11 11 2024 13 15 Chapter 12 carey Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution 1 What is the product of the following reaction isobutylbenzene 2 methyl 1 phenylpropene C D sec butylbenzene tert butylbenzene A B Ans D 2 The major product s in the nitration of benzoic acid is are A mixture of ortho and para nitrobenzoic acid B nitrobenzene C meta nitrobenzoic acid D nitrobenzene and para nitrobenzoic acid Ans C aromatic bromination 3 Which of the following aromatic compounds reacts faster than benzene in electrophilic A A B B C C D D Ans C Page 170 about blank 1 30 11 11 2024 13 15 Chapter 12 carey Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution 4 Nitration of benzoic acid has a reaction rate which is than the nitration rate of benzene and gives primarily the product s A slower faster meta C ortho para B slower ortho para D faster meta Ans A 5 Which one of the following is the electrophile in the reaction shown below A benzene B NO C NO D H Ans C 2 3 2SO4 6 What is the electrophile in the Friedel Crafts alkylation reaction below A AlCl B Cl C benzene D CH Ans D 3 3 3C 7 Which point on the potential energy diagram corresponds to the species shown to the right for the electrophilic bromination of benzene with Br2 FeBr 3 A A B B C C D D Ans B Page 171 about blank 2 30 11 11 2024 13 15 Chapter 12 carey Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution 8 Which species below best depicts the electrophile in the FeBr catalyzed bromination of 3 benzene A B Ans C A Br B FeBr C 2 Ans C 4 D FeBr 3 9 Which one of the following reactions does not give tert butylbenzene benzene CH 3 3CCl AlCl3 benzene CH 3 3CH AlCl3 benzene CH 3 2C CH H SO 2 2 4 benzene CH 3 3COH H SO2 4 C D 10 Which point on the potential energy diagram corresponds to the species shown to the right for the electrophilic nitration of benzene with HNO3 H SO 4 2 A A B B C C D D Ans C 11 What is are the product s of the following reaction C6H CH CH CH 2 2 5 3 C6H CH CH 5 3 2 C6H CH CH CH C1 2 2 2 5 A B C D Ans D a mixture of C 6H5CH CH CH 2 2 and C 6H CH CH 5 3 2 3 Page 172 about blank 3 30 11 11 2024 13 15 Chapter 12 carey Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution 12 Which one of the following is not a resonance form of the cyclohexadienyl cation intermediate in the bromination of benzene 13 How many mononitration products are possible in the nitration of naphthalene shown A A B B C C D D Ans B below A only 1 B 2 C 3 D 4 Ans B 14 Rank the following compounds in order of decreasing reactivity to aromatic electrophilic bromination I benzene II toluene III benzoic acid IV phenol A IV II I III C II I IV III B IV III II I D II III IV I Ans A 15 Which of the following groups are ortho para directors 2 I NO II OCH III CO A I and III B II and III C II and IV D III and IV Ans C IV CH 2CH3 3 3 Page 173 about blank 4 30 11 11 2024 13 15 Chapter 12 carey Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution 16 Predict the effect the substituent attached to the benzene ring below would have on electrophilic aromatic substitution reactions A B Ans D Ans A ortho para director activator C meta director activator ortho para director deactivator D meta director deactivator 17 In the Friedel Crafts alkylation of benzene dialkylation is often a significant by product In the Friedel Crafts acylation of benzene diacylation is not a significant by product Which of the following is the primary reason for this difference A Alkyl groups activate the ring to further substitution acyl groups deactivate it B Alkyl groups are less sterically hindered than acyl groups C Acyl cations are more difficult to make with Lewis acids D Unlike acyl cations carbocations can undergo rearrangements 18 Which of the following is the best method to make n butylbenzene A A B B C C D D Ans C Page 174 about blank 5 30 11 11 2024 13 15 Chapter 12 carey Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution 19 What is the major product of the following reaction A B 4 ethyl 2 nitrophenol 4 ethyl 3 nitrophneol Ans A C D 1 ethyl 4 nitrobenzene 4 nitrophenol 20 Based on resonance theory what is the approximate charge on the indicated carbon A 1 B 0 50 C 0 33 D 0 20 Ans C 21 Which isomer of dichlorobenzene gives a single mononitration product A ortho B meta C para D none of them Ans C 22 Arrange the following compounds in order of increasing reaction rate with 2 3 6H5 HNO H SO 4 I C CH O II C I III IV II A B I IV III II Ans A 6H OCH5 3 III C Br IV C 6H5 6H5CH3 III I II IV III I IV II C D Page 175 about blank 6 30 11 11 2024 13 15 Chapter 12 carey Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution 23 Salicylic acid reacts with two equivalents of ICl to give one of the products below Which one is it Hint Cl is more electronegative than I A A B B C C D D Ans D 24 Identify the preferred site s of electrophilic attack on the following compound A ortho para positions on ring 1 C ortho para positions on ring 2 B meta position on ring 1 D meta position on ring 2 Ans C benzene 25 Which of the following is the best method to make meta bromoethylbenzene from A A B B C C D D Ans D Page 176 about blank 7 30 11 11 2024 13 15 Chapter 12 carey Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution 26 Which one of the following compounds undergoes electrophilic aromatic sulfonation at the fastest rate A A B B C C D D Ans D 27 What is the product of the following series of reactions A A B B C C D D Ans B Page 177 about blank 8 30 11 11 2024 13 15 Chapter 12 carey Chapter 12 Reactions of Arenes Electrophilic Aromatic Substitution 28 Nitration of chlorobenzene has a reaction rate which is than the nitration rate of benzene and gives primarily the product s A faster ortho para B faster meta C slower ortho para D slower meta Ans C 29 What is the major product of the Friedel Crafts …