Multiple Choice Rank the following in order of increasing rate of electrophilic aromatic bromination (slowest to fastest). 352views
Textbook Questionp-Xylene undergoes nitration much faster than benzene. Use resonance forms of the sigma complex to explain this accelerated rate834views
Textbook QuestionFor each horizontal row of substituted benzenes, indicate a. the one that is the most reactive in an electrophilic aromatic substitution reaction. 467views
Textbook QuestionList the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution: b. dichloromethylbenzene, difluoromethylbenzene, toluene, chloromethylbenzene495views
Textbook QuestionList the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution: a. benzene, phenol, toluene, nitrobenzene, bromobenzene1147views1rank
Textbook QuestionRank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution: b. 1-chloro-2,4-dinitrobenzene, 2,4-dinitrophenol, 1-methyl-2,4-dinitrobenzene444views
Textbook QuestionRank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution: e. p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethylbenzene469views
Textbook QuestionRank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution: f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene531views
Textbook QuestionFor each horizontal row of substituted benzenes, indicate b. the one that is the least reactive in an electrophilic aromatic substitution reaction.422views
Textbook QuestionFor each horizontal row of substituted benzenes, indicate b. the one that is the least reactive in an electrophilic aromatic substitution reaction.425views
Textbook QuestionWhy is anisole nitrated more rapidly than thioanisole under the same conditions?508views
Textbook QuestionA mixture of 0.10 mol benzene and 0.10 mol p-xylene was allowed to react with 0.10 mol nitronium ion until all the nitronium ion was gone. Two products were obtained: 0.002 mol of one and 0.098 mol of the other. b. Why was more of one product obtained than of the other?323views
Textbook Question(••) Indigo is a dye that was originally isolated from coal tar. In 1905, Johann Friedrich Wilhelm Adolf von Baeyer won a Nobel Prize for a method that allowed indigo to be isolated from plants [a green chemist ahead of his time.] If you nitrated indigo using the reaction learned in this chapter, at which carbon would you expect the nitro group to attach?<IMAGE> 350views
Textbook QuestionSubstitution at the benzylic position of the molecules shown was observed to occur at different rates. Explain this observation.384views
Textbook QuestionPredict the mononitration products of the following compounds.(d) p-methoxybenzoic acid238views
Textbook QuestionPredict the mononitration products of the following compounds.(e) m-cresol (m-methylphenol)233views
Textbook QuestionPredict the mononitration products of the following compounds.(f) o-hydroxyacetophenone255views
Textbook QuestionAre the following substituents ortho–para directors or meta directors? d. COOH e. CF3 f. N=O445views
Textbook QuestionUsing resonanOce contributors for the carbocation intermediate, explain why a phenyl group is an ortho–para director.358views
Textbook QuestionFor each of the following compounds, indicate the ring carbon(s) that is/are nitrated when the compound is treated with HNO3/H2SO4: e. f.429views
Textbook Questiona. Does a coupling reaction have to be used to synthesize p-dipropylbenzene? b. Can a coupling reaction be used to synthesize p-dipropylbenzene?430views
Textbook QuestionWhat products are obtained from the reaction of the following compounds with one equivalent of Br2, using FeBr3 as a catalyst? c. d. 544views
Textbook QuestionRank the following compounds from most reactive to least reactive in an electrophilic aromatic substitution reaction: <s>840views
Textbook QuestionFor each of the statements in Column I, choose a substituent from Column II that fits the description for the compound on the right:353views
Textbook QuestionPredict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark. (a) 1099views1rank
Textbook QuestionPredict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark. (b) 1211views1rank1comments
Textbook QuestionPredict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark. (C) 1209views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (f) fuming sulfuric acid1082views
Textbook QuestionBiphenyl is two benzene rings joined by a single bond. The site of substitution for a biphenyl is determined by (1) which phenyl ring is more activated (or less deactivated), and (2) which position on that ring is most reactive, using the fact that a phenyl substituent is activating and ortho, para-directing. (a) Use resonance forms of a sigma complex to show why a phenyl substituent should be ortho, para-directing.2182views
Textbook QuestionBiphenyl is two benzene rings joined by a single bond. The site of substitution for a biphenyl is determined by (1) which phenyl ring is more activated (or less deactivated), and (2) which position on that ring is most reactive, using the fact that a phenyl substituent is activating and ortho, para-directing. (b) Predict the mononitration products of the following compounds. (iv) 668views
Textbook QuestionBiphenyl is two benzene rings joined by a single bond. The site of substitution for a biphenyl is determined by (1) which phenyl ring is more activated (or less deactivated), and (2) which position on that ring is most reactive, using the fact that a phenyl substituent is activating and ortho, para-directing. (b) Predict the mononitration products of the following compounds. (v) 636views
Textbook QuestionBiphenyl is two benzene rings joined by a single bond. The site of substitution for a biphenyl is determined by (1) which phenyl ring is more activated (or less deactivated), and (2) which position on that ring is most reactive, using the fact that a phenyl substituent is activating and ortho, para-directing. (b) Predict the mononitration products of the following compounds. (vi) 1455views1rank
Textbook QuestionStep 2 of the iodination of benzene shows water acting as a base and removing a proton from the sigma complex. We did not consider the possibility of water acting as a nucleophile and attacking the carbocation, as in an electrophilic addition to an alkene. Draw the reaction that would occur if water reacted as a nucleophile and added to the carbocation. Explain why this type of addition is rarely observed.874views1rank
Textbook QuestionPropose a mechanism for the sulfonation of pyridine, and point out why sulfonation occurs at the 3-position.1234views2rank
Textbook QuestionShow how m-toluidine can be converted to the following compounds, using any necessary reagents. (e) 611views
Textbook Question(••••) The first step of a reaction called electrophilic aromatic substitution (see Chapter 23) is as follows: <IMAGE>If this step is rate-determining for the overall reaction, which benzene derivative would you expect to react most quickly? Which would react most slowly? [Use the information you gleaned from working Assessments 14.55–14.59.](a) <IMAGE>325views
Textbook QuestionThe nitro group directs electrophilic aromatic substitution to the meta position. After reduction by hydrogenation, to which carbon(s) does it direct?<IMAGE>384views1rank
Textbook QuestionPredict the major product of the following electrophilic aromatic substitution reactions.(b) <IMAGE> 412views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (i) iodine + HNO3502views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (d) bromine + a nail783views
Textbook QuestionDraw the product(s) of each of the following reactions: a. benzoic acid + HNO3/H2SO4 b. isopropylbenzene + Cl2 + FeCl3645views
Textbook QuestionWhat is the major product(s) of each of the following reactions? e. nitration of p-methoxybenzaldehyde f. nitration of p-tert-butylmethylbenzene449views
Textbook QuestionPredict the mononitration products of the following compounds. (a) o-nitrotoluene (b) m-chlorotoluene (c) o-bromobenzoic acid1013views1rank
Textbook QuestionGive the products, if any, of each of the following reactions: a. benzonitrile + methyl chloride + AlCl3 b. phenol + Br2672views
Textbook QuestionGive the products, if any, of each of the following reactions: c. benzoic acid + CH3CH2Cl + AlCl3 d. benzene + 2 CH3Cl + AlCl3505views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (g) 1-chloro-2,2-dimethylpropane + AlCl3682views
Textbook QuestionPropose products (if any) and mechanisms for the following AlCl3-catalyzed reactions: (c) 3-chloro-2,2-dimethylbutane with isopropylbenzene1851views
Textbook QuestionPredict the products (if any) of the following reactions. (a) (excess) benzene + isobutyl chloride + AlCl3860views
Textbook QuestionPredict the products (if any) of the following reactions. (b) (excess) toluene + butan-1-ol + BF31648views
Textbook QuestionWhich reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products. (d) benzamide (PhCONH2) + CH3CH2Cl (Desired Product: p-ethylbenzamide)571views
Textbook QuestionWhich reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products. (e) toluene + HNO3, H2SO4, heat (Desired Product: 2,4,6-trinitrotoluene (TNT))644views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (h) benzoyl chloride + AlCl3656views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (e) isobutylene + HF491views
Textbook QuestionPredict the major products of the following reactions. (a) 2,4-dinitrochlorobenzene + NaOCH3 617views
Textbook QuestionPredict the major products of the following reactions. (c) nitrobenzene + fuming sulfuric acid 656views
Textbook Question(••) LOOKING BACK In Chapter 23, we learned about the electrophilic aromatic nitration reaction. When phenol is subjected to these conditions with a large excess of nitric acid, a molecule called picric acid is produced. Predict the product of this reaction and explain why the pKₐ value of this compound is 0.38.<IMAGE>293views
Textbook QuestionPredict the major products of the following reactions.(b) phenol + tert-butyl chloride + AlCl3634views
Textbook Questionb. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.298views
Textbook QuestionRank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole210views
Textbook QuestionFor each horizontal row of substituted benzenes, indicatec. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.<IMAGE>193views
Textbook QuestionFor each horizontal row of substituted benzenes, indicatec. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.<IMAGE>137views
Textbook QuestionAre the following substituents ortho–para directors or meta directors?a. CH=CHC≡N b. NO2 c. CH2OH182views
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