Question

2. (12 points, 6 points each) Give the arrow pushing mechanism for To of the following reactions. Draw the resonance structures of the intermediate. You MUST include the mechanism for the formation of the electrophile for electrophilic substitution reactions. Do not combine steps and be sure to show arrows and charges for all steps. Gie Twoyo.coc.c.m.m.ci.e groded..ay are wotcleurly marked hwiti only gade wor A. HNO, H,So B. 1. AICI 2. H2o

Answer 1

Solution: HNO3 No H2504 Mechanism: step. 1 -&_ w@so, y = 23 -85 ON=0 nitronium ion. step-2 Joane OEN 8 NOR o tego so - E] + HO SO3H step-y: Nitronium ion generation is HNO₃ / H₂504 step-2: Aromatic electrophilic substitution reaction to give desired product. # 1. Alcl₂ 2.H₂O

step-1: erry Rd, tel-Alla Step-2:- on-ep-1- Step-1: Reaction of acid chloride with Aldo to generate electrophile. This a Friedel - crafts acylation reaction. step-2: In situ seuction of a benzene ring to give desire product This is aromatic electrophilic substitution reactions. NO2 ON Nao CH 2 CH3 .NOR O " No O CHECK PRET ""> heat Mechanismi e No2 T & CH₂ CH₂ SON Are No 1 ton 12 CH₂ L E

NO NO2 NO2 Sign) - Benzene ring contain two electron with drawing nitro group ortho and para to fluorine. Thus it under goes aromatic nucleophilic sub- stitution reaction to give desired product NaNH2 NH3 NH2 Mechanism: F This reaction under goes aromatic nucleophilic substitution reaction. Fluorine is good for SNAr because of its high electronegativity it pulls electron towards itself and make its adjust carbon more more electrophilic. The chances of formation of by product is very less.