Around 1912, Swiss chemist Richard Willsttter (who subsequently was awarded the 1915

Chapter 23, Problem 23.77

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Around 1912, Swiss chemist Richard Willsttter (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. N(CH3)2 N(CH3)2 N(CH3)2 (CH3)2N A C Identify the two hydrocarbons B and D, and explain their very different behavior toward Br2. (Willsttter concluded from these observations that compound D could not be an alkene.)

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