Multiple Choice Rank the following in order of increasing rate of electrophilic aromatic bromination (slowest to fastest). 350views
Textbook Questionp-Xylene undergoes nitration much faster than benzene. Use resonance forms of the sigma complex to explain this accelerated rate826views
Textbook QuestionFor each horizontal row of substituted benzenes, indicate a. the one that is the most reactive in an electrophilic aromatic substitution reaction. 460views
Textbook QuestionList the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution: b. dichloromethylbenzene, difluoromethylbenzene, toluene, chloromethylbenzene491views
Textbook QuestionList the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution: a. benzene, phenol, toluene, nitrobenzene, bromobenzene1136views1rank
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-dinitrobenzene438views
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-chloromethylbenzene466views
Textbook QuestionRank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution: f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene528views
Textbook QuestionFor each horizontal row of substituted benzenes, indicate b. the one that is the least reactive in an electrophilic aromatic substitution reaction.416views
Textbook QuestionFor each horizontal row of substituted benzenes, indicate b. the one that is the least reactive in an electrophilic aromatic substitution reaction.420views
Textbook QuestionWhy is anisole nitrated more rapidly than thioanisole under the same conditions?504views
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?320views
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> 348views
Textbook QuestionSubstitution at the benzylic position of the molecules shown was observed to occur at different rates. Explain this observation.376views
Textbook QuestionPredict the mononitration products of the following compounds.(d) p-methoxybenzoic acid231views
Textbook QuestionPredict the mononitration products of the following compounds.(e) m-cresol (m-methylphenol)229views
Textbook QuestionPredict the mononitration products of the following compounds.(f) o-hydroxyacetophenone250views
Textbook QuestionAre the following substituents ortho–para directors or meta directors? d. COOH e. CF3 f. N=O434views
Textbook QuestionUsing resonanOce contributors for the carbocation intermediate, explain why a phenyl group is an ortho–para director.354views
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.425views
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?425views
Textbook QuestionWhat products are obtained from the reaction of the following compounds with one equivalent of Br2, using FeBr3 as a catalyst? c. d. 539views
Textbook QuestionRank the following compounds from most reactive to least reactive in an electrophilic aromatic substitution reaction: <s>835views
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:348views
Textbook QuestionPredict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark. (a) 1092views1rank
Textbook QuestionPredict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark. (b) 1199views1rank1comments
Textbook QuestionPredict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark. (C) 1201views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (f) fuming sulfuric acid1078views
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.2167views
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) 665views
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) 635views
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) 1445views1rank
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.868views1rank
Textbook QuestionPropose a mechanism for the sulfonation of pyridine, and point out why sulfonation occurs at the 3-position.1222views2rank
Textbook QuestionShow how m-toluidine can be converted to the following compounds, using any necessary reagents. (e) 599views
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>323views
Textbook QuestionThe nitro group directs electrophilic aromatic substitution to the meta position. After reduction by hydrogenation, to which carbon(s) does it direct?<IMAGE>372views1rank
Textbook QuestionPredict the major product of the following electrophilic aromatic substitution reactions.(b) <IMAGE> 408views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (i) iodine + HNO3495views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (d) bromine + a nail774views
Textbook QuestionDraw the product(s) of each of the following reactions: a. benzoic acid + HNO3/H2SO4 b. isopropylbenzene + Cl2 + FeCl3643views
Textbook QuestionWhat is the major product(s) of each of the following reactions? e. nitration of p-methoxybenzaldehyde f. nitration of p-tert-butylmethylbenzene446views
Textbook QuestionPredict the mononitration products of the following compounds. (a) o-nitrotoluene (b) m-chlorotoluene (c) o-bromobenzoic acid999views1rank
Textbook QuestionGive the products, if any, of each of the following reactions: a. benzonitrile + methyl chloride + AlCl3 b. phenol + Br2667views
Textbook QuestionGive the products, if any, of each of the following reactions: c. benzoic acid + CH3CH2Cl + AlCl3 d. benzene + 2 CH3Cl + AlCl3502views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (g) 1-chloro-2,2-dimethylpropane + AlCl3679views
Textbook QuestionPropose products (if any) and mechanisms for the following AlCl3-catalyzed reactions: (c) 3-chloro-2,2-dimethylbutane with isopropylbenzene1836views
Textbook QuestionPredict the products (if any) of the following reactions. (a) (excess) benzene + isobutyl chloride + AlCl3854views
Textbook QuestionPredict the products (if any) of the following reactions. (b) (excess) toluene + butan-1-ol + BF31634views
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)570views
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))636views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (h) benzoyl chloride + AlCl3646views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (e) isobutylene + HF484views
Textbook QuestionPredict the major products of the following reactions. (a) 2,4-dinitrochlorobenzene + NaOCH3 613views
Textbook QuestionPredict the major products of the following reactions. (c) nitrobenzene + fuming sulfuric acid 645views
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>291views
Textbook QuestionPredict the major products of the following reactions.(b) phenol + tert-butyl chloride + AlCl3627views
Textbook Questionb. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.269views
Textbook QuestionRank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole206views
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>183views
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>130views
Textbook QuestionAre the following substituents ortho–para directors or meta directors?a. CH=CHC≡N b. NO2 c. CH2OH178views
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