5247

Explain the result, using structures and mechanisms.

5250

Compound A (C₅H₁₁N), was heated with excess methyl iodide, then treated with the base form of an anion exchange resin to give B (C₇H₁₇NO), a water soluble substance. When B was heated at 250°, a new product, C, distilled from the mixture, the structure of which is shown below. Deduce the structures of A and B.

CH₂=CHCH₂CH₂CH₂N(CH₃)₂

5264

Mescaline (C₁₁H₁₇NO₃), a hallucinogenic compound extracted from the flowering tops of a cactus found in the Southwestern United States, has the following ¹H-NMR spectrum: d (ppm) 1.0 (s, 2), 2.8 (m, 4), 3.8 (s, 9), and 6.8 (s, 2). Mescaline forms a salt A (C₁₁H₁₈NO₃Cl) with hydrogen chloride. Hofmann exhaustive methylation yields trimethylamine and compound B (C₁₁H₁₄O₃). Ozonolysis of B with reductive workup produces formaldehyde and an aldehyde C (C₁₀H₁₂O₄). Reaction of C with HI gives iodomethane and 3,4,5-trihydroxybenzaldehyde. From these data suggest the structural formula of mescaline. Show your reasoning.

5371

Coniine is one of the alkaloids isolated from hemlock, and purported to be that which poisoned Socrates. When optically active coniine undergoes Hofmann degradation, the major amine product (C₁₀H₂₁N) is optically active. Suggest a structure for this product.

coniine