Question

8. Predict the major product or products for the following reactions. Assume reagents are present in excess amounts unless otherwise indicated. Clearly depict any stereochemistry. "No Reaction is a possible answer. (4 points) each So, H2SO4 CH,CH,C1 AICI, NO Br2 FeBry OH 어 CI AICI, FeB

Answer 1

50₂H 503 H₂SO4 (sulfonation of benzene) CHally 5 + CH₂ CH3 CH₂ CH₂ CH₃ CH2 C CH₃ CH2 (1 CH₂ CH₂ CH₂ CH₂ AICI + си,су, exless ortho, Podt. in presence of excess CH₃ CH2 (1/AICI, multialkylation CH₂ CH₃ Waltz accure, -CH₂CH3 group is ortho, para directing, Ortno, patra group, 'Mechanism CH3 CH2 cl + hilla (Lewis acid) & OH₂-CH2-C1. -di-diz S + CH 3 CH 21 - dice Sation BY2 or complex Parafat. put HI CH2 CH3 D+ rearomatic NO2 NO2 FeBr, BO -Nog group is meta orienting group. Br-Br + Fe Brz + FeBr - Bo-Bo - Br-Br- de Bry NO2 7B2 Br-1 fr-feBay NO2 rearomatisation NO2 -Br Febr 1 Br o-complex OH AICZ o-acylation product angroppie orthohara ? orienting group. & Arclz Pet ci-AICI OH + Gi-All electrophile nocleophile C) OH 1. 2NaOH, 100°C 2) H ₂ OT (Aromatic nucleophilic substitute Horion) reaction Reaction proceeds via Carbanion intermediate stabilize by resonance, OH OH OH 04 1 Nucleophilic attack (-cih elminate. 6 (carbonion) 6 o

znLHS deluté HCl (eremmenson reduction) CH NBS Br hu Reaction proceeds via radical path. benzyl radical is more formed intermediate step stabilize. .by resonance, NO2 27 HCL -NH₂ Reduction of-NO2 group, C! No. realtion Diene Dienophile Diene is in S-trans form, which is not take part in (4+2) Cyclo - Addition reachionom ov, dieis alden reaction, *** گا۔ Br2 (let) FeBrz 7 -0- -BP electron rich electrophille enter at electronrich Phenyl ring electron deficiant due to I etbe and o -R effect of (-(-) Para Product (Major pat)