Package Title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 17 Question type: Multiple choice 1) Which of the following is the best name
... [Show More] for the following compound? O O a) Isobutyl ethanoate b) Ethyl isopropanoate c) 3-methylbutyl ethanoate d) Ethoxy isobutyl ketone e) Ethyl 3-methylbutanoate Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 2) The correct structure for ethyl 3-methylbutanoate is: O O O O O O O O O O I II III IV V a) I b) II c) III d) IV e) V 1 Contact: [email protected] Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 3) The correct structure for bicyclo[1.1.1]pentane-2-carboxylic acid is: a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 4) The correct structure for bicyclo[2.2.2]octane-2-carboxylic acid is: 2 a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 5) The correct structure for bicyclo[1.1.0]butane-2-carboxylic acid is: a) I b) II c) III d) IV e) V Answer: E 3 Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 6) The correct structure for methyl bicyclo[1.1.1]pentane-2-carboxylate is: a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 7) The correct structure for methyl bicyclo[2.2.2]octane-2-carboxylate is: 4 a) I b) II c) III d) IV e) V Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 8) The correct structure for methyl bicyclo[1.1.0]butane-2-carboxylate is: a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 9) The correct structure for methyl bicyclo[2.2.2]octane-1-carboxylate is: 5 a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 10) A correct name for O O is: a) 2-Methylbutyl 2-methylbutanoate b) 2-Methylbutyl 3-methylbutanoate c) 3-Methylbutyl isovalerate d) Isopentyl isovalerate e) Isopentyl isobutyrate Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 11) The correct structure for ethyl 3-methylbutanoate is: 6 O O O O O O O O O O I II III IV V a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 12) What is the IUPAC name for Cl Cl O a) ∝-Chlorovaleryl chloride b) 2-Chloropentanoyl chloride c) 1-Chloropentanoyl chloride d) 1,2-Dichloropentanal e) 1-Chloro-1-butanecarbonyl chloride Answer: B Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 13) The correct structure for ethyl 2-chloropentanoyl chloride is: 7 OH O OH O OH O Cl O I II III IV V Cl Cl Cl Cl Cl O Cl a) I b) II c) III d) IV e) V Answer: E Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 14) What is the IUPAC name for O O a) 2,3−Dimethylbutyl acetate b) 2,3−Dimethyl-4-oxoethanal c) 2,3−Dimethylbutyl methanoate d) 2,3−Dimethylbutyl methylate e) 2,3−Dimethylbutyl formylate Answer: C Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 15) The correct structure for ethyl 2,3−dimethylbutyl methanoate is: 8 H O O H O O H O O O O O O I II III IV V a) I b) II c) III d) IV e) V Answer: A Topic: Nomenclature Section: 17.2 Difficulty Level: Medium 16) Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide? N O III H N O I N O II N O IV V N O a) I b) II c) III d) IV 9 e) V nswer: E clature ifficulty Level: Medium ate? A Topic: Nomen Section: 17.2 D 17) Which of the following structures is 3,4-dimethylpentyl chloroform H O O Cl I Cl O O II Cl O O III O O Cl Cl O O IV V ) V nswer: E clature ifficulty Level: Hard 8) Which compound would be the strongest acid? H ) CH3CH2CCl2CO2H nswer: E a) I b) II c) III d) IV e A Topic: Nomen Section: 17.9 D 1 a) CHCl2CH2CH2CO2H b) ClCH2CHClCH2CO2 c) CH3CCl2CH2CO2H d) CH3CHClCHClCO2H e A Topic: Acidity Section: 17.2 10 Difficulty Level: Easy 9) Which compound would be the weakest acid? H ) CH3CH2CCl2CO2H nswer: A ifficulty Level: Easy 0) Which compound would be the strongest acid? ) 2,2-dichlorobutanoic acid nswer: E ifficulty Level: Medium 1) Which compound would be expected to have the lower pKa? ) 2,2-dichlorobutanoic acid nswer: E ifficulty Level: Medium 1 a) CHCl2CH2CH2CO2H b) ClCH2CHClCH2CO2 c) CH3CCl2CH2CO2H d) CH3CHClCHClCO2H e A Topic: Acidity Section: 17.2 D 2 a) 4,4-dichlorobutanoic acid b) 3,4-dichlorobutanoic acid c) 3,3-dichlorobutanoic acid d) 2,3-dichlorobutanoic acid e A Topic: Acidity Section: 17.2 D 2 a) 4,4-dichlorobutanoic acid b) 3,4-dichlorobutanoic acid c) 3,3-dichlorobutanoic acid d) 2,3-dichlorobutanoic acid e A Topic: Acidity Section: 17.2 D 11 22) Which compound would be expected to have the higher pKa? ) 2,2-dichlorobutanoic acid nswer: A ifficulty Level: Medium 3) Which compound would be the weakest acid? ) 2,2-dichlorobutanoic acid nswer: A ifficulty Level: Medium 4) Which compound would be the strongest acid? cid e ) ethanol nswer: B ifficulty Level: Medium a) 4,4-dichlorobutanoic acid b) 3,4-dichlorobutanoic acid c) 3,3-dichlorobutanoic acid d) 2,3-dichlorobutanoic acid e A Topic: Acidity Section: 17.2 D 2 a) 4,4-dichlorobutanoic acid b) 3,4-dichlorobutanoic acid c) 3,3-dichlorobutanoic acid d) 2,3-dichlorobutanoic acid e A Topic: Acidity Section: 17.2 D 2 a) water b) acetic a c) ethane d) acetylen e A Topic: Acidity Section: 17.2 D 12 25) Which compound would be the weakest acid? cid e ) ethanol nswer: C ifficulty Level: Medium 6) Which compound would be expected to have the higher pKa? cid e ) ethanol nswer: C ifficulty Level: Medium 7) Which compound would be expected to have the lower pKa? cid e ) ethanol nswer: B ifficulty Level: Medium a) water b) acetic a c) ethane d) acetylen e A Topic: Acidity Section: 17.2 D 2 a) water b) acetic a c) ethane d) acetylen e A Topic: Acidity Section: 17.2 D 2 a) water b) acetic a c) ethane d) acetylen e A Topic: Acidity Section: 17.2 D 13 28) In which of the following sequences are the compounds listed in order of decreasing acidity? ) CH3CH2OH > H2O > CH3COOH > HC≡CH > NH3 nswer: A ifficulty Level: Medium 9) In which of the following sequences are the compounds listed in order of increasing acidity? ) NH3 < H2O < CH3COOH < HC≡CH < CH3CH2OH nswer: A ifficulty Level: Medium 0) In which of the following sequences are the compounds listed in order of decreasing acidity? ) PhOH > H2O > CH3COOH > HC≡CH > NH3 nswer: C ifficulty Level: Medium a) CH3COOH > H2O > CH3CH2OH > HC≡CH > NH3 b) CH3CH2OH > CH3COOH > H2O > HC≡CH > NH3 c) CH3COOH > CH3CH2OH > H2O > NH3 > HC≡CH d) H2O > CH3COOH > CH3CH2OH > HC≡CH > NH3 e A Topic: Acidity Section: 17.2 D 2 a) NH3 < HC≡CH < CH3CH2OH < H2O < CH3COOH b) CH3CH2OH < NH3 < H2O < HC≡CH < CH3COOH c) CH3COOH < CH3CH2OH < H2O < NH3 < HC≡CH d) H2O < CH3COOH < CH3CH2OH < HC≡CH < NH3 e A Topic: Acidity Section: 17.2 D 3 a) CH3COOH > H2O > PhOH > HC≡CH > NH3 b) PhOH > CH3COOH > H2O > HC≡CH > NH3 c) CH3COOH > PhOH > H2O > HC≡CH > NH3 d) H2O > CH3COOH > PhOH > HC≡CH > NH3 e A Topic: Acidity Section: 17.2 D 14 31) In which of the following sequences are the compounds listed in order of decreasing acidity? ) PhCOOH > H2O > PhOH > PhH > PhCH2OH nswer: B ifficulty Level: Medium a) PhCOOH > H2O > PhOH > PhCH2OH > PhH b) PhCOOH > PhOH > H2O > PhCH2OH > PhH c) PhH > H2O > PhOH > PhCH2OH > PhCOOH d) PhOH > H2O > PhCOOH > PhCH2OH > PhH e A Topic: Acidity Section: 17.2 D 32) Which of the following would be the strongest acid? I II III Cl CO2H Cl CO2H Cl CO2H CO2H Cl Cl CO2H Cl Cl IV V ) V nswer: C ifficulty Level: Medium 33) Which of the following would be the weakest acid? a) I b) II c) III d) IV e A Topic: Acidity Section: 17.2 D 15 I II III Cl CO2H IV V Cl CO2H Cl CO2H CO2H Cl Cl CO2H Cl Cl a) I b) II c) III d) IV e) V Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium 34) Which of the following would be the strongest acid? I II III F CO2H IV V F CO2H F CO2H CO2H F F CO2H F F a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium 16 35) Which of the following would be the strongest acid? I II III F CO2H IV V Cl CO2H Cl CO2H CO2H Cl F CO2H F F a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium 36) Which of the following would be the strongest acid? I II III NO2 CO2H IV V NO2 CO2H O2N CO2H CO2H O2N NO2 CO2H NO2 O2N a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 17 Difficulty Level: Medium 37) Which of the following would be the strongest acid? I II III CH3 CO2H IV V CH3 CO2H H3C CO2H CO2H H3C CH3 CO2H CH3 H3C a) I b) II c) III d) IV e) V Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium 38) Which of the following would be the strongest acid? I II III OCH3 CO2H IV V OCH3 CO2H H3CO CO2H CO2H H3CO OCH3 CO2H OCH3 H3CO a) I b) II c) III d) IV e) V Answer: A 18 Topic: Acidity Section: 17.2 Difficulty Level: Medium 39) Which of the following would be the weakest acid? I II III OCH3 CO2H IV V OCH3 CO2H H3CO CO2H CO2H H3CO OCH3 CO2H OCH3 H3CO a) I b) II c) III d) IV e) V Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium 40) Which of the following would be the weakest acid? I II III CH3 CO2H IV V CH3 CO2H H3C CO2H CO2H H3C CH3 CO2H CH3 H3C a) I b) II c) III d) IV e) V 19 Answer: C Topic: Acidity Section: 17.2 Difficulty Level: Medium 41) Which of the following acids would have the smallest value for pKa? a) BrCH2CH2CH2COOH b) ClCH2CH2CH2COOH c) Cl2CHCH2CH2COOH d) ICHBrCH2CH2COOH e) BrCCl2CH2CH2COOH Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium 42) Which of the following acids would be expected to have the smallest value for pKa? a) 4-bromobutanoic acid b) 4-chlorobutanoic acid c) 4,4-dichlorobutanoic acid d) 4-bromo-4-iodobutanoic acid e) 4-bromo-4,4-dichlorobutanoic acid Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium 43) Which of the following acids would have the largest value for pKa? a) BrCH2CH2CH2COOH b) ClCH2CH2CH2COOH c) Cl2CHCH2CH2COOH d) ICHBrCH2CH2COOH e) BrCCl2CH2CH2COOH Answer: A 20 Topic: Acidity Section: 17.2 Difficulty Level: Medium 44) Which of the following acids would be expected to have the largest value for pKa? a) 4-bromobutanoic acid b) 4-chlorobutanoic acid c) 4,4-dichlorobutanoic acid d) 4-bromo-4-iodobutanoic acid e) 4-bromo-4,4-dichlorobutanoic acid Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium 45) Which of the following acids would have the smallest value for pKa1? a) HOOCCH2CH2CH2CH2CH2COOH b) HOOCCH2CH2CH2CH2COOH c) HOOCCH2CH2CH2COOH d) HOOCCH2CH2COOH e) HOOCCH2COOH Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium 46) Which compound would be most acidic? a) OH O b) OH 21 c) OH d) O e) O H H Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Medium 47) In which of the following are the compounds listed in order of decreasing acidity? a) CH3CO2H > CH3CH2OH > C6H5OH > H2O b) C6H5OH > CH3CO2H > H2O > CH3CH2OH c) CH3CO2H > H2O > C6H5OH > CH3CH2OH d) H2O > CH3CO2H > C6H5OH > CH3CH2OH e) None of these choices. Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium 48) In which of the following are the compounds listed in order of decreasing acidity? a) CH3CO2H > CH3CH2OH > C6H5OH > H2O b) C6H5OH > CH3CO2H > H2O > CH3CH2OH c) CH3CO2H > H2O > C6H5OH > CH3CH2OH d) H2O > CH3CO2H > C6H5OH > CH3CH2OH e) CH3CO2H > C6H5OH > CH3CH2OH > H2O Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Medium 22 49) Which of the following would be the strongest acid? a) Benzoic acid b) 4-Nitrobenzoic acid c) 4-Methylbenzoic acid d) 4-Methoxybenzoic acid e) 4-Iodobenzoic acid Answer: B Topic: Acidity Section: 17.2 Difficulty Level: Hard 50) Which of the following acids would be expected to have the smallest value for pKa? a) Benzoic acid b) 4-Nitrobenzoic acid c) 4-Methylbenzoic acid d) 4-Methoxybenzoic acid e) 4-Iodobenzoic acid Answer: B Topic: Acidity Section: 17.2 Difficulty Level: Hard 51) Which of the following would be the weakest acid? a) Benzoic acid b) 4-Nitrobenzoic acid c) 4-Methylbenzoic acid d) 4-Methoxybenzoic acid e) 4-Iodobenzoic acid Answer: D Topic: Acidity Section: 17.2 Difficulty Level: Hard 23 52) Which of the following acids would be expected to have the largest value for pKa? a) Benzoic acid b) 4-Nitrobenzoic acid c) 4-Methylbenzoic acid d) 4-Methoxybenzoic acid e) 4-Iodobenzoic acid Answer: D Topic: Acidity Section: 17.2 Difficulty Level: Hard 53) Which of the following would be the strongest acid? a) 2,3-Dimethylhexanoic acid b) 3,3-Diiodopentanoic acid c) 3-Iodo-4-bromopentanoic acid d) 3-Chloro-4-bromohexanoic acid e) 2-Fluoro-4-bromopentanoic acid Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Hard 54) Which of the following acids would be expected to have the smallest value for pKa? a) 2,3-Dimethylhexanoic acid b) 3,3-Diiodopentanoic acid c) 3-Iodo-4-bromopentanoic acid d) 3-Chloro-4-bromohexanoic acid e) 2-Fluoro-4-bromopentanoic acid Answer: E Topic: Acidity Section: 17.2 Difficulty Level: Hard 55) Which compound would be most acidic? 24 a) Acetic acid b) Ethanol c) Phenol d) Acetone e) Water Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Hard 56) Which of the following acids would be expected to have the smallest value for pKa? a) Acetic acid b) Ethanol c) Phenol d) Acetone e) Water Answer: A Topic: Acidity Section: 17.2 Difficulty Level: Hard 57) The IR spectrum of a compound exhibits a broad absorption band at 2500-3000 cm-1 and a sharp band at 1710 cm-1. Which of these compounds could it be? a) 1-Butanol b) Propyl acetate c) Butanoic acid d) Acetyl chloride e) Acetic anhydride Answer: C Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Easy 58) A compound has the molecular formula, C6H12O2. Its IR spectrum shows a strong absorption 25 band near 1740 cm-1; its 1 H NMR spectrum consists of two singlets, at δ 1.4 and δ 2.0. The most likely structure for this compound is: O O O O O H I II III IV V O O O O O a) I b) II c) III d) IV e) V Answer: D Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Medium 59) A compound has the molecular formula, C6H12O2. Its IR spectrum shows a strong absorption band near 1740 cm-1; its 1 H NMR spectrum consists of two singlets, at δ 1.2 and δ 3.6. The most likely structure for this compound is: O O O O I II III IV V O O O O O O a) I b) II c) III d) IV e) V Answer: E Topic: Structure Identification (Spectroscopy) 26 Section: 17.2 Difficulty Level: Medium 60) A compound has the molecular formula C8H14O4. Its IR spectrum shows a strong absorption band near 1740 cm-1. Its 1 H NMR spectrum consists of: triplet, δ 1.3 singlet, δ 2.6 quartet, δ 4.2 The most likely structure for the compound is: IV V O O O O O O O O O O O O I II III HO2C CO2H O O O O a) I b) II c) III d) IV e) V Answer: A Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Medium 61) A compound with the molecular formula C5H10O2 gave the following 1 H NMR spectrum: triplet, δ 0.90 multiplet, δ 1.60 singlet, δ 1.95 triplet, δ 3.95 The IR spectrum showed a strong absorption band near 1740 cm-1. The most likely structure for the compound is: a) O O 27 b) O O c) O O d) OH O e) HO O Answer: A Topic: Structure Identification (Spectroscopy) Section: 17.2 Difficulty Level: Medium 62) A compound with the molecular formula C18H18O4 has a 1 H NMR spectrum that consists of: singlet, δ 2.7 singlet, δ 3.1 multiplet, δ 7.3 The IR spectrum shows a strong absorption band near 1750 cm-1. The most likely structure for the compound is: a) O O C6H5 O O C6H5 b) O O C6H5 O C6H5 O c) OC O C6H5 6H5 O O d) O C6H5 O O C6H5 O e) OC O C6H5 6H5 O O Answer: C Topic: Structure Identification (Spectroscopy) 28 Section: 17.2 Difficulty Level: Medium 63) What would be the product of the following reaction? OH O O H O O O O O O O O O O O I II II III HA + ? 18 18 18 18 18 18 III \ a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 17.7 Difficulty Level: Easy 64) What is the product of this reaction? HN O CO2H H N H2N O O I II III O N H O O O N H O IV V HN HO O ? H2O OHa) I b) II 29 c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.8 Difficulty Level: Easy 65) Predict the major organic product of the reaction sequence, O O O HO O OH O HO O NH2 O H2N O NH2 O HN O O I II III IV V H O O N M i. NH3, H2O ii. dilute HCl, cold a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.8 Difficulty Level: Medium 66) Predict the major organic product of the reaction sequence, 30 O O O i. NH3, H2O ii. dilute H+, cold ? OH OH O O NH2 OH O O NH2 NH2 O O NH O O O NH O I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.8 Difficulty Level: Medium 67) Predict the major organic product of the reaction sequence, O O O HO O NH2 O HN O O I II IV V H O N O III M i. NH3, H2O ii. dilute HCl, cold OH O NH2 O NH2 O NH2 O 31 a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 17.8 Difficulty Level: Medium 68) Predict the major organic product of the reaction sequence, O O O HO O OCH2CH3 O HO O OH O H3CH2CO O OCH2CH3O O H O 3CH2CO O I II III IV V H O 3CH2CO OCH2CH3 M i. CH3CH2OH ii. dilute HCl, cold a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 17.7 Difficulty Level: Medium 69) The product of the following reaction is: 32 I II III IV V O CO2H O O O Cl H O O O CO2H O Cl O O O O OH O O O O O + OH heat (1 mol) (1 mol) ? a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 17.7 Difficulty Level: Medium 70) What is the product of this reaction? O O O CO2H HO O O I II III O O O O O O O IV V O HO O ? CH3OH a) I b) II c) III 33 d) IV ) V nswer: B n Products ifficulty Level: Medium 1) What is the reactant of the following reaction sequence? e A Topic: Reactio Section: 17.7 D 7 i. Mg/ether ii. CO2 iii. H+ OH O ? OH ) O=C(CH2C6H5)2 nswer: C n Products ifficulty Level: Medium 2) Predict the major organic product of the reaction sequence below: a) HCO2CH2C6H5 b) C6H5CH2CO c) C6H5CH2Cl d) C6H5CHClCOOH e A Topic: Reactio Section: 17.3 D 7 I II III IV V OH OH OH CO2H CHO CHO + KMnO4 heat H2O, OH− ? H3O+ a) I 34 b) II c) III d) IV ) V nswer: B n Products ifficulty Level: Medium e A Topic: Reactio Section: 17.3 D 73) What is the expected product, A, of the following reaction sequence? i. NaCN A + NH4 Cl + ii. 70% H2SO4, reflux ) O=C(CH2C6H5)2 nswer: B n Products ifficulty Level: Medium c product of the following reaction? a) HCO2CH2C6H5 b) C6H5CH2COOH c) C6H5CH2OSO3H d) C6H5CHClCOOH e A Topic: Reactio Section: 17.3 D 74) What would be the final organi i. LAH, Et2O ii. H2O Br ? i. Mg, Et2O ii. CO2 + iii. H3O ) (CH ) CCO2CH3 nswer: C ts ifficulty Level: Medium a) (CH3)3CCO2H b) (CH3)3CCOCH3 c) (CH3)3CCH2OH d) (CH3)3COCH3 e 3 3 A Topic: Reaction Produc Section: 12.3 and 17.3 D 35 75) What is the expected product, A, of the following reaction sequence? Cl i. Mg/ether ii. CO2 + A iii. H ) O=C(CH2C6H5)2 nswer: B n Products ifficulty Level: Medium a) HCO2CH2C6H5 b) C6H5CH2COOH c) C6H5CH2OSO3H d) C6H5CHClCOOH e A Topic: Reactio Section: 17.3 D 76) What would be the final organic product of the following reaction? O O 1. LAH 2. H3O+ ? OH OH HO HO OH O OH O I II III V IV a) I b) II c) III d) IV 36 e) V nswer: E ts ifficulty Level: Medium A Topic: Reaction Produc Section: 17.7 and 12.3 D 77) What would be the final organic product of the following reaction? i. DIBAL-H, -78o C ii. H3O+ O O ? OH OH HO HO OH O OH O I II III V IV ) V nswer: D s ifficulty Level: Medium 78) What would be the final organic product of the following reaction? a) I b) II c) III d) IV e A Topic: Reaction Product Section: 16.4 and 17.7 D 37 i. DIBAL-H, -78o C ii. H3O+ ? OH HO OH HO OH I II III IV V O O O O OH a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 16.4 and 17.7 Difficulty Level: Medium 79) What would be the final organic product of the following reaction? 38 i. DIBAL-H, -78o C ii. H3O+ ? I II III IV V O O O O OH O O O OH OH OH O OH a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 16.4 and 17.7 Difficulty Level: Medium 80) What would be the final organic product of the following reaction? 39 ? I II III IV V OH O O NH2 O NHCH3 O DCC CH3NH2 O O OH a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 17.8 Difficulty Level: Medium 81) The product, Z, of the following sequence of reactions is which compound? 40 i. KMnO4, OH− , heat ii. H3O+ iii. SOCl2 iv. CH3CH2OH, base I II III IV V O p-Chlorotoluene Z Cl Cl Cl Cl O O O O O Cl a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.3 and 17.7 Difficulty Level: Medium 82) What would be the final product? CO2H i. PCl5 ii. NH3 iii. P4H10, heat ? a) CH3CH2CH2NH2 b) CH3CH2CONH2 c) CH3CH2CONHCOCH2CH3 d) CH3CH2CN e) CH3CH2COONH4 + Answer: D Topic: Reaction Products Section: 17.5 and 17.8 Difficulty Level: Medium 41 83) What would be the final product of this reaction sequence? I II III V CN NH2 O H N H N O NH2 CO2H IV CO2 NH4 i. PCl3 ii. NH3 iii. P4O10 ? a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 17.5 and 17.8 Difficulty Level: Medium 84) What would be the final product? a) CH3CH2CH2NH2 b) CH3CH2CONH2 c) CH3CH2CONHCOCH2CH3 d) CH3CH2CN e) CH3CH2COCH3 Answer: E 42 Topic: Reaction Products Section: 16.5, 17.5, and 17.8 Difficulty Level: Medium 85) What would be the final product of this reaction sequence? I II III V CN NH2 O H N H N O NH2 CO2H IV COCH3 i. PCl3 ii. NH3 iii. P4O10 iv. CH3Li, ether v. H3O+ ? a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 16.5, 17.5 and 17.8 Difficulty Level: Medium 86) What is the final product of this sequence of reactions? 43 I II III IV V Br O O NH2 CN NH2 NHCl O NH2 O i. SOCl2 ii. excess NH3 ? i. Mg, Et2O ii. CO2 iii. H3O+ a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 17.3, 17.5 and 17.8 Difficulty Level: Medium 87) What is the final product of this sequence of reactions? I II III IV V Br O O NH2 CN NH2 NHCl O NH2 O i. SOCl2 ii. excess NH3 ? i. Mg, Et2O ii. CO2 iii. H3O+ P4O10 heat a) I b) II 44 c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.3, 17.5 and 17.8 Difficulty Level: Medium 88) What is the product of the reaction of 1-propanol with phenyl isocyanate, C6H5N=C=O? a) C6H5 H N O O b) C6H5 N CO2H c) C6H5 N O CHO d) C6H5 H N O O e) C6H5 H N O Answer: A Topic: Reaction Products Section: 17.9 Difficulty Level: Medium 89) What is the ultimate product of this sequence of reactions? Cl N H O IV O C O H N H N O O N H O Cl Cl O I II III O O O V CH3CH2OH CH3NH2 (1 eq.) ? l 45 a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 17.9 Difficulty Level: Medium 90) Identify the product(s) of the following reaction. O CO2H O O OH O CO2H I II III IV V O O CO2H heat ? + CO2 + CO 2 a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 17.10 Difficulty Level: Medium 91) Identify the product(s) of the following reaction. 46 O CO2CH3 O O OH O CO2H I II III IV V O O CO2H heat ? + CO2 + CH3OH + CO 2 H3O+ a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 17.10 Difficulty Level: Medium 92) Identify the product(s) of the following reaction. O COOH heat ? OH COOH O COOH COOH O I II III IV V a) I 47 b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.10 Difficulty Level: Medium 93) Identify the product(s) of the following reaction. a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.10 Difficulty Level: Medium 94) What would be the final organic product of the following reaction? 48 C6H5COCl i. LiAl(OC(CH3)3)3H,-78o C ii. H3O+ ? a) C6H5CO2H b) C6H5CH3 c) C6H5COOCH3 d) C6H5CHO e) C6H5CH2OH Answer: D Topic: Reaction Products Sections: 16.4 and 17.13 Difficulty Level: Medium 95) What would be the final organic product of the following reaction? C6H5COCl i. LiAl(OC(CH3)3)3H ii. H3O+ ? HO OH H+ a) C6H5CH O O b) C6H5CH3 c) C6H5COOCH2CH2OH d) C6H5CHO e) C6H5CH2OH Answer: A Topic: Reaction Products Sections: 16.4, 16.7 and 17.13 Difficulty Level: Medium 96) What would be the final organic product of the following reaction? 49 a) C6H5CH O O b) C6H5CH3 c) C6H5COOCH2CH2OH d) C6H5CHO e) C6H5CH2OH Answer: A Topic: Reaction Products Sections: 16.4, 16.7 and 17.13 Difficulty Level: Medium 97) What would be the final organic product of the following reaction? C6H5COCl i. LiAl(OC(CH3)3)3H ii. H3O+ ? pH 4-5 CH3NH2 a) C6H5CO2H b) C6H5CH2CH2NCH3 c) C6H5CH2CH2CN d) C6H5CH=NCH3 e) C6H5CH2NCH3 Answer: D Topic: Reaction Products Sections: 16.4, 16.8 and 17.13 Difficulty Level: Medium 98) What would be the final organic product of the following reaction? a) C6H5CO2H b) C6H5CH2CH2NCH3 c) C6H5CH2CH2CN d) C6H5CH=NCH3 50 e) C6H5CH2NCH3 Answer: D Topic: Reaction Products Sections: 16.4, 16.8 and 17.13 Difficulty Level: Medium 99) Predict the major organic product, P, of the following sequence of reactions: CO2H Cl Cl O O CO2H O O O O O Cl O O I II III IV V H2 cat. P i. SOCl2 ii. CH3OH i. OH− (2eq.), H2O heat ii. H3O+ a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 17.3 and 17.7 Difficulty Level: Hard 100) What would be the final organic product of the following reaction? 51 a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 16.4 and 17.7 Difficulty Level: Hard 101) What would be the final organic product of the following reaction? 52 a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 16.4 and 17.7 Difficulty Level: Hard 102) What is the expected product, A, of the following reaction sequence? a) HCO2CH2C6H5 b) C6H5CH2COOH c) C6H5CH2OSO3H d) C6H5CHClCOOH e) O=C(CH2C6H5)2 Answer: B 53 Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 103) What is the expected product, A, of the following reaction sequence? i. NaCN ii. 70% H2SO4, reflux A + NH4 Cl + a) Benzyl formate b) Phenylacetic acid c) Benzenesulfonic acid d) 1-chloro-1-phenyl acetic acid e) Dibenzylketone Answer: B Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 104) What is the expected product, A, of the following reaction sequence? a) Benzyl formate b) Phenylacetic acid c) Benzenesulfonic acid d) 1-chloro-1-phenyl acetic acid e) Dibenzylketone Answer: B Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 105) What is the expected product, A, of the following reaction sequence? 54 a) Benzyl formate b) Phenylacetic acid c) Benzenesulfonic acid d) 1-chloro-1-phenyl acetic acid e) Dibenzylketone Answer: B Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 106) What is the reactant of the following reaction sequence? i. NaCN ii. 70% H2SO4, reflux + NH4 COOH + ? a) BrCH2C6H5 b) C6H5CH2COOH c) C6H5CH2OH d) C6H5CH2CH2COOH e) O=C(CH2C6H5)2 Answer: A Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 107) What is the reactant of the following reaction sequence? a) C6H5CH3 b) C6H5CH2COOH c) C6H5CH2OH d) C6H5CH2CH2COOH e) O=C(CH2C6H5)2 Answer: A Topic: Reaction Products Section: 17.3 55 Difficulty Level: Hard 108) What would be the final product, F, of the following sequence of reactions? CO2H Br Br CO2H CO2H CO2H O O I II III IV V i. LAH, Et2O ii. H2O i. Mg, Et2O ii. CO2 iii. H3O+ F PBr3 a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 109) What would be the final product, F, of the following sequence of reactions? CO2H Br Br CO2H CO2H CO2H O O I II III IV V i. LAH, Et2O ii. H2O i. Mg, Et2O ii. CO2 iii. H3O+ F SOCl2 a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products 56 Section: 17.3 Difficulty Level: Hard 110) What would be the final product, F, of the following sequence of reactions? CO2H i. LAH, Et2O ii. H2O i. Mg, Et2O ii. CO2 iii. H3O+ F PBr3 a) 1-Bromo-2-methyl propane b) 3-Bromo-3-methylbutanoic acid c) Butanoic acid d) 3-Methylbutanoic acid e) Methyl 2-methylproanoate Answer: D Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 111) What would be the final product, F, of the following sequence of reactions? a) 1-Bromo-2-methyl propane b) 3-Bromo-3-methylbutanoic acid c) Butanoic acid d) 3-Methylbutanoic acid e) Methyl 2-methylproanoate Answer: D Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 112) What would be the final product, F, of the following sequence of reactions? 57 Br Br CO2H CO2H CO2H O O I II III IV V i. LAH, Et2O ii. H2O i. Mg, Et2O ii. CO2 iii. H3O+ F PBr3 2-methylpropanoic acid a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 113) What would be the final product, F, of the following sequence of reactions? a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 58 114) What is the reactant of the following reaction sequence? CO2H Br Br CO2H CO2H CO2H O I II III IV V i. LAH, Et2O ii. H2O i. Mg, Et2O ii. CO2 iii. H3O+ PBr ? 3 a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 115) What is the reactant of the following reaction sequence? a) I b) II c) III d) IV e) V Answer: D 59 Topic: Reaction Products Section: 17.3 Difficulty Level: Hard 116) What would be the final organic product of the following reaction? i. LAH, Et2O ii. H2O Br ? i. Mg, Et2O ii. CO2 iii. H3O+ a) 2,2-Dimethylpropanoic acid b) Methyl 2,2-dimethylpropanoate c) 2,2-Dimethyl-1-propanol d) t-Butyl methyl ether e) 3,3-Dimethyl-2-butanone Answer: C Topic: Reaction Products Section: 12.3 and 17.3 Difficulty Level: Hard 117) What would be the final organic product of the following reaction? i. LAH, Et2O ii. H2O ? i. Br2, ROOR ii. Mg, Et2O iii. CO2 vi. H3O+ a) 2,2-Dimethylpropanoic acid b) Methyl 2,2-dimethylpropanoate c) 2,2-Dimethyl-1-propanol d) t-Butyl methyl ether e) 3,3-Dimethyl-2-butanone Answer: C Topic: Reaction Products Section: 12.3 and 17.3 Difficulty Level: Hard 118) What would be the final organic product of the following reaction? 60 C6H5 Cl NaCN i. excess LAH, Et2O ii. H2O ? a) C6H5CH2CH2CO2H b) C6H5CH2CH2NH2 c) C6H5CH2CH(CH3)CN d) C6H5CH2CH=NH e) C6H5CH2NH2 Answer: B Topic: Reaction Products Section: 16.9 and 17.3 Difficulty Level: Hard 119) What would be the final organic product of the following reaction? i. excess LAH, Et2O ii. H2O ? i. Br2, ROOR ii. NaCN a) C6H5CH2CH2CO2H b) C6H5CH2CH2NH2 c) C6H5CH2CH(CH3)CN d) C6H5CH2CH=NH e) C6H5CH2NH2 Answer: B Topic: Reaction Products Section: 16.9 and 17.3 Difficulty Level: Hard 120. What would be the final organic product of the following reaction? i. LAH, Et2O ii. H2O ? i. Br2, ROOR ii. Mg, Et2O iii. CO2 iv. H3O+ a) (CH3)3CCO2H b) (CH3)3CCOCH3 c) (CH3)3CCH2OH d) (CH3)3COCH3 e) (CH3)3CCO2CH3 61 Answer: C Topic: Reaction Products Section: 12.3 and 17.3 Difficulty Level: Hard 121) What is the product of this reaction? O CO2H HO O O I II III O O O O O O O IV V O HO O ? O i. m-CPBA ii. CH3OH, H+ a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.7 Difficulty Level: Hard 122) What is the product of this reaction? 62 O O O III I II O O O O O O O IV V HO O ? i. m-CPBA ii. CH3OH, H+ O COOH HO a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.7 Difficulty Level: Hard 123) What is the product of this reaction? O CO2H HO O O I II III O O O O O O O IV V O HO O ? i. Hg(OAc)2, H2O ii. NaBH4 iii m-CPBA iv. CH3OH, H+ a) I b) II 63 c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.7 Difficulty Level: Hard 124) What final product, Q, would be obtained via the following reaction sequence? H H H3C OH C Cl 6H5 O 6H5 OC O Q + pyridine OH− / H2O heat a) cis-3-Methylcyclopentanol b) trans-3-Methylcyclopentanol c) Equal amounts of a) and b) d) 3-Methylcyclopentanone e) None of these choices. Answer: B Topic: Reaction Products Section: 17.7 Difficulty Level: Hard 125) (R)-3-hexanol is subjected to the following sequence of reactions: i) acetyl chloride, pyridine; ii) NaOH(aq), heat. What is(are) the likely final product(s)? a) (R)-3-hexanol b) (S)-2-hexanol c) Equal amounts of (R)-3-hexanol and (S)-2-hexanol d) 2-Hexene (cis and trans) e) 1-Hexen-2-ol Answer: A Topic: Reaction Products Section: 17.7 Difficulty Level: Hard 64 126) Predict the final product likely to be obtained when (S)-2-methyl-3-pentanol is subjected to the following sequence of reactions: i) benzoyl chloride; ii) NaOH (aq), heat. a) (S)-2-methyl-3-pentanol b) (R)-2-methyl-3-pentanol c) (R,S)-2-methyl-3-pentanol d) 2-Methyl-2-pentene e) (R,S)-2-methyl-3-pentanol and 2-methyl-2-pentene in more or less equal amounts Answer: A Topic: Reaction Products Section: 17.7 Difficulty Level: Hard 127) What would be the final product? C6H5CH2CONH2 i. CH3MgI, Et2O ii. H3O+ P4O10 heat ? a) C6H5CH2CO2CH3 b) C6H5CH2CH2NHCH3 c) C6H5CH2COCH3 d) C6H5CH2CH(CH3)CN e) C6H5CH2CH=NCH3 Answer: C Topic: Reaction Products Section: 17.8 Difficulty Level: Hard 128) What would be the final product? C6H5CH2CONH2 i. CH3Li, Et2O ii. H3O+ P4O10 heat ? a) C6H5CH2CO2CH3 b) C6H5CH2CH2NHCH3 c) C6H5CH2COCH3 d) C6H5CH2CH(CH3)CN e) C6H5CH2CH=NCH3 Answer: C 65 Topic: Reaction Products Section: 17.8 Difficulty Level: Hard 129) What would be the final product? C6H5CH2CONH2 i. DIBAL-H, -78o C ii. H3O+ P4O10 heat ? a) C6H5CH2CO2CH3 b) C6H5CH2CH2NHCH3 c) C6H5CH2COCH3 d) C6H5CH2CH(CH3)CN e) C6H5CH2CHO Answer: E Topic: Reaction Products Section: 17.8 Difficulty Level: Hard 130) What would be the final product? C6H5CH2CONH2 i. PhLi, Et2O ii. H3O+ P4O10 heat ? a) C6H5CH2CO2Ph b) C6H5CH2CH2NHPh c) C6H5CH2COPh d) C6H5CH2CH(Ph)CN e) C6H5CH2CH=NPh Answer: C Topic: Reaction Products Section: 17.8 Difficulty Level: Hard 131) What would be the final product of this reaction sequence? 66 I II V CN III NH2 O H N H N O NH2 IV CO2 NH4 i. Cl2, FeCl3 ii. Mg. ether iii. PCl3 iv. NH3 v. P4O10 ? a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 17.5 and 17.8 Difficulty Level: Hard 132) What would be the final product of this reaction sequence? 67 I II III V CN NH2 O H N H N O NH2 IV COCH3 i. Br2, FeBr3 ii. Mg, ether iii. PCl3 iv. NH3 v. P4O10 vi. CH3Li, ether vii. H3O+ ? a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 16.5, 17.5 and 17.8 Difficulty Level: Hard 133) What would be the final product of this reaction sequence? a) Benzonitrile b) Benzamide c) Aniline d) Acetophenone e) Acetanilide 68 Answer: D Topic: Reaction Products Section: 16.5, 17.5 and 17.8 Difficulty Level: Hard 134) What is the final product of this sequence of reactions? I II I IV V O O NH2 II CN NH2 NHCl O NH2 O i. SOCl2 ii. excess NH3 ? i. Br2, light ii. Mg, Et2O iii. CO2 iv. H3O+ a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 17.3, 17.5 and 17.8 Difficulty Level: Hard 135) What is the final product of this sequence of reactions? 69 I II I IV V O O NH2 II CN NH2 NHCl O NH2 O ? i. Br2, light ii. Mg, Et2O iii. CO2 iv. H3O+ DCC NH3 a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 17.3, 17.5 and 17.8 Difficulty Level: Hard 136) What is the final product of this sequence of reactions? I II I IV V O O NHCH3 II CN NHCH3 NHBr O NHCH3 O ? i. Br2, light ii. Mg, Et2O iii. CO2 iv. H3O+ DCC CH3NH2 a) I 70 b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 17.3, 17.5 and 17.8 Difficulty Level: Hard 137) What is the final product of this sequence of reactions? a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.3, 17.5 and 17.8 Difficulty Level: Hard 138) What is the final product of this sequence of reactions? 71 a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.3, 17.5 and 17.8 Difficulty Level: Hard 139) What is the final product of this sequence of reactions? a) I 72 b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 17.3, 17.5 and 17.8 Difficulty Level: Hard 140) N,N-Dimethylbenzamide can be made from which of the following? a) O C6H5 O N H + b) O C Cl 6H5 N H + c) O C6H5 O C6H5 O N H + d) O C6H5 NH2 + CH3MgCl e) More than one of these choices. Answer: E Topic: Synthesis Section: 17.8 Difficulty Level: Medium 141) N,N-Dimethylbenzamide can be made from which of the following? a) O C6H5 O N H + b) O C Cl 6H5 N H + c) N + H DCC C6H5COOH d) O C6H5 NH2 + CH3MgCl e) More than one of these choices. 73 Answer: E Topic: Synthesis Section: 17.8 Difficulty Level: Medium 142) Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid? a) Br i. Mg, Et2O ii. CO2 iii. H3O+ b) i. KMnO4, OH− , heat ii. H3O+ OH c) Br i. CN− ii. OH− , H2O, heat iii. H3O+ d) All of these choices. e) Only two of these choices. Answer: E Topic: Synthesis Section: 17.3 Difficulty Level: Medium 143) Choose the reagent(s) that would bring about the following reaction: CH3CH2CH2COCl ⎯⎯⎯→ CH3CH2CH2CHO a) H2/Ni b) Li/liq NH3 c) LiAl(OC(CH3)3)3H d) NaBH4, CH3OH e) LiAlH4, ether Answer: C Topic: Synthesis Section: 16.4 and 17.5 Difficulty Level: Medium 74 144) Choose the reagent(s) that would bring about the following reaction: CH3CH2CH2COCl ⎯⎯⎯→ CH3CH2CH2CHO a) H2/Ni b) DIBAL-H c) LiAl(OC(CH3)3)3H d) NaBH4, CH3OH e) LiAlH4, ether Answer: C Topic: Synthesis Section: 16.4 and 17.5 Difficulty Level: Medium 145) Which of the following compounds is capable of forming a δ-lactone? a) 5-Hydroxypentanoic acid b) Pentanedioic acid c) 4-Hydroxypentanoic acid d) 3-Hydroxypentanoic acid e) 2-Hydroxypentanoic acid Answer: A Topic: Synthesis Section: 17.7 Difficulty Level: Medium 146) Which of the following reactions could be used to synthesize ethyl acetate? a) CH3CH2OH + (CH3CO)2O + pyridine ⎯⎯⎯→ b) CH3CH2OH + (CH3CO)2O ⎯⎯⎯→ c) CH3CH2OH + CH3CO2H + H3O+ ⎯⎯⎯→ d) Two of these choices. e) All of these choices. Answer: E Topic: Synthesis Section: 17.7 Difficulty Level: Medium 75 147) Choose the reagent(s) that would bring about the following reaction: CH3CH2CH2CO2CH3 ⎯⎯⎯→ CH3CH2CH2CHO a) H2/Ni b) Li/liq NH3 c) Al(CH2CH(CH3)2)2H d) NaBH4, CH3OH e) LiAlH4, ether Answer: C Topic: Synthesis Section: 16.4 and 17.7 Difficulty Level: Medium 148) Which of the following reactions would constitute a reasonable synthesis of propyl acetate? a) OH OH O HA + b) OH Cl O + pyridine c) OH O O + O d) All of these choices. e) None of these choices. Answer: D Topic: Synthesis Section: 17.6 and 17.7 Difficulty Level: Medium 149) Which of the following would serve as a reasonable synthesis of ethyl benzoate? a) O C6H5 OH + OH HA reflux excess b) O C Cl 6H5 + OH base c) O C6H5 O C6H5 O + OH 76 d) All of these choices. e) None of these choices. Answer: D Topic: Synthesis Section: 17.7 Difficulty Level: Medium 150) Which of the following combinations of reagents would not produce an ester? a) O H3C ONa + Br b) O H3C ONa + OH c) HA O H3C OH + OH d) O H3C O CH3 O OH + e) + O H Cl 3C OH Answer: B Topic: Synthesis Section: 17.7 Difficulty Level: Medium 151) Choose the reagent(s) that would bring about the following reaction: CH3CH2CH2COOH ⎯⎯⎯→ CH3CH2CH2CH2OH a) H2/Ni b) Li/liq NH3 c) LiAlH[OC(CH3)3]3 d) NaBH4, CH3OH e) LiAlH4, ether Answer: E Topic: Synthesis Sections: 12.3 and 17.13 77 Difficulty Level: Medium 152) Choose the reagent(s) that would bring about the following reaction: CH3C≡CCH2CO2CH2CH3 ⎯⎯⎯→ CH3C≡CCH2CH2OH a) H2/Ni b) Li/liq NH3 c) LiAlH[OC(CH3)3]3 d) NaBH4, CH3OH e) LiAlH4, ether Answer: E Topic: Synthesis Sections: 12.3 and 17.13 Difficulty Level: Medium 153) Which of the reactions listed below would serve as a synthesis of acetophenone, C6H5COCH3 ? a) (CH3CO)2O + C6H6 AlCl3 b) H3C Cl O AlCl3 + C6H6 c) C6H5 OCH3 O + CH3MgI d) Two of these choices. e) All of these choices. Answer: D Topic: Synthesis Sections: 15.7, 15.9, and 17.13 Difficulty Level: Medium 154) Which of the following would serve as syntheses of (CH3)3CCO2H? a) i. Cl2/OH− (excess) ii. H3O+ O 78 b) Br i. CN− ii. H3O+ (heat) c) Br i. Mg, Et2O ii. CO2 iii. H3O+ d) i. Cl2/OH− (excess) ii. H3O+ O and Br i. CN− ii. H3O+ (heat) e) i. Cl2/OH− (excess) ii. H3O+ O and Br i. Mg, Et2O ii. CO2 iii. H3O+ Answer: E Topic: Synthesis Section: 17.3 Difficulty Level: Medium 155) Which carboxylic acid would decarboxylate when heated to 100-150°C? HO2C CO2H I CO2H O II HO2C CO2H III a) I b) II c) III d) More than one of these choices e) None of these choices. Answer: D Topic: Synthesis Section: 17.10 Difficulty Level: Medium 156) Which reactant is unlikely to produce the indicated product upon strong heating? a) 2,2-Dimethylpropanedioic acid Æ 2-methylpropanoic acid b) 2-Ethylpropanedioic acid Æ Butanoic acid c) 2-Methyl-3-oxo-pentanoic acid Æ 3-Pentanone d) 2-Methyl-4-oxo-pentanoic acid Æ 2-Methyl-3-butanone 79 e) 4-Methyl-3-oxo-heptanoic acid Æ 3-Methyl-2-hexanone Answer: D Topic: Synthesis Section: 17.10 Difficulty Level: Hard 157) Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid? a) i. Br2, ROOR ii. Mg, Et2O iii. CO2 iv. H3O+ isobutane b) i. KMnO4, OH− , heat ii. H3O+ OH c) i. Br2, ROOR ii. CN− iii. OH−, H2O, heat iv. H3O+ isobutane d) All of these choices. e) Only two of these choices. Answer: E Topic: Synthesis Section: 17.3 Difficulty Level: Hard 158) Which of the following would serve as syntheses of (CH3)3CCO2H? a) i. Cl2/OH− (excess) ii. H3O+ 3,3-dimethylbutan-2-one b) i. Br2, ROOR ii. CN− iii. OH−, H2O, heat iv. H3O+ isobutane 80 c) i. Br2, ROOR ii. Mg, Et2O iii. CO2 iv. H3O+ isobutane d) i. Cl2/OH− (excess) ii. H3O+ 3,3-dimethylbutan-2-one and i. Br2, ROOR ii. CN− iii. OH−, H2O, heat iv. H3O+ isobutane e) i. Cl2/OH− (excess) ii. H3O+ 3,3-dimethylbutan-2-one and i. Br2, ROOR ii. Mg, Et2O iii. CO2 iv. H3O+ isobutane Answer: E Topic: Synthesis Section: 17.3 Difficulty Level: Hard 159) Which of the following would serve as syntheses of (CH3)3CCO2H? a) i. Cl2/OH− (excess) ii. H3O+ O b) i. Br2, ROOR ii. CN− iii. OH−, H2O, heat iv. H3O+ c) i. Br2, ROOR ii. Mg, Et2O iii. CO2 iv. H3O+ d) i. Cl2/OH− (excess) ii. H3O+ O and i. Br2, ROOR ii. CN− iii. OH−, H2O, heat iv. H3O+ 81 i. Br2, ROOR ii. Mg, Et2O iii. CO2 iv. H3O+ e) i. Cl2/OH− (excess) ii. H3O+ O and Answer: E Topic: Synthesis ficulty Level: Hard would yield (S)-2-butanol? ) Section: 17.3 Dif 160) Which of the following i. CH3CO2 − Na+ ii. OH− , H2O, heat (R)-2-Bromobutane a OH− , H2O, heat (R)-2-Bromobutane b) OH− , H2O, heat (S)-sec-Butyl acetate c) d) All of these choices. one of these choices. wer: D he reactions listed be [Show Less]