Skytanthine is a monoterpene alkaloid with the following properties. Analysis: C₁₁H₂₁N. ¹H NMR: two CH₃ doublets (J = 7 Hz) at δ = 1.20 and 1.33 ppm; one CH₃ singlet at δ = 2.32 ppm; other hydrogens give rise to broad signals at δ = 1.3 – 2.7 ppm. IR: no bands ≥ 3100 cm^-1. Deduce the structures of skytanthine and degradation products A, B, and C from this information.

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CI 1. -CO,.H, CH.CI, 1. CHẠI 2. Ag.O, H,O 3. Д 1. 0,, CH,CI, 2. Zn, H.O 2. КОН, Н.О Skytanthine C1H23N → CH,=0 + CH2NO A в IR: i = 1646 cm- IR: = 1715 cm- Careful oxidation CH;COOH + C,H19NO CH3 C IR: i = 3620 cm-! ČH,N(CH3)2 IR: i = 1745 cm-