Around 1912, Swiss chemist Richard Willsttter (who subsequently was awarded the 1915 Nobel Prize in Chemistry) treated

Around 1912, Swiss chemist Richard Willstätter (who subsequently was awarded the 1915 Nobel Prize in Chemistry) treated diamine A with methyl iodide and then with Ag₂O and heat, whereupon a hydrocarbon B, C₈H₈, distilled from the reaction mixture. Compound B reacted rapidly with Br₂ under mild conditions. Treatment of compound C in the same way gave a hydrocarbon D, C₆H₆, which did not react with Br₂.

Identify the two hydrocarbons B and D, and explain their very different behavior toward Br₂. (Willstätter concluded from these observations that compound D could not be an alkene.)

Transcribed Image Text:

(CH3)₂N A -N(CH3)2 N(CH3)2 N(CH3)2 с