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10. (12 pts) Compound A (CeHsNO, one degree of unsaturation) produces ammonia gas uporn heating with NaOH/M20. When the resulting solution is acidified and extracted wi e compound B is isolated. Compound C is formed when compound B is heated methanol. Reduction of compound C with LiAlH4, tollowed by acid workup yields me and compound D (still containing 6 carbons). The proton and carbon NMR data for b can be found on the following page. with acidic (a) What are the structures of compounds A. B, C, and D? Show these compounds within the synthetic route described above (no mechanisms). (b) Label the BOTH the proton and carbon NMR to reflect all of the signals in compound D. Redraw the structure on the NMR spectra and label atoms and peaks using lowercase a, b, c, d, etc
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Answer #1

Rnida wri th Ceo H CH-@g-cSe-o凵 CH.3 ーー 3 ㄈㄩas 3-y 13c (c,e) d MOhave any imteaction 2S as as S 0 e (a,b) a. 3.5 3.4

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