Question

10. Furan, an aromatic heterocycle, is capable of undergoing electrophilic aromatic substitution. When furan is treated with an acid chloride in the presence of a Lewis acid, Friedel-Crafts acylation occurs in which the electrophile is installed exclusively at the C2 position. Provide a detailed, stepwise mechanism the transformation above. Use the curved arrow formalism to show the flow of electrons. Show all lone pairs, formal charges, and pertinent resonance structures. Explain why this reaction occurs at the C2 position, rather than the C3 position. Provide any important structures to illustrate your explanation.

PLEASE ANSWER ALL A-G, will give thumbs up!! FOR A, just need explanation why reaction occurs at C2 position rather than C3, already have mechanism drawn...   

PLEASE EXPLAIN OR AT LEAST JUST ANSWER ALL ASAP, BEFORE TOMORROW!!

Answer 1

Il Alllz This reaction occurs at the Co position, rather than the Cz position لا 27 FO electrophile 3-position > When [o attack at 2-position, 3-resonating structure possible but when attack at 3-position, only 2-resonating structure possible. more resonating stucture more stable. That means prefessed position for the seco attack is position-2 Mechanism: Step-s. The acyl halide reacts with the Lewis acid to form a complex. :00 Che di Alls (H&C-ARCH Step-2 Loss of halide to the lewis acid form electrophillic acylium ion CHS + -ABU step3 | 7) (show step) step-3 Ha

t Hills Xorna HOLX. isoprene > It gives electrophillic addition reaction - IY ☺ V I pH electrophile la attack Carbocation (Slow step) intermediate co attack - - - Cat Hy sou 1,0 + HN HO Hydrolysis : 2-I.