Reactions Section: 11.14 Difficulty Level: Medium130. What would be the major product of the following reaction sequence?O?CH3OCH3OHOH OCH3 OCH3 OCH3 OCH3 OH OH OHI II III IVH3O+A) IB) IIC) IIID) IVE) Equal amounts of II and IVAns ATopic: Epoxide Reactions Section: 11.14 Difficulty Level: Medium131. What would be the major product of the following reaction sequence?OH+ CH3OH ?OH OCH3 OCH3 OCH3 OCH3 OH OH OHI II III IVA) IB) IIC) IIID) IVE) Equal amounts of II and IVAns C258Topic: Epoxide Synthesis/Reactions Section: 11.13 and 11.14 132. cis-3-Hexene is treated with meta-chloroperbenzoic acid and the product is thensubjected to acid-catalyzed hydrolysis. What is the final product?CH2CH3 CH2CH3 CH2CH3OH H HO CH2CH3H HH OHI IICH2CH3H HHO HCH2CH3HO HIII IVCH2CH3CH2CH3HH OHCH V2CH3CH2CH3H OHH OHA) equal amounts I and IIB) equal amounts I, II and VC) equal amounts III, IV and VD) equal amounts III and IVE) Only VTopic: Epoxide Synthesis/Reactions Section: 11.13 and 11.14 133. trans-3-Hexene is treated with meta-chloroperbenzoic acid and the product is thensubjected to acid-catalyzed hydrolysis. What is the final product?CH2CH3 CH2CH3 CH2CH3OH H HO CH2CH3H HH OHI IICH2CH3H HHO HCH2CH3HO HIII IVCH2CH3CH2CH3HH OHCH V2CH3CH2CH3H OHH OHA) equal amounts I and IIB) equal amounts I, II and VC) equal amounts III, IV and VD) equal amounts, III and IVE) Only V259Topic: Epoxide Synthesis and ReactionsSection: 11.13A and 11.14Difficulty Level: Medium134. What would be the final product?H3CC CH2CH3RCOOHOproduct CH3OH, HA final productA) (CH3)2CHCH2OCH3 B) (CH3)2CCH3OCH3 C) (CH3)2CCH2OHOCH3 D) (CH3)2CCH2OCH3OH E) (CH3)2CCH2OCH3OCH3Topic: Epoxide Synthesis/Reactions Section: 11.13A and 11.14 Difficulty Level: Medium135. What would be the major product of the following reaction sequence??I II III IVRCOOOH NH3O OH OH OH NH2 NH2 OHA) IB) IIC) IIID) IVE) Equal amounts of II and IVAns C260Topic: Epoxide Reactions Section: 11.15 136. Which compound (or compounds) would be produced when trans-2-butene is treated first with a peroxy acid to form an epoxide, and then the epoxide is subjected to acidcatalyzed hydrolysis?C CHO CH3H CH3H O HIC CHO HHO CH3CH3H IIC CH OHH3C HCH3OHIIIA) An equimolar mixture of I and IIB) An equimolar mixture of II and IIIC) I aloneD) II aloneE) III alone261Topic: Epoxide Reactions Section: 11.15 137. Which compound (or compounds) would be produced when cis-2-butene is treated first with a peroxy acid to form an epoxide, and then the epoxide is subjected to acidcatalyzed hydrolysis?C CHO CH3H CH3H O HIC CHO HHO CH3CH3H IIC CH OHH3C HCH3OHIIIA) An equimolar mixture of I and IIB) An equimolar mixture of II and IIIC) I aloneD) II aloneE) III aloneTopic: Nomenclature Section: 11.16 138. What is the correct IUPAC name for the following compound?OOOOOA) 15-crown-5B) 15-crown-4C) 5-crown-15D) 15-crown-15E) Cyclopentadecane pentaether262Topic: Nomenclature Section: 11.16 139. What is the correct IUPAC name for the following compound?OOOOA) 12-crown-5B) 12-crown-4C) 4-crown-12D) 12-crown-12E) Cyclododecane tetraetherSHORT ANSWER QUESTIONSTopic: Isomers Section: 11.1A Difficulty Level: Medium140. Draw all of the primary alcohols corresponding to the formula C5H12O, includingstereoisomers. OH OHOH OHHOHH263Topic: Isomers Section: 11.1A Difficulty Level: Medium141. Draw all of the enantiomeric forms corresponding to the formula C5H12O.OHHOHH HO H HO HHO H HO HTopic: Isomers Section: 11.1A Difficulty Level: Medium142. Draw all the enantiomeric forms of ethers with the formula C5H12O.OHOHTopic: Nomenclature Section: 11.1A 143. Give the correct IUPAC name corresponding to the following structure:OH (R)-3-ethyl-2-methyl-3-hexanol264Topic: Nomenclature Section: 11.1A 144. Give the correct IUPAC name corresponding to the following structure:CH3OHBr H (1R,2R)-2-bromo-1-methylcyclopentanolTopic: Nomenclature Section: 11.1A 145. Give the correct IUPAC name corresponding to the following structure:OH 6-cyclohexyl-2,7-dimethyl-3-octanolTopic: Isomerism Section: 11.1B Difficulty Level: Easy146. Draw structures for all possible ethers having the formula C4H10O C4H10O: ethersO O OTopic: Isomers Section: 11.1B Difficulty Level: Medium147. Draw all of the ethers corresponding to the formula C5H12O, including stereoisomers.O O OOOHOHO265Topic: Nomenclature Section: 11.1B 148. Give the correct IUPAC name corresponding to the following structure:O O 1,3-diethoxyhexaneTopic: Ether Reactivity Section: 11.3D Difficulty Level: Easy149. Long-term storage of ethers can be dangerous, because most ethers react slowly with oxygen by a radical process called __________________. This process forms peroxides and hydroperoxides which are dangerously _______________.utooxidation, explosiveTopic: General, Alcohol Synthesis Section: 11.4Difficulty Level: Easy150. We have learned three different methods to convert alkenes into alcohols.a. The method that takes place with Markovnikov regioselectivity but is prone torearrangement is ________________.b. The method that takes place with Markovnikov regioselectivity and does not lead torearrangement is _____________.c. The method that takes place with anti-Markovnikov regioselectivity and synstereoselectivity is _______________.. acid-catalyzed hydration; b. oxymercuration-demercuration; c. hydroborationoxidation266Topic: Alcohol Synthesis/Mechanism Section: 11.4Difficulty Level: Medium151. What reaction is needed to accomplish the following transformation:H3O+OH Oxymercuration/demurcurationTopic: Alcohol Synthesis/Mechanism Section: 11.4152. Propose a mechanism for the following transformation:H3O+OHH+H2OOHH-H+OH267Topic: Alcohol Synthesis Section: 11.4153. Draw the structures of all the products formed when (3R)-3-methylcyclopentene issubjected to the hydroboration-oxidation sequence. The alkene is symmetrically substituted: thus, Markovnikov rule does not apply. Hence, all four products shown below are likely to be formed in roughly equal proportions.H3C H(3R)-3-methylcyclopentenehydroboration-oxidationH3C H H3C H H3C H H3C HOH OHOH OH+ + +Topic: Alcohol Synthesis Section: 11.4154. Draw the products formed from the oxymercuration-demercuration of 3-methylcyclopentene. OHOHand268Topic: General, Alcohol Reactions Section: 11.5Difficulty Level: Easy155. Reactions of alcohols can be broadly categorized into three types.a. Those that utilize the hydroxyl oxygen as a ____________.b. Those that utilize the hydroxyl proton as an _________.c. Those that convert the hydroxyl group into a _____________. nucleophile or base; b. acid; c. leaving groupTopic: Alcohol as Acids Section: 11.6 Difficulty Level: Easy156. Finish the following acid-base reaction and predict if it will proceed in the forward direction:OH + NaNH2OH + NaNH2 ONa + NH3pKa = 18 pKa = 35YesTopic: Alcohol as Acids Section: 11.6 Difficulty Level: Easy157. Finish the following acid-base reaction and predict if it will proceed in the forward direction:OH + Na+ C CHOH + Na+ C CH ONa + HC CHpKa = 18 pKa = 25Yes269Topic: Alcohol as Acids Section: 11.6 Difficulty Level: Easy158. Finish the following acid-base reaction and predict if it will proceed in the forward direction:OH + CH3COONaOH + CH3COONa ONa + CH3COOHpKa = 18pKa = 5NoTopic: General Section: 11.9Difficulty Level: Medium159. When an alcohol in which the OH is attached to a stereogenic carbon reacts with thionyl chloride (SOCl2) in the presence of a 3° amine, the resulting alkyl chloride is produced with _____________ of configuration. inversionTopic: General Section: 11.10 Difficulty Level: Easy160. Stereochemically speaking, conversion of an alcohol into a tosylate occurs with_____________ of configuration. retention270Topic: Multistep ReactionsSection: 11.10Difficulty Level: Medium 161. Complete the following reaction sequence, giving structures for compounds C and D:OHDMFCH3SO2Cl C CH3OH DNa2CO3C =OMsD==OCH3Topic: Multistep Reactions Section: 11.10Difficulty Level: Medium162. Supply the missing reagents A and B.CH3OHCH3OTsA BCH3CNA pCH3C6H4SO2Cl, base B NaCN in ehtanolTopic: General Section: 11.11B Difficulty Level: Easy163. The SN2 reaction between an alkoxide and an alkyl halide is commonly referred to as the_________________ synthesis. WilliamsonTopic: Ether Synthesis Section: 11.11B Difficulty Level: Easy164. Which is the most efficient way to prepare isopropyl methyl ether via the Williamsonmethod?H3I + (CH3)2CHONa271Topic: Ether Synthesis/Mechanism Section: 11.11BDifficulty Level: Medium165. Propose a mechanism for the following transformation:HOBr -OHOOBr-OHH OBrOTopic: Ether Synthesis Section: 11.11B Difficulty Level: Medium166. Predict the product of the following reaction:HOBr -OHO272Topic: Ether Synthesis/Mechanism Section: 11.11BDifficulty Level: Medium167. Propose a mechanism for the following transformation:HO Br -OHOO-OHOH Br O BrTopic: Ether Synthesis/Mechanism Section: 11.11BDifficulty Level: Medium168. Propose a mechanism for the following transformation:HOBr -OHOOBr-OHH OBrO273Topic: Ether Synthesis/Mechanism Section: 11.11BDifficulty Level: Medium169. Propose a mechanism for the following transformation:OHBrOHOOBrH OHOBrOTopic: Ether Synthesis Section: 11.11B Difficulty Level: Medium170. Which is the best method to prepare ethoxycyclopentane via the Williamson method? ONaI O +274Topic: Ether Synthesis/Mechanism Section: 11.11BDifficulty Level: Medium171. Propose a mechanism for the following transformation:O1 equiv. HIheatI+ CH3OHOH IO HCH2-CH3OHIITopic: Multistep Reactions Section: 11.6 and 11.11B Difficulty Level: Medium172. Complete the following reaction sequence, giving structures for compounds A and B:OHNaoDMFCH3Br A B-H2A =ONaB==OCH3275Topic: Multistep Reactions Section: 11.11C Difficulty Level: Medium173. Supply the missing reagents A and B.A B OC(CH3)3A = Hg(OAc)2, THF, HOC(CH3)3 B = NaBH4Topic: General Section: 11.13 Difficulty Level: Easy174. Three-membered rings containing oxygen are called _______________ or______________. oxiranes; epoxidesTopic: General Section: 11.13B Difficulty Level: Medium175. A reaction which leads to a product of particular stereoisomeric outcome, depending onthe stereochemistry of the reactant, is termed_________________. stereospecificTopic: Epoxide Synthesis and Reactions Section: 11.13 and 11.14176. Provide a reasonable synthetic strategy for the synthesis of trans-1,2-cyclohexanediol from bromocyclohexane Ans: BrCH3ONa m-CPBA H3O+CH3OHOOHOH+ enantiomer276Topic: Epoxide Synthesis and Reactions Section: 11.13 and 11.14177. Provide a reasonable synthetic strategy for the synthesis of trans-2-methoxycyclopentanol from bromocyclopentane CH3ONaCH3OHm-CPBABrOCH3ONaCH3OHOHOCH3+ enantiomerTopic: General Section: 11.16 Difficulty Level: Medium178. The development of a procedure called __________________ has made the use ofnonpolar solvents possible in reactions involving polar reagents. phase transfer catalysisTopic: General Section: 11.16 Difficulty Level: Medium179. The relationship between a crown ether and the ion it transports is known as the____________________ relationship. guest-hostTopic: General Section: 11.16 Difficulty Level: Medium180. A compound or ion that prefers a nonpolar environment to an aqueous one is said to be______________. lipophilic277Topic: Spectroscopy of Alcohols Section: VariousDifficulty Level: Medium181. Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown:C3H8OIR – 3350cm-1, strong, broad 6H doublet at 1.3 , J = 7 Hz1H singlet at 2.2 , (exchangeable) 1H septet at 4.0 , J = 7 HzOHTopic: Spectroscopy of Ethers Section: VariousDifficulty Level: Medium182. Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown:C4H10OIR – 1125cm-1, strong, broad 6H triplet at 1.2 , J = 7 Hz 4H quartet at 3.7 , J = 7 HzO278Topic: Spectroscopy of Ethers Section: VariousDifficulty Level: Medium183. Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown:C6H14OIR – 1120cm-1, strong, broad 6H triplet at 0.9 4H sextet at 1.5 4H triplet at 3.4 OTopic: Spectroscopy of Alcohols Section: VariousDifficulty Level: Medium184. Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown:C7H8OIR – 3325cm-1, strong, broad1H broad singlet at 2.3 (exchangeable)2H singlet at 4.6 5H multiplet at 7.3 OH279Topic: Multistep Synthetic Strategy Section: Various185. Provide a reasonable synthetic strategy for the synthesis of a racemic mixture of(1R,2R) and (1S,2S)-2-bromo-1-methylcyclopentanol from methylcyclopentane:CH3OHBr HCH3BrBr2hCH3ONaCH3OH heatCH3OHBr H+Br2, H2O2-bromo-1-methylcyclopentanol(1R,2R) (1S,2S)CH3 CH3Topic: Multistep Synthetic Strategy Section: Various186. Provide a reasonable synthetic strategy for the synthesis of a racemic mixture of (1R,2R) and(1S,2S)-2-bromo-1-methylcyclopentanol from methylenecyclopentane:HBrBrNaOCH3HOCH3OHBrH+ enantiomerBr2H2O280Topic: Multistep Reactions Section: Various 187. Complete the following reaction sequence, giving structural details of all keyintermediates:i) Li, NH3 ii) KMnO4 ,OH, H2O iii) H3O+?LiNH3i) KMnO4 ,OH, H2Oii) H3O+OHOHHHHHHOHO+(2S,3S)-pentane-2,3-diol (2R,3R)-pentane-2,3-diol281Topic: Multistep Reactions Section: Various 188. Complete the following reaction sequence, giving structural details of all key intermediates:i) P-2, H2ii) KMnO4 ,OH, H2O iii) H3O+?P-2, H2i) KMnO4 ,OH, H2Oii) H3O+OHHHHOHOHHOH+(2S,3R)-pentane-2,3-diol (2R,3S)-pentane-2,3-diolTopic: Multistep Reactions Section: Various 189. Complete the following reaction sequence, giving structural details of all key intermediates:i) Lindlar catalyst, H2ii) KMnO4 ,OH, H2Oiii) H3O+? Lindlar catalyst H2i) KMnO4 ,OH, H2Oii) H3O+OHHHHOHOHHOH+(2S,3R)-pentane-2,3-diol (2R,3S)-pentane-2,3-diol282Topic: Multistep Reactions Section: Various 190. Complete the following reaction sequence, giving structural details of all key intermediates:i) Lindlar catalyst, H2ii) OsO4 iii) NaHSO3?i) Lindlar catalystH2ii) OsO4 iii) NaHSO3OHHHHOHOHHOH+(2S,3R)-pentane-2,3-diol (2R,3S)-pentane-2,3-diolTopic: Multistep Reactions Section: Various 191. Complete the following reaction sequence, giving structural details of all keyintermediates:i) H2, Lindlar catalystii) KMnO4 ,OH, H2Oiii) H3O+?i) KMnO4 ,OH, H2Oii) H3O+OHHHHOmesoH2 Lindlar catalyst283Topic: Multistep Reactions Section: Various 192. Complete the following reaction sequence, giving structural details of all keyintermediates:i) H2, P-2ii) KMnO4 ,OH, H2O iii) H3O+ ?i) KMnO4 ,OH, H2Oii) H3O+OHHHHOmesoH2, P-2Topic: Multistep Reactions Section: Various 193. Complete the following reaction sequence, giving structural details of all keyintermediates:i) Li, NH3ii) m-CPBA iii) H3O+, H2O ?LiNH3HOHHOHOHHHHOi +) m-CPBAii) H3O+, H2O(2R,3S)-pentane-2,3-diol (2S,3R)-pentane-2,3-diol284Topic: Spectroscopy of Ethers Section: Various194. Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown:C6H14OIR – 1120cm-1, strong, broad 3H triplet at 1.1 9H singlet at 1.15 2H quartet at 3.45  Topic: Spectroscopy of Ethers Section: Various195. A compound has the formula C5H10, with the 13C and 1H NMR spectral data shown. Propose structure that fits this data.13C NMRBroadband decoupled 13C NMR: 23.5, 26.7, 68.9 δ DEPT-90: no peaksDEPT-135: no positive peaks; negative peaks at 23.5, 26.7, 68.9 δ1H NMR1.7 δ, multiplet (6H)3.72 δ, triplet (4H) J = 7Hz O286Topic: Spectroscopy of Alcohols Section: Various196. A compound has the formula C6H14O. The 13C and 1H NMR spectral data for this compound are:13C NMRBroadband decoupled 13C NMR: 29.7, 29.8, 46.4, 60.0 δ DEPT-90: no peaksDEPT-135: positive peak at 29.8 δ; negative peaks at 29.7, 60.0 δ 1H NMR0.91 δ, singlet (9H)1.53 δ, triplet (2H) J = 7.3Hz2.13 δ, broad singlet (exchangeable, 1H)3.70 δ, triplet (2H) J = 7.3Hz