Question

Need help with problem 1 - I am not quite sure how to draw the conjugate acid for both the C2 and C3 positions.

Can someone please check my protanation at the C2 and C3 positions and my resonance structures?

1. Consider the structure of indole shown below. Indole prefers to protonate at Cs rather than Ca under strongly acidic conditions. Draw the conjugate acid for both the C2 and Cs positions, and rationalize this selectivity with the use of resonance for each conjugate acid. ???" 2 (a) Protonation at C2 and two additional resonance structures. +H (b) Protonation at Cs and an additional resonance structure. E+ (c) Rationalize why protonation at Cs is better. DCJT Roys h rotanatin at C3 1as fewer AT lud by ?.TR o(rf ,J the AROMATItify RrN e Ca' std, l: once fons Provide syntheses for the following transformations. Be sure to show all reagents and intermediate nroducts 2,

Answer 1

け Base nid C. Acid ba Cs latban lt Caye nud +1aye th t