21%20Ch15 - CHAPTER 15 Reactions of Substituted Benzenes...

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425 CHAPTER 15 Reactions of Substituted Benzenes Important Terms activating substituent a substituent that increases the reactivity of an aromatic ring. Electron-donating substituents activate aromatic rings toward electrophilic attack, and electron- withdrawing substituents activate aromatic rings toward nucleophilic attack. arenediazonium salt Ar N N X + azo linkage an − − NN bond. benzyne intermediate a compound with a triple bond in place of one of the double bonds of benzene. cine substitution substitution at the carbon adjacent to the carbon that was bonded to the leaving group. deactivating substituent a substituent that decreases the reactivity of an aromatic ring. Electron- withdrawing substituents deactivate aromatic rings toward electrophilic attack, and electron-donating substituents deactivate aromatic rings toward nucleophilic attack. direct substitution substitution at the carbon that was bonded to the leaving group. donate electrons by donation of electrons through p orbital overlap with neighboring π bonds. resonance fused rings rings that share two adjacent carbons. inductive electron donation of electrons through a σ bond. donation inductive electron withdrawal of electrons through a σ bond. withdrawal meta director a substituent that directs an incoming substituent meta to an existing substituent. nitrosamine an amine with a nitroso (N O) substituent bonded to its nitrogen atom. (N -nitroso compound) nucleophilic aromatic a reaction in which a nucleophile substitutes for an atom or group bonded to an substitution aromatic ring. ortho-para director a substituent that directs an incoming substituent ortho and para to an existing substituent. resonance electron donation of electrons through p orbital overlap with neighboring π bonds. donation
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426 Chapter 15 resonance electron withdrawal of electrons through p orbital overlap with neighboring π bonds. withdrawal Sandmeyer reaction the reaction of an arenediazonium ion with a cuprous salt. Schiemann reaction the reaction of an arenediazonium ion with 4 HBF . S N Ar reaction a nucleophilic aromatic substitution reaction. withdraw electrons by withdrawal of electrons through p orbital overlap with neighboring π bonds. resonance
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Chapter 15 427 Solutions to Problems 1. a. ortho -ethylphenol or 2-ethylphenol b. meta -bromochlorobenzene or 3-bromochlorobenzene c. meta -bromobenzaldehyde or 3-bromobenzaldehyde d. ortho -ethyltoluene or 2-ethyltoluene 2. CH 3 NH 2 a. CH 3 b. OH CH 3 c. CH 3 SO 3 H d. Cl 3. CH 3 a. NH 2 b. OH e. I HC g. NO 2 Cl NO 2 Br O 2 N O OH b. C d. Cl f. NH 2 h. Cl Cl N Br Cl Br 4. a. 1,3,5-tribromobenzene c. para- bromotoluene or 4-bromotoluene b. meta -nitrophenol or 3-nitrophenol d. ortho -dichlorobenzene or 1,2-dichlorobenzene 5. a. donates electrons by resonance and withdraws electrons inductively b. donates electrons by hyperconjugation c. withdraws electrons by resonance and withdraws electrons inductively d. donates electrons by resonance and withdraws electrons inductively e.
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21%20Ch15 - CHAPTER 15 Reactions of Substituted Benzenes...

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