Solved: The red fox (Vulpes vulpes) uses a chemical communication system based on scent

Chapter 18, Problem 18.38

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The red fox (Vulpes vulpes) uses a chemical communication system based on scent marks in urine. One component of fox urine is a sulfide whose mass spectrum has M1 5 116. IR spectroscopy shows an intense band at 890 cm21, and 1H NMR spectroscopy reveals the following peaks: 1.74 d (3 H, singlet); 2.11 d (3 H, singlet); 2.27 d (2 H, triplet, J 5 4.2 Hz); 2.57 d (2 H, triplet, J 5 4.2 Hz); 4.73 d (2 H, broad) Propose a structure consistent with these data. [Note: (CH3)2S absorbs at 2.1 d.]

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