CHEM 353 Quiz: N09-353-Electrophilic+Aromatic+Substitution
2 Aug 2014
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Previous material that is important to know: (cid:120) concept of aromaticity (cid:120) drawing (and ranking) resonance structures (cid:120) carbocation stability. Introduction: (cid:120) apply your understanding of eas to naphthalene and heterocycles (14. 8) (cid:120) Representative electrophilic aromatic substitution (eas) reactions of benzene: (cid:120) the general reaction scheme is outlined below: Nitration of benzene: (cid:120) electrophile is the nitronium ion (no2. Ashley causton 2014 (cid:120) step 1: attack of electrophile on (cid:83)-electron system of aromatic ring (cid:120) step 2: loss of a proton from the carbocation intermediate. Sulfonation of benzene: (cid:120) electrophile is sulfur trioxide (so3) Ashley causton 2014 (cid:120) electrophile is a lewis acid-lewis base complex between febr3 and br2 this complex is more electrophilic than br2 alone. What is the electrophile in the above reaction ? (cid:120) a related reaction involves alkylation with double bonds. In the example below, cyclohexene is protonated by sulfuric acid, giving cyclohexyl cation which attacks the benzene ring.
