Package Title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 15 Question Type: Multiple Choice 1) Which of these is the rate-determining
... [Show More] step in the nitration of benzene? a) Protonation of nitric acid by sulfuric acid b) Protonation of sulfuric acid by nitric acid c) Loss of a water molecule by the protonated species to produce the nitronium ion d) Addition of the nitronium to benzene to produce the arenium ion e) Loss of a proton by the arenium ion to form nitrobenzene Answer: D Topic: Mechanisms and Intermediates Section: 15.2 Difficulty Level: Medium 2) Which of these is the rate-determining step in the sulfonation of benzene? a) Formation of SO3 from sulfuric acid b) Protonation of SO3 sulfuric acid c) Addition of SO3H + to benzene to form the arenium ion d) Loss of a proton from the arenium ion to form benzenesulfonic acid e) None of these choices. Answer: C Topic: Mechanisms and Intermediates Section: 15.2 Difficulty Level: Medium 3) Which of these is the rate-determining step in the bromination of benzene? a) Complexation of bromine with the iron(III) bromide catalyst b) Formation of Br+ ion c) Addition of Br+ to benzene to form the arenium ion d) Loss of a proton from the arenium ion to form bromobenzene e) None of these choices. 1 Contact: [email protected] Answer: C Topic: Mechanisms and Intermediates Section: 15.2 Difficulty Level: Medium 4) Which of the following structures contribute(s) to the resonance hybrid of the intermediate formed when bromobenzene undergoes para-chlorination? Br H Cl Br H Cl Br H Cl Br H Cl I II III IV + + + .. .. .. .. : : : + : : : : a) I b) II c) III d) IV e) All of these choices. Answer: E Topic: Mechanisms and Intermediates Section: 15.11 Difficulty Level: Medium 5) Which of the following structures contribute(s) to the resonance hybrid of the intermediate formed when chlorobenzene undergoes para-chlorination? Cl H Cl Cl H Cl Cl H Cl Cl H Cl I II III IV + + + .. .. .. .. : : : + : : : : a) I b) II c) III d) IV e) All of these choices. Answer: E Topic: Mechanisms and Intermediates 2 Section: 15.11 Difficulty Level: Medium 6) Which of the following structures contribute(s) to the resonance hybrid of the intermediate formed when acetanilide undergoes para-bromination? NHCOCH3 H Br NCOCH3 H Br NHCOCH3 H Br NHCOCH3 H Br I II III IV + + + : : : + a) I b) II c) III d) IV e) All of these choices. Answer: E Topic: Mechanisms and Intermediates Section: 15.11 Difficulty Level: Medium 7) Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable? NH2 H Cl NH2 H Cl NH2 H Cl NH2 H Cl I II III IV + + + : + : : a) I b) II c) III d) IV e) None of these choices. Answer: B Topic: Mechanisms and Intermediates Section: 15.11 Difficulty Level: Medium 3 8) Consider the structures given below. Which of them would be a relatively stable contributor to the hybrid formed when toluene undergoes para bromination? a) I b) II c) III d) IV e) V Answer: C Topic: Mechanisms and Intermediates Section: 15.11 Difficulty Level: Medium 9) Which of the following structures does not contribute to the resonance hybrid of the intermediate formed when nitrobenzene undergoes meta-chlorination? N N N I II III O O O O O O Cl H Cl H Cl H + + + : : : : : : : : : .. .. .. .. .. .. a) I b) II c) III d) None of these contribute. e) All of these contribute. Answer: E Topic: Mechanisms and Intermediates Section: 15.11 Difficulty Level: Medium 10) Consider the resonance forms shown for the arenium ionformed from the bromination of acetanilide. Which resonance form contributes most to the overall resonance hybrid? 4 a) I b) II c) III d) IV e) All contribute equally. Answer: C Topic: Mechanisms and Intermediates Section: 15.11 Difficulty Level: Medium 11) Consider the resonance forms shown for the arenium ionformed from the bromination of acetanilide. Which resonance form contributes most to the overall resonance hybrid? a) I b) II c) III d) IV e) All contribute equally. Answer: D 5 Topic: Mechanisms and Intermediates Section: 15.11 Difficulty Level: Medium 12) The electrophilic bromination or chlorination of benzene requires, in addition to the halogen: a) a hydroxide ion. b) a Lewis base. c) a Lewis acid. d) peroxide. e) ultraviolet light. Answer: C Topic: Other EAS Considerations Section: 15.3 Difficulty Level: Easy 13) In electrophilic aromatic substitution, the attacking species (the electrophile) necessarily is a: a) neutral species. b) positively charged species. c) lewis acid. d) proton. e) carbocation. Answer: C Topic: Other EAS Considerations Section: 15.2 Difficulty Level: Medium 14) Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction? a) Chlorobenzene b) Nitrobenzene c) Acetophenone d) (Trifluoromethyl) benzene e) All of these choices could be used. Answer: A 6 Topic: Other EAS Considerations Section: 15.8 Difficulty Level: Medium 15) Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the case of: a) Friedel-Crafts alkylation b) Friedel-Crafts acylation c) Nitration d) Sulfonation e) Chlorination Answer: A Topic: Other EAS Considerations Section: 15.8 Difficulty Level: Medium 16) This substituent deactivates the benzene ring towards electrophilic substitution but directs the incoming group chiefly to the ortho and para positions. a) -OCH2CH3 b) -NO2 c) -F d) -CF3 e) -NHCOCH3 Answer: C Topic: Other EAS Considerations Section: 15.10 and 15.11 Difficulty Level: Medium 17) This molecule does not normally participate as a reactant in a Friedel-Crafts reaction. a) Benzene b) Chlorobenzene c) Nitrobenzene d) Toluene e) tert-Butylbenzene Answer: C 7 Topic: Other EAS Considerations Section: 15.8 Difficulty Level: Medium 18) Which one of these molecules can be a reactant in a Friedel-Crafts reaction? a) Aniline b) Nitrobenzene c) Chloroethene d) Bromobenzene e) p-Bromonitrobenzene Answer: D Topic: Other EAS Considerations Section: 15.8 Difficulty Level: Medium 19) Which one of these molecules can be a reactant in a Friedel-Crafts reaction? a) Aniline b) Benzenesulfonic acid c) Chloroethene d) Bromobenzene e) p-Bromonitrobenzene Answer: D Topic: Other EAS Considerations Section: 15.8 Difficulty Level: Medium 20) Which reagent would you use as the basis for a simple chemical test that would distinguish between toluene and vinylbenzene (C6H5CH=CH2)? a) NaOH/H2O b) Br2/CCl4 c) NaBH4 d) HCl/H2O e) NaI in acetone Answer: B 8 Topic: Functional Group Tests Sections: 14.2, 14.3 and 15.3 Difficulty Level: Medium 21) Which reagent or test could you use to distinguish between phenylacetylene and vinylbenzene? a) NaOH/H2O b) Br2/CCl4 c) IR Spectroscopy d) CrO3/H2SO4 e) Concd. H2SO4 Answer: C Topic: Nomenclature, Functional Group Tests Section: 14.2, 14.11 and 15.3 Difficulty Level: Medium 22) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF? a) butylbenzene b) 2-phenylbutane c) 2-methyl-1-phenylpropane d) t-butylbenzene e) 2,2-diphenylbutane Answer: B Topic: Nomenclature, Reaction Products Section: 14.2 and 15.6 Difficulty Level: Hard 23) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl3? a) butylbenzene b) 2-phenylbutane c) 2-methyl-1-phenylpropane d) t-butylbenzene e) 2,2-diphenylbutane 9 Answer: B Topic: Nomenclature, Reaction Products Section: 14.2 and 15.6 Difficulty Level: Hard 24) A mixture of chlorobenzene (1 mol) and acetanilide (1mol) is allowed to react with Br2 (0.5 mol) in the presence of trace amounts of FeBr3. What is the principal product of the competing reactions? a) 1-bromo-4-chlorobenzene b) 1-bromo-2-chlorobenzene c) 1-bromo-3-chlorobenzene d) 4-bromoacetanilide e) 3-bromoacetanilide Answer: D Topic: Nomenclature, Reaction Products Section: 14.2, 15.3, and 15.8 Difficulty Level: Hard 25) A mixture of chlorobenzene (1 mol) and anisole (1mol) is allowed to react with Br2 (0.5 mol) in the presence of trace amounts of FeBr3. What is the principal product of the competing reactions? a) 1-bromo-4-chlorobenzene b) 1-bromo-2-chlorobenzene c) 1-bromo-3-chlorobenzene d) 4-bromoanisole e) 3-bromoanisole Answer: D Topic: Nomenclature, Reaction Products Section: 14.2, 15.3, and 15.8 Difficulty Level: Hard 26) Which of the following reactions could be used to synthesize tert-butylbenzene? a) H 2 S O 4 C 6 H 6 + C H 2 = C ( C H 3 ) 2 10 b) H 2 S O 4 C 6 H 6 + ( C H 3 ) 3 C O H c) A l C l 3 C 6 H 6 + ( C H 3 ) 3 C C l d) All of these choices. e) None of these choices. Answer: D Topic: Synthesis Section: 15.6 Difficulty Level: Easy 27) Which of the following reactions could be used to synthesize tert-butylbenzene? a) H 2 S O 4 C 6 H 6 + C H 2 = C ( C H 3 ) 2 b) c) A l C l 3 C 6 H 6 + ( C H 3 ) 3 C C l d) All of these choices. e) None of these choices. Answer: D Topic: Synthesis Section: 15.6 Difficulty Level: Easy 28) Which of the following reactions could be used to synthesize tert-butylbenzene? a) b) c) A l C l 3 C 6 H 6 + ( C H 3 ) 3 C C l d) All of these choices. e) None of these choices. Answer: D 11 Topic: Synthesis Section: 15.6 Difficulty Level: Easy 29) Consider the following reaction: what is the expected product? IV II V III Cl Br Br Cl NH2 NH2 Cl Br NH2 Cl Br I Br H2N Cl NH2 Br Br Br Br NH2 Cl Br2 , H2O ? a) I b) II c) III d) IV e) V Answer: B Topic: Synthesis Section: 15.3 Difficulty Level: Easy 30) Which of the following reactions would yield isopropylbenzene as the major product? b) B e n z e n e H 2 S O 4 C H 3 C H C H 3 O H c) B e n z e n e A l C l 3 C H 3 C H C H 3 C l 12 d) B e n z e n e A l C l 3 C H 3 C H 2 C H 2 C l e) All of these choices. Answer: E Topic: Synthesis Section: 15.6 Difficulty Level: Medium 31) Which of the following reactions would yield isopropylbenzene as the major product? a) b) B e n z e n e H 2 S O 4 C H 3 C H C H 3 O H c) B e n z e n e A l C l 3 C H 3 C H C H 3 C l d) B e n z e n e A l C l 3 C H 3 C H 2 C H 2 C l e) All of these choices. Answer: E Topic: Synthesis Section: 15.6 Difficulty Level: Medium 32) Which of the following reactions would yield isopropylbenzene as the major product? a) 13 b) c) B e n z e n e A l C l 3 C H 3 C H C H 3 C l d) B e n z e n e A l C l 3 C H 3 C H 2 C H 2 C l e) All of these choices. Answer: E Topic: Synthesis Section: 15.6 Difficulty Level: Medium 33) Which of the following reactions would produce isopropylbenzene? a) Cl AlCl3 Benzene b) Benzene HF c) OH H2SO4 Benzene d) Br AlCl3 Benzene e) All of these choices. Answer: E Topic: Synthesis Section: 15.6 Difficulty Level: Medium 34) Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane? 14 a) C6H5CH2CH3 + Cl2, Fe b) C6H5CH2CH3 + Cl2, 400C c) C6H5CH2CH2OH + SOCl2 d) C6H5CH=CH2 + HCl, peroxide e) C6H6 + CH3CH2Cl, AlCl3 Answer: C Topic: Synthesis Sections: 11.9 and 15.6 Difficulty Level: Medium 35) Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane? a) C6H5CH2CH3 + Cl2, Fe b) C6H5CH2CH3 + Cl2, 400C c) C6H5CH2CH2OH + PCl5 d) C6H5CH=CH2 + HCl, peroxide e) C6H6 + CH3CH2Cl, AlCl3 Answer: C Topic: Synthesis Sections: 11.9 and 15.6 Difficulty Level: Medium 36) Which of the following reactions would produce cumene? a) Cl AlCl3 Benzene b) Benzene HF c) OH H2SO4 Benzene d) Br AlCl3 Benzene e) All of these choices. 15 Answer: E Topic: Synthesis Section: 15.6 Difficulty Level: Hard 37) Which of the following reactions would yield cumene as the major product? a) B e n z e n e H 2 S O 4 C H 3 C H C H 2 b) B e n z e n e H 2 S O 4 C H 3 C H C H 3 O H c) B e n z e n e A l C l 3 C H 3 C H C H 3 C l d) B e n z e n e A l C l 3 C H 3 C H 2 C H 2 C l e) All of these choices. Answer: E Topic: Synthesis Section: 15.6 Difficulty Level: Hard 38) Which of the following reactions would give the product(s) indicated in substantial amounts (i.e., in greater than 50% yield)? 16 + C H 3 C l N H 2 A l C l 3 N H 2 N H 2 a n d C H 3 C H 3 N H 2 N H 2 + C H 3 C l A l C l 3 C H 3 + C H 3 C H 2 C H 2 C l A l C l 3 C H 2 C H 2 C H 3 I I I I I I a) I b) II c) III d) All of these choices. e) None of these choices. Answer: E Topic: Reaction Products Section: 15.6 and 15.8 Difficulty Level: Easy 39) What would you expect to be the major product obtained from the following reaction? HN O I IV II V HN O HN O HN O HN O III HN O ? AlCl3 excess CH3Cl a) I b) II 17 c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.6 and 15.8 Difficulty Level: Medium 40) What would you expect to be the major product obtained from the following reaction? I IV II V III ? AlCl3 + Cl O O2N O2N O2N O2N O2N O2N O O O O O a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 15.7 and 15.8 Difficulty Level: Medium 41) The major product(s) of the following reaction, 18 O I IV II V O O O O III O ? AlCl3 + Cl O O O O O O would be: a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.7 and 15.8 Difficulty Level: Medium 42) What might be predicted to happen when the following substance undergoes Friedel-Crafts acylation? O2N CH2 A B a) Substitution occurs in ring B, p- to the methylene group. b) Substitution occurs in ring A, o- to the nitro group. c) Substitution occurs in ring A, o- to the methylene group. d) Substitution occurs in ring B, m- to the methylene group. e) None of these choices. No reaction will occur. Answer: A Topic: Reaction Products 19 Section: 15.7 and 15.8 Difficulty Level: Medium 43) What would be the product of the following reaction sequence? IV OH O I II V III OH O O OH i) SOCl2 ii) C6H6 , AlCl3 iii) Zn(Hg), HCl, heat ? a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 44) What would be the product of the following reaction sequence? 20 a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 45) What would be the product of the following reaction sequence? IV OH O I II V III OH O O OH i) PCl5 ii) C6H6 , AlCl3 iii) Zn(Hg), HCl, heat ? a) I 21 b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 46) What would be the product of the following reaction sequence? a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 47) What would be the product of the following reaction sequence? 22 IV OH O I II V III OH O O OH i) SOCl2 ii) C6H6 , AlCl3 iii) Zn(Hg), HCl, heat ? a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 48) What would be the product of the following reaction sequence? 23 a) I b) II c) III d) IV e) V Answer: B Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 49) Which would be the product of the following reaction sequence? IV OH O I II O SO2 CO2 V CH2 III ? i) SOCl2 ii) benzene, AlCl3 iii) Zn(Hg), HCl 24 a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 50) Which would be the product of the following reaction sequence? a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 51) Which would be the product of the following reaction sequence? 25 IV OH O I II O SO2 CO2 V CH2 III ? i) PCl5 ii) benzene, AlCl3 iii) Zn(Hg), HCl a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 52) Which would be the product of the following reaction sequence? a) I b) II c) III d) IV 26 e) V Answer: C Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 53) Which would be the product, X, of the following reaction sequence? IV I II O SO2 CO2 V CH2 III i) benzene, AlCl3 ii) Zn(Hg), HCl X + OH O Ph Ph O O O a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 54) Which would be the product, X, of the following reaction sequence? 27 a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.7 and 15.9 Difficulty Level: Medium 55) The major product(s), D, of the following reaction, 28 C O C H 2 C O C H 2 C O C H 2 C O C H 2 C O C H 2 B r B r B r B r B r 2 F e B r 3 D I I I I I I I V would be: a) I b) II c) III d) IV e) Approximately equal amounts of I and II. Answer: D Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 56) The major product, D, of the following reaction, 29 would be: a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 57) What would you expect to be the major product obtained from the following reaction? 30 C O O H S O 3 H C O O H S O 3 H C O O H S O 3 H C O O H S O 3 H C O O H S O 3 H B r B r B r B r I I I I I I I V B r 2 F e B r 3 ? a) I b) II c) III d) IV e) Equal amounts of II and IV. Answer: C Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 58) What would you expect to be the major product obtained from the following reaction? N O 2 S O 3 H N O 2 S O 3 H N O 2 S O 3 H N O 2 S O 3 H N O 2 S O 3 H B r B r B r B r I I I I I I I V B r 2 F e B r 3 ? a) I b) II c) III d) IV e) Equal amounts of II and IV. Answer: C Topic: Reaction Products Section: 15.3 and 15.10 31 Difficulty Level: Medium 59) What would you expect to be the major product obtained from the following reaction? O O I IV II V O O Br O O Br O O Br O O Br III O O Br ? Br2 , FeBr3 a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 60) What would you expect to be the major product obtained from the following reaction? 32 I IV II V III ? 1 equiv. Br2 FeBr3 Br Br Br Br Br a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 61) What would you expect to be the major product obtained from the following reaction? 33 I IV II V III ? 1 equiv. Cl2 FeCl3 Cl Cl Cl Cl Cl a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 62) What would you expect to be the major product obtained from the following reaction? HN O I IV II V HN O Cl HN O Cl HN O Cl HN O Cl III HN O Cl ? Cl2 , FeCl3 34 a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 63) What would you expect to be the major product obtained from the following reaction? O I IV II V O Br O Br O Br O III O ? Br 1 equivalent Br2 Br FeBr3 a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 35 64) What would you expect to be the major product obtained from the monobromination of mdichlorobenzene? I II III Cl Cl Br Cl Cl Br Cl Br Cl a) I b) II c) III d) Equal amounts of I and II. e) Equal amounts of I, II and III. Answer: B Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 65) Which would be the major product(s) of the following reaction? H3CO O I Br2 , FeBr3 II H3CO O Br Br H3CO O Br2Fe H3CO O III ? a) I b) II c) III d) I and II in roughly equal amounts. e) I and III in roughly equal amounts. Answer: A Topic: Reaction Products Section: 15.3 and 15.10 Difficulty Level: Medium 36 66) What would you expect to be the major product obtained from the following reaction? HN O I IV II V HN O O2N HN O O2N HN O NO2 HN O NO2 III HN O NO2 ? HNO3 H2SO4 , heat a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 67) What would you expect to be the major product obtained from the following reaction? 37 O O I IV II V O O O2N O O O2N O O NO2 O O NO2 III O O NO2 ? HNO3 H2SO4 , heat a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 68) What would be the major product(s) of the following reaction? CO2H NO2 I II III CO2H NO2 NO2 CO2H NO2 NO2 CO2H O2N NO2 O2N CO2H NO2 IV HNO3 H2SO4 , heat ? a) I b) II c) III 38 d) IV e) Approximately equal amounts of II and IV. Answer: C Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 69) What would you expect to be the major product obtained from the following reaction? I IV II V III O2N NO2 NO2 O2N NO2 ? 1 equiv. HNO3 H2SO4 , heat a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 70) What would you expect to be the major product obtained from the following reaction? 39 HN I IV II V HN O2N HN O2N HN NO2 HN NO2 III HN ? HNO3 H2SO4 , heat NO2 a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 71) What would you expect to be the major product(s) obtained from the mononitration of mdichlorobenzene? I II III Cl Cl NO2 Cl Cl NO2 Cl O Cl 2N a) I b) II c) III d) Equal amounts of I and II. e) Equal amounts of I, II and III. Answer: B 40 Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 72) What would you expect to be the major product(s) obtained from the following reaction? I II III IV SO3H NO2 HO O SO3H NO2 HO O O2N SO3H HO O O2N SO3H HO O SO3H HO O HNO3 H2SO4 , heat ? a) I b) II c) III d) IV e) Equal amounts of I and II. Answer: C Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 73) The major product(s), D, of the following reaction 41 O O O O O O 2 N N O 2 N O 2 N O 2 H N O 3 H 2 S O 4 D I I I I I I I V would be: a) I b) II c) III d) IV e) Equal amounts of I and II. Answer: D Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 74) Which would be the major product(s) of the following reaction? HO O I HNO3 H2SO4 II HO O NO2 NO2 HO O HO3S HO O III ? a) I b) II c) III d) I and II in roughly equal amounts. 42 e) I and III in roughly equal amounts. Answer: A Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 75) Which would be the major product(s) of the following reaction? H3CO O I HNO3 H2SO4 II H3CO O NO2 NO2 H3CO O HO3S H3CO O III ? a) I b) II c) III d) I and II in roughly equal amounts. e) I and III in roughly equal amounts. Answer: A Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Medium 76) What would be the major product(s) of the following reaction? 43 NO2 O I II III NO2 SO3H O NO2 SO3H O HO3S NO2 O HO3S NO2 O IV ? H2SO4 a) I b) II c) III d) Equal amounts of I and IV. e) Equal amounts of II and IV. Answer: C Topic: Reaction Products Section: 15.5 and 15.10 Difficulty Level: Medium 77) What would be the major product(s) of the following reaction? NO2 O I II III NO2 SO3H O NO2 SO3H O HO3S NO2 O HO3S NO2 O IV ? H2SO4 SO3 a) I b) II c) III d) Equal amounts of I and IV. e) Equal amounts of II and IV. Answer: C 44 Topic: Reaction Products Section: 15.5 and 15.10 Difficulty Level: Medium 78) The major product(s), C, of the following reaction, C l C l S O 3 H 2 S O 4 C C l C l C l C l C l C l S O 3 H S O 3 H H O 3 S I I I I I I would be: a) I b) II c) III d) Approximately equal amounts of I and II. e) Approximately equal amounts of I and III. Answer: B Topic: Reaction Products Section: 15.5 and 15.10 Difficulty Level: Medium 79) The major product(s), A, of the following reaction, C H 3 C H 2 C l 2 , h 4 0 0 - 6 0 0 o C C H 3 C H 2 C l C H 3 C H 2 C l C H 2 C H 2 C H 3 C H C l C l I I I I I I I V A would be: 45 a) I b) II c) A mixture of I and II. d) III e) IV Answer: E Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 80) The major product(s) of the following reaction, excess Cl2 400 o - 600 oC ? Cl Cl Cl Cl Cl Cl Cl Cl I II III IV a) I b) II c) A mixture of I and II. d) III e) IV Answer: A Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 81) The major product(s) of the following reaction, 46 ? Br Br Br Br Br Br Br Br I II III IV excess NBS ROOR a) I b) II c) A mixture of I and II. d) III e) IV Answer: D Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 82) The major product(s), A, of the following reaction, ? Br Br I II III IV ROOR Br Br NBS would be: a) I b) II c) A mixture of I and II. 47 d) III e) IV Answer: E Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 83) What would be the major product of the following reaction? C H 2 C H 2 C H 3 C H 2 C H 2 C H 3 C H 2 C H 2 C H 3 C H C H 2 C H 3 C H 2 C H C H 3 C H 2 C H 2 C H 2 C l C l C l C l C l C l 2 4 0 0 o C ? I I I I I I I V V a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 84) What would be the major product of the following reaction? 48 ? Br Br I II III IV ROOR Br Br NBS Br V a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 85) What would be the major product of the following reaction? ? Br Br Br Br Br Br Br Br I II III IV excess NBS ROOR Br Br IV 49 a) I b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 86) What would you expect to be the major product obtained from the following reaction? I IV II V III ? Cl2 Cl Cl Cl Cl Cl peroxides a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 87) What would you expect to be the major product obtained from the following reaction? 50 I IV II V III ? Cl2 Cl Cl Cl Cl Cl light a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 88) What would be the major product of the following reaction? I IV II V Br Br Br Br III Br ? NBS, ROOR light a) I 51 b) II c) III d) IV e) V Answer: C Topic: Reaction Products Section: 15.12 Difficulty Level: Medium 89) When toluene is reacted in turn with 1) Cl2 (large excess), heat, and light and 2) Br2,FeBr3, the chief product is: I Br Cl II CCl3 Br III CCl3 Br IV Br CCl3 a) I b) II c) III d) IV e) A mixture of III and IV. Answer: B Topic: Reaction Products Section: 15.3 and 15.12 Difficulty Level: Medium 90) What would you expect to be the major product obtained from the following reaction? 52 N N I IV II V N N O2N N N O2N N N NO2 N N NO2 III N N NO2 ? HNO3 H2SO4 , heat O O O O O O a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Hard 91) What would you expect to be the major product obtained from the following reaction? 53 a) I b) II c) III d) IV e) A mixture of II and III. Answer: E Topic: Reaction Products Section: 15.4 and 15.10 Difficulty Level: Hard 92) The reaction of benzene with (CH3)3CCH2Cl in the presence of anhydrous aluminum chloride produces principally which of these? 54 IV V I II III a) I b) II c) III d) IV e) V Answer: E Topic: Reaction Products Section: 15.6 and 15.8 Difficulty Level: Hard 93) The reaction of benzene with Cl in the presence of anhydrous aluminum chloride produces principally which of these? I II III IV V a) I b) II 55 c) III d) IV e) V Answer: D Topic: Reaction Products Section: 15.6 and 15.8 Difficulty Level: Hard 94) The reaction of benzene with in the presence of anhydrous aluminum chloride produces principally which of these? a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 15.6 and 15.8 Difficulty Level: Hard 56 95) The reaction of benzene with Cl in the presence of anhydrous aluminum chloride produces principally which of these? I II III IV V a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 15.6 and 15.8 Difficulty Level: Hard 96) The reaction of benzene with in the presence of anhydrous aluminum chloride produces principally which of these? 57 a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 15.6 and 15.8 Difficulty Level: Hard 97) Toluene is subjected to the action of the following reagents in the order given: (1) KMnO4,OH- , heat; then H3O + (2) HNO3, H2SO4 (3) Br2, FeBr3 What is the final product of this sequence? 58 I II III CO2H Br NO2 CO2H Br NO2 CO2H NO2 Br IV V NO2 Br CO2H B NO2 r CH3 a) I b) II c) III d) IV e) V Answer: A Topic: Reaction Products Section: 15.3, 15.4, 15.10, and 15.13 Difficulty Level: Hard 98) Toluene is subjected to the action of the following reagents in the order given: (1) KMnO4,OH- , heat; then H3O + (2) HNO3, H2SO4 (3) Cl2, FeCl3 What is the final product of this sequence? a) I b) II c) III d) IV 59 e) V Answer: D Topic: Reaction Products Section: 15.3, 15.4, 15.10, and 15.13 Difficulty Level: Hard 99) What product would result from the following series of reactions, ? i) AlCl3 ii) N-Bromosuccinimide, peroxides iii) CH3ONa, CH3OH, heat iv) m-CPBA v) CH3MgBr vi) NH4Cl + Cl I IV II V III HO HO HO HO Br a) I b) II c) III d) IV e) V Answer: D Topic: Reaction products Section: 15.6, 15.12, 15.13 Difficulty Level: Hard 100) What product would result from the following series of reactions, 60 ? i) HF ii) N-Bromosuccinimide, peroxides iii) CH3ONa, CH3OH, heat iv) m-CPBA v) CH3MgBr vi) NH4Cl + I IV II V III HO HO HO HO Br a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 15.6, 15.12, 15.13 Difficulty Level: Hard 101) What product would result from the following series of reactions, 61 ? i) BF3 ii) N-Bromosuccinimide, peroxides iii) CH3ONa, CH3OH, heat iv) m-CPBA v) CH3MgBr vi) NH4Cl + OH I IV II V III HO HO HO HO Br a) I b) II c) III d) IV e) V Answer: D Topic: Reaction Products Section: 15.6, 15.12, 15.13 Difficulty Level: Hard 102) Which of the following is not a meta-directing substituent when present on the benzene ring? a) -NHCOCH3 b) -NO2 c) -N(CH3)3 + d) -CN e) -CO2H Answer: A Topic: Directing Effects Section: 15.10 Difficulty Level: Easy 62 103) Which of the following is not a meta-directing substituent when present on the benzene ring? a) -N=O b) -NO2 c) -N(CH3)3 + d) -CN e) -CO2H Answer: A Topic: Directing Effects Section: 15.10 Difficulty Level: Easy 104) Each of the five disubstituted benzenes shown below is nitrated. In which of these cases does the arrow not indicate the chief position of nitration. C l O H C O O H C l N H C O C H 3 C H 3 C C H 3 C H 2 C H 3 N O 2 C l O I I I I I I I V V a) I b) II c) III d) IV e) V Answer: C Topic: Directing Effects Section: 15.14 Difficulty Level: Easy 105) Which of the following compounds would yield the greatest amount of meta product when subjected to ring nitration? 63 I II III IV V HO O OH O O HO HO O HO O a) I b) II c) III d) IV e) V Answer: A Topic: Directing Effects Section: 15.10 Difficulty Level: Easy 106) Which of the following is not an ortho-para director in electrophilic aromatic substitution? a) -CF3 b) -OCH3 c) -CH3 d) -F e) -NH2 Answer: A Topic: Directing Effects Section: 15.10 Difficulty Level: Easy 107) Which of the following is not an ortho-para director in electrophilic aromatic substitution? a) -CCl3 b) -OCH3 c) -CH3 d) -F e) -NH2 Answer: A 64 Topic: Directing Effects Section: 15.10 Difficulty Level: Easy 108) Which of the following is not an ortho-para director in electrophilic aromatic substitution? a) -SO3H b) -OCH3 c) -CH3 d) -F e) -NH2 Answer: A Topic: Directing Effects Section: 15.10 Difficulty Level: Easy 109) Which of the following is not an ortho-para director in electrophilic aromatic substitution? a) b) -OCH3 c) -CH3 d) -F e) -NH2 Answer: A Topic: Directing Effects Section: 15.10 Difficulty Level: Easy 110) Which is the best prediction of the site(s) of substitution when 3-methylphenol is nitrated? a) C-2 b) C-4 c) C-5 d) C-6 e) C-4 and C-6 Answer: E 65 Topic: Directing Effects Section: 15.10 Difficulty Level: Easy 111) (Trifluoromethyl)benzene, C6H5CF3, will a) nitrate rapidly in the ortho-para positions. b) nitrate slowly in the ortho-para positions. c) nitrate rapidly in the meta position. d) nitrate slowly in the meta position. e) fail to nitrate under any conditions. Answer: D Topic: Directing Effects Section: 15.10 Difficulty Level: Easy 112) What feature is common to all meta-directing groups? a) The atom directly attached to the ring has a full or well-developed partial positive charge. b) The atom directly attached to the ring is doubly bonded to oxygen. c) One or more halogen atoms are present in the group. d) One or more oxygen atoms are present in the group. e) The group is attached to the ring through a carbon atom. Answer: A Topic: Directing Effects Section: 15.10 and 15.11 Difficulty Level: Easy 113) Which of these compounds gives essentially a single product on electrophilic substitution of a third group? a) p-chlorotoluene b) m-ethylanisole c) 1-bromo-2-chlorobenzene d) m-xylene e) 3-hydroxybenzoic acid Answer: D 66 Topic: Directing Effects Section: 15.10 Difficulty Level: Medium 114) Arrange the following compounds in order of decreasing reactivity in electrophilic substitution: O O Br NO2 I II III IV V a) V > II > I > III > IV b) II > V > III > I > IV c) IV > I > III > V > II d) III > II > I > IV > V e) IV > V > II > I > III Answer: B Topic: Directing Effects Section: 15.10 Difficulty Level: Medium 115) What is a feature found in all ortho-para directing groups? a) An oxygen atom is directly attached to the aromatic ring. b) The atom attached to the aromatic ring must possess an unshared pair of electrons. c) The group has the ability to delocalize the positive charge of the arenium ion. d) The atom directly attached to the aromatic ring is more electronegative than carbon. e) The group contains a multiple bond. Answer: C Topic: Directing Effects Section: 15.11 Difficulty Level: Medium 116) The ortho/para product ratio is expected to be the smallest for the bromination of which of these? a) Toluene b) Isopropylbenzene c) Butylbenzene 67 d) sec-Butylbenzene e) tert-Butylbenzene Answer: E Topic: Directing Effects Section: 15.10 and 15.15 Difficulty Level: Medium 117) Which reagent(s) would you use to carry out the following transformation? isopropylbenzene 2- and 4-chloro-1-isopropylbenzene a) Cl2, light, and heat b) Cl2, FeCl3 c) SOCl2 d) C2H5Cl, AlCl3 e) HCl, peroxides Answer: B Topic: Reagents Section: 15.3 and 15.10 Difficulty Level: Medium 118) Which reagent(s) would you use to carry out the following transformation? ethylbenzene 2- and 4-chloro-1-ethylbenzene a) Cl2, light, and heat b) Cl2, FeCl3 c) SOCl2 d) C2H5Cl, AlCl3 e) None of these choices. Answer: B Topic: Reagents Section: 15.3 and 15.10 Difficulty Level: Medium 119) Which reagent(s) would you use to carry out the following transformation? t-butylbenzene p-chloro substitution product a) Cl2, light, and heat 68 b) Cl2, FeCl3 c) SOCl2 d) C2H5Cl, AlCl3 e) HCl, peroxide Answer: B Topic: Reagents Section: 15.3 and 15.10 Difficulty Level: Medium 120) Which reagent(s) would you use to carry out the following transformation? ethylbenzene 1-chloro-1-phenylethane a) Cl2, light, or heat b) Cl2, FeCl3 c) SOCl2 d) C2H5Cl, AlCl3 e) HCl, O2 Answer: A Topic: Reagents Section: 15.12 Difficulty Level: Medium 121) Which reagent(s) would you use to synthesize 2- and 4-bromo-1-cyclopentylbenzene from cyclopentylbenzene? a) N-Bromosuccinimide (NBS), CCl4, light b) PBr3 c) Br2, FeBr3 d) CH3CH2Br, AlBr3 e) HBr, ROOR Answer: C Topic: Reagents Section: 15.3 and 15.10 Difficulty Level: Medium 122) Which reagent would you use to carry out the following transformation? tert-butylbenzene p-tert-butylbenzenesulfonic acid 69 + o-tert-butylbenzenesulfonic acid a) HNO3/H2SO4 b) tert-C4H9Cl/AlCl3 c) H2SO3/peroxides d) SO3/H2SO4 e) SO2/H2SO3 Answer: D Topic: Reagents Section: 15.5 and 15.10 Difficulty Level: Medium 123) Which reagent(s) would you use to carry out the following transformation? toluene benzoic acid a) Br2, heat, and light b) Cl2, FeCl3 c) KMnO4, OH- , heat (then H3O + ) d) HNO3/H2SO4 e) SO3/H2SO4 Answer: C Topic: Reagents Section: 15.13 Difficulty Level: Medium 124) Which reagent(s) would you use to carry out the following transformation? ethylbenzene benzoic acid a) Cl2, light, and heat b) Cl2, FeCl3 c) KMnO4, OH- , heat (then H3O + ) d) HNO3/H2SO4 e) SO3/H2SO4 Answer: C Topic: Reagents Section: 15.13 Difficulty Level: Medium 70 125) Which reagent(s) would you use to carry out the following transformation? cumene 2- and 4-chlorocumene a) Cl2, light, and heat b) Cl2, FeCl3 c) SOCl2 d) C2H5Cl, AlCl3 e) HCl, peroxides Answer: B Topic: Reagents Section: 15.3 and 15.10 Difficulty Level: Hard 126) Which reagent(s) would you use to carry out the following transformation? toluene benzyl bromide a) Br2, FeBr3 b) N-Bromosuccinimide, ROOR, h c) HBr d) Br2/CCl4 e) NaBr, H2SO4 Answer: B Topic: Reagents Section: 15.12 Difficulty Level: Hard 127) The compound 4-bromo-1-propylbenzene is best made from benzene by the application of these reagents in the order shown: a) (1) Br2,Fe (2) CH3CH2CH2Cl, AlCl3 b) (1) CH3CH2CH2Cl, AlCl3 (2) Br2,Fe c) C H 3 C H 2 C C l O 1 ) , A l C l 3 2 ) B r 2 , F e 3 ) Z n ( H g ) , H C l d) C H 3 C H 2 C C l O 1 ) , A l C l 3 3 ) B r 2 2 ) Z n ( H g ) , H C l , F e e) (1) (CH3)2CHCl, AlCl3 (2) Br2,Fe 71 Answer: D Topic: Reagents Section: 15.14 Difficulty Level: Hard 128) The compound 4-bromo-1-propylbenzene is best made from benzene by the application of these reagents in the order shown: a) (1) Br2,Fe (2) CH3CH2CH2Cl, AlCl3 b) (1) CH3CH2CH2Cl, AlCl3 (2) Br2,Fe c) C H 3 C H 2 C C l O 1 ) , A l C l 3 2 ) B r 2 , F e 3 ) Z n ( H g ) , H C l d) e) (1) (CH3)2CHCl, AlCl3 (2) Br2,Fe Answer: D Topic: Reagents Section: 15.14 Difficulty Level: Hard 129) Which of the following compounds would be most reactive toward electrophilic substitution? OH CH3 Br CHO NO2 I II III IV V a) I b) II c) III d) IV e) V Answer: A Topic: Relative Reactivities Section: 15.11 Difficulty Level: Easy 72 130) Which of the following compounds would be least reactive toward electrophilic substitution? OH CH3 Br CHO NO2 I II III IV V a) I b) II c) III d) IV e) V Answer: E Topic: Relative Reactivities Section: 15.11 Difficulty Level: Easy 131) Which of the following compounds would be most reactive to ring bromination? CH3 NO2 CF3 Cl NH2 I II III IV V a) I b) II c) III d) IV e) V Answer: E Topic: Relative Reactivities Section: 15.11 Difficulty Level: Easy 132) Which of the following compounds would be least reactive toward electrophilic substitution? 73 NO2 NO2 O NH O I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Relative Reactivities Section: 15.11 Difficulty Level: Easy 133) Which of the following compounds would be most reactive toward electrophilic substitution? NO2 NO2 O NH O NH2 I II III IV V a) I b) II c) III d) IV e) V Answer: E Topic: Relative Reactivities Section: 15.11 Difficulty Level: Easy 134) Which of the following compounds would be most reactive toward ring nitration? 74 O O CF3 OH NH O I II III IV V a) I b) II c) III d) IV e) V Answer: D Topic: Relative Reactivities Section: 15.11 Difficulty Level: Easy 135) Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring bromination? OH HO O NH2 OCH3 CH3 I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Relative Reactivities Section: 15.11 Difficulty Level: Easy 136) Which of the following compounds would be most reactive toward ring bromination? 75 O O HO O NH2 OCH3 O O O I II III IV V a) I b) II c) III d) IV e) V Answer: C Topic: Relative Reactivities Section: 15.11 Difficulty Level: Easy 137) Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring nitration? O O NH OCH3 CH3 I II III IV V a) I b) II c) III d) IV e) V Answer: B Topic: Relative Reactivities Section: 15.11 Difficulty Level: Easy 138) Which of the following compounds would you expect to be most reactive toward ring nitration? a) Benzene b) Toluene 76 c) m-Xylene d) p-Xylene e) Benzoic acid Answer: C Topic: Relative Reactivities Section: 15.11 Difficulty Level: Medium 139) Which of the following compounds would you expect to be most reactive toward ring nitration? a) Benzene b) Toluene c) m-Xylene d) o-Xylene e) Benzoic acid Answer: C Topic: Relative Reactivities Section: 15.11 Difficulty Level: Medium 140.)Which of the following structures would not be a contributor to the resonance hybrid of the benzyl cation? CH3 II CH2 III CH2 IV CH3 IV + + CH3 I + H + + H a) I b) II c) III d) IV e) V Answer: A Topic: Non-EAS Relative Rates and Intermediates Section: 15.12 77 Difficulty Level: Medium 141) Which of the following carbocations would be most stable? a) C 6 H 5 C H 2 C H 2 C H C H 2 C H 3 b) C 6 H 5 C H 2 C H 2 C H C H 3 C H 2 c) C 6 H 5 C H 2 C H 2 C C H 3 C H 3 d) C 6 H 5 C H 2 C H C H C H 3 C H 3 e) C 6 H 5 C H C H 2 C H C H 3 C H 3 Answer: E Topic: Non-EAS Relative Rates and Intermediates Section: 15.12 Difficulty Level: Medium 142) Which alkyl halide would be most reactive in an SN2 reaction? a) C6H5CH2CH2CH2Br b) C 6 H 5 C H C H 2 B r C H 3 c) C 6 H 5 C H 2 C H C H 3 B r d) C 6 H 5 C C H 2 B r C H 3 C H 3 e) C 6 H 5 C C H 3 B r C H 3 78 Answer: A Topic: Non-EAS Relative Rates and Intermediates Section: 15.15 Difficulty Level: Medium 143) Which alkyl halide would be most reactive in an SN1 reaction? a) C6H5CH2CH2CH2Br b) C 6 H 5 C H 2 C H C H 3 B r c) C 6 H 5 C H 2 C B r C H 3 C H 3 d) C 6 H 5 C C H 3 B r C H 3 e) C 6 H 5 C C H 2 B r C H 3 C H 3 Answer: D Topic: Non-EAS Relative Rates and Intermediates Section: 15.15 Difficulty Level: Medium 144) The rate of solvolysis in ethanol is least for which of these compounds? a) C6H5CH2Cl b) C 6 H 5 C ( C H 3 ) 2 C l c) (C6H5)2CHCl d) C 6 H 5 C H C l C H 3 e) (C6H5)3CCl Answer: A 79 Topic: Non-EAS Relative Rates and Intermediates Section: 15.15 Difficulty Level: Medium 145) Which of these species is/are proposed as intermediate(s) in the mechanism for the Birch reduction? a) Radical b) Carbanion c) Radical anion d) Two of these choices. e) All of these choices. Answer: E Topic: Non-EAS Relative Rates and Intermediates Section: 15.16 Difficulty Level: Hard 146) Benzoic acid can be prepared by the oxidation of all of the following compounds except this one: a) C6H5CH=CH2 b) C6H5CCH c) C6H5COCH3 d) C6H5CH2CH2CH3 e) C6H5C(CH3)3 Answer: E Topic: Synthesis Section: 15.13 Difficulty Level: Easy 147) Benzoic acid can be prepared by the oxidation of which of the following compounds: a) C6H5CH=CH2 b) C6H5CCH c) C6H5COCH3 d) C6H5CH2CH2CH3 e) All of these choices. 80 Answer: E Topic: Synthesis Section: 15.13 Difficulty Level: Easy 148) Benzoic acid can be prepared by the oxidation of which of the following compounds: a) C6H5CH=CH2 b) C6H5CCH c) C6H5COCH3 d) C6H5CH(CH3)2 e) All of these choices. Answer: E Topic: Synthesis Section: 15.13 Difficulty Level: Easy 149) Which of these is a satisfactory synthesis of 1-bromo-2-phenylethane? a) C6H5CH2CH3 + Br2, Fe3+ b) C6H5CH2CH3 + Br2, 400C c) C6H5CH2CH2OH + Br2, CCl4 d) C6H5CH=CH2 + HBr, ROOR e) C6H5CH2CH3 + NBS, ROOR Answer: D Topic: Synthesis Section: 15.13 Difficulty Level: Medium 150) What reagent can effect the following transformation? CO2H Br Br CO2H CO2H Br Br ? a) CO2; then H3O + b) H3O + , heat 81 c) Mg; then CO2; then H3O + d) H2O2, heat e) KMnO4, OH- , heat; then H3O + Answer: E Topic: Synthesis Section: 15.13 Difficulty Level: Medium 151) A good synthesis of ( C H 3 ) 3 C C C H 3 O would be: a) B e n z e n e C H 3 C C l O A l C l 3 ( C H 3 ) 3 C C l A l C l 3 b) B e n z e n e C H 3 C C l O A l C l 3 ( C H 3 ) 3 C C l A l C l 3 c) B e n z e n e C H 3 C C l O A l C l 3 H F ( C H 3 ) 2 C C H 2 d) More than one of these choices. e) None of these choices. Answer: B Topic: Synthesis Section: 15.14 Difficulty Level: Medium 152) Which would be a good synthesis of m-nitrobenzoic acid? a) B e n z e n e H N O 3 / H 2 S O 4 h e a t A l C l 3 C H 3 C l 1 . K M n O 4 , N a O H , h e a t 2 . H 3 O + 82 b) T o l u e n e H N O 3 / H 2 S O 4 h e a t 1 . K M n O 4 , N a O H , h e a t 2 . H 3 O + c) T o l u e n e H N O 3 / H 2 S O 4 h e a t 1 . K M n O 4 , N a O H , h e a t 2 . H 3 O + d) More than one of these choices. e) None of these choices. Answer: C Topic: Synthesis Section: 15.14 Difficulty Level: Medium 153) Which of the following would be the best synthesis of 1,4-dimethyl-2-nitrobenzene? a) B e n z e n e H N O 3 H 2 S O 4 p r o d u c t 2 C H 3 C l 2 A l C l 3 b) T o l u e n e H N O 3 H 2 S O 4 p r o d u c t C H 3 C l A l C l 3 c) p - X y l e n e H N O 3 H 2 S O 4 d) C H 3 C l A l C l 3 m - N i t r o t o l u e n e e) All of these choices are equally good. Answer: C Topic: Nomenclature, Synthesis Section: 15.14 Difficulty Level: Hard 154) Starting with benzene, the best method for preparing p-nitrobenzoic acid is: a) HNO3/H2SO4; then CH3Cl/AlCl3; then separation of isomers; then KMnO4/ -OH/heat, followed by H3O + . b) CH3Cl/AlCl3; then HNO3/H2SO4; then separation of isomers; then KMnO4/ -OH/heat, followed by H3O + . c) CH3Cl/AlCl3; then KMnO4/ -OH/heat, followed by H3O + ; then HNO3/H2SO4. d) HNO3/H2SO4; then KMnO4/ -OH/heat, followed by H3O + ; then CH3Cl/AlCl3. 83 e) HNO3/H2SO4; then CO2, followed by H3O + . Answer: B Topic: Synthesis Section: 15.14 Difficulty Level: Hard 155) Starting with benzene, the best method for preparing m-nitrobenzoic acid is: a) HNO3/H2SO4; then CH3Cl/AlCl3; then separation of isomers; then KMnO4/ -OH/heat, followed by H3O + . b) CH3Cl/AlCl3; then HNO3/H2SO4; then separation of isomers; then KMnO4/ -OH/heat, followed by H3O + . c) CH3Cl/AlCl3; then KMnO4/ -OH/heat, followed by H3O + ; then HNO3/H2SO4. d) HNO3/H2SO4; then KMnO4/ -OH/heat, followed by H3O + ; then CH3Cl/AlCl3. e) HNO3/H2SO4; then CO2, followed by H3O + . Answer: C Topic: Synthesis Section: 15.14 Difficulty Level: Hard 156) How might the following synthesis be carried out: B e n z e n e C H 2 C H 3 C l s e v e r a l s t e p s ? a) C H 3 C H 2 C l C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t b) C H 3 C H 2 C l C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t c) C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t C H 3 C C l O Z n ( H g ) H C l d) C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t C H 3 C C l O Z n ( H g ) H C l e) None of these syntheses is satisfactory. 84 Answer: C Topic: Synthesis Section: 15.14 Difficulty Level: Hard 157) How might the following synthesis be carried out: B e n z e n e C H 2 C H 3 C l s e v e r a l s t e p s ? a) C H 3 C H 2 C l C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t b) C H 3 C H 2 C l C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t c) d) C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t C H 3 C C l O Z n ( H g ) H C l e) None of these syntheses is satisfactory. Answer: C Topic: Synthesis Section: 15.14 Difficulty Level: Hard 158) How might the following synthesis be carried out: several steps Cl 85 a) C H 3 C H 2 C l C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t b) C H 3 C H 2 C l C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t c) C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t C H 3 C C l O Z n ( H g ) H C l d) C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t C H 3 C C l O Z n ( H g ) H C l e) None of these syntheses is satisfactory. Answer: D Topic: Synthesis Section: 15.14 Difficulty Level: Hard 159) How might the following synthesis be carried out: several steps Cl a) C H 3 C H 2 C l C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t b) C H 3 C H 2 C l C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t c) C 6 H 6 A l C l 3 C l 2 F e C l 3 p r o d u c t C H 3 C C l O Z n ( H g ) H C l d) e) None of these syntheses is satisfactory. 86 Answer: D Topic: Synthesis Section: 15.14 Difficulty Level: Hard [Show Less]