Multiple Choice Rank the following in order of increasing rate of electrophilic aromatic bromination (slowest to fastest). 353views
Textbook Questionp-Xylene undergoes nitration much faster than benzene. Use resonance forms of the sigma complex to explain this accelerated rate838views
Textbook QuestionFor each horizontal row of substituted benzenes, indicate a. the one that is the most reactive in an electrophilic aromatic substitution reaction. 471views
Textbook QuestionList the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution: b. dichloromethylbenzene, difluoromethylbenzene, toluene, chloromethylbenzene497views
Textbook QuestionList the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution: a. benzene, phenol, toluene, nitrobenzene, bromobenzene1153views1rank
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-dinitrobenzene446views
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-chloromethylbenzene473views
Textbook QuestionRank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution: f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene534views
Textbook QuestionFor each horizontal row of substituted benzenes, indicate b. the one that is the least reactive in an electrophilic aromatic substitution reaction.424views
Textbook QuestionFor each horizontal row of substituted benzenes, indicate b. the one that is the least reactive in an electrophilic aromatic substitution reaction.430views
Textbook QuestionWhy is anisole nitrated more rapidly than thioanisole under the same conditions?512views
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> 353views
Textbook QuestionSubstitution at the benzylic position of the molecules shown was observed to occur at different rates. Explain this observation.389views
Textbook QuestionPredict the mononitration products of the following compounds.(d) p-methoxybenzoic acid240views
Textbook QuestionPredict the mononitration products of the following compounds.(e) m-cresol (m-methylphenol)235views
Textbook QuestionPredict the mononitration products of the following compounds.(f) o-hydroxyacetophenone257views
Textbook QuestionAre the following substituents ortho–para directors or meta directors? d. COOH e. CF3 f. N=O449views
Textbook QuestionUsing resonanOce contributors for the carbocation intermediate, explain why a phenyl group is an ortho–para director.359views
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.431views
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?431views
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>843views
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) 1104views1rank
Textbook QuestionPredict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark. (b) 1215views1rank1comments
Textbook QuestionPredict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark. (C) 1212views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (f) fuming sulfuric acid1089views
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.2193views
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) 641views
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) 1459views1rank
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.877views1rank
Textbook QuestionPropose a mechanism for the sulfonation of pyridine, and point out why sulfonation occurs at the 3-position.1240views2rank
Textbook QuestionShow how m-toluidine can be converted to the following compounds, using any necessary reagents. (e) 613views
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>328views
Textbook QuestionThe nitro group directs electrophilic aromatic substitution to the meta position. After reduction by hydrogenation, to which carbon(s) does it direct?<IMAGE>388views1rank
Textbook QuestionPredict the major product of the following electrophilic aromatic substitution reactions.(b) <IMAGE> 414views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (i) iodine + HNO3505views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (d) bromine + a nail786views
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-butylmethylbenzene451views
Textbook QuestionPredict the mononitration products of the following compounds. (a) o-nitrotoluene (b) m-chlorotoluene (c) o-bromobenzoic acid1014views1rank
Textbook QuestionGive the products, if any, of each of the following reactions: a. benzonitrile + methyl chloride + AlCl3 b. phenol + Br2676views
Textbook QuestionGive the products, if any, of each of the following reactions: c. benzoic acid + CH3CH2Cl + AlCl3 d. benzene + 2 CH3Cl + AlCl3507views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (g) 1-chloro-2,2-dimethylpropane + AlCl3684views
Textbook QuestionPropose products (if any) and mechanisms for the following AlCl3-catalyzed reactions: (c) 3-chloro-2,2-dimethylbutane with isopropylbenzene1854views
Textbook QuestionPredict the products (if any) of the following reactions. (a) (excess) benzene + isobutyl chloride + AlCl3866views
Textbook QuestionPredict the products (if any) of the following reactions. (b) (excess) toluene + butan-1-ol + BF31652views
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)572views
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))656views
Textbook QuestionPredict the major products formed when benzene reacts (just once) with the following reagents. (h) benzoyl chloride + AlCl3662views
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 621views
Textbook QuestionPredict the major products of the following reactions. (c) nitrobenzene + fuming sulfuric acid 662views
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>296views
Textbook QuestionPredict the major products of the following reactions.(b) phenol + tert-butyl chloride + AlCl3641views
Textbook Questionb. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.313views
Textbook QuestionRank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole211views
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>199views
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>141views
Textbook QuestionAre the following substituents ortho–para directors or meta directors?a. CH=CHC≡N b. NO2 c. CH2OH183views
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