Chapter 12 - Chapter 12: Reactions of Arenes Electrophilic...

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Chapter 12: Reactions of Arenes - Electrophilic Aromatic Substitution 1. What is the product of the following reaction? A) isobutylbenzene C) sec -butylbenzene B) 2-methyl-1-phenylpropene D) tert -butylbenzene 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. 3. Which of the following aromatic compounds reacts faster than benzene in electrophilic aromatic bromination? 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, meta B) slower, ortho,para C) faster, ortho,para D) faster, meta 5. Which one of the following is the electrophile in the reaction shown below? A) benzene B) NO 3 ¯ C) NO 2 + D) H 2 SO 4 6. What is the electrophile in the Friedel-Crafts alkylation reaction below? A) AlCl 3 B) Cl ¯ C) benzene D) (CH 3 ) 3 C + 7. Which point on the potential energy diagram corresponds to the species shown to the right for the electrophilic bromination of benzene with Br 2 /FeBr 3 ?
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8. Which species below best depicts the electrophile in the FeBr3-catalyzed bromination of benzene? A) Br 2 B) FeBr 4 - C) D) FeBr 3 9. Which one of the following reactions does not give tert - butylbenzene? A) benzene + (CH 3 ) 3 CCl/AlCl 3 B) benzene + (CH 3 ) 2 C=CH 2 /H 2 SO 4 C) benzene + (CH 3 ) 3 CH/AlCl 3 D) benzene + (CH 3 ) 3 COH/H 2 SO 4 10. Which point on the potential energy diagram corresponds to the species shown to the right for the electrophilic nitration of benzene with HNO 3 /H 2 SO 4 ? 11. What is(are) the product(s) of the following reaction? A) C 6 H 5 CH 2 CH 2 CH 3 B) C 6 H 5 CH(CH 3 ) 2 C) C 6 H 5 CH 2 CH 2 CH 2 Cl D) a mixture of C 6 H 5 CH 2 CH 2 CH 3 and C 6 H 5 CH(CH 3 ) 2 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 below? A) only 1 B) 2 C) 3 D) 4 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 B) IV > III > II > I C) II > I > IV > III D) II > III > IV > I
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15. Which of the following groups are ortho/para directors? I. –NO 2 II. –OCH 3 III. –CO 2 CH 3 IV. –CH 3 A) I and III B) II and III C) II and IV D) III and IV 16. Predict the effect the substituent attached to the benzene ring below would have on electrophilic aromatic substitution reactions? A) ortho/para director, activator B) ortho/para director, deactivator C) meta director, activator D) meta director, deactivator 17. In the Friedel-Crafts alkylation of benzene, dialkylation is often a significant byproduct. In the Friedel-Crafts acylation of benzene, diacylation is not a significant byproduct. Which of the following is the primary reason for this difference? A) Alkyl groups activate the ring to further substitution, acyl groups deactivate it.
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This note was uploaded on 06/30/2011 for the course CHEM 243 taught by Professor Adcock during the Summer '11 term at New River Community College.

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Chapter 12 - Chapter 12: Reactions of Arenes Electrophilic...

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