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20.2 Outline a procedure for separating a mixture

20.2 Outline a procedure for separating a mixture

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H 3CH 2C<br />

NH 2<br />

CH 2CH 3<br />

20.42 Compound B, an isomer of (Problem 20.41), is also soluble in dilute HCl. The IR<br />

spectrum of B shows no bands in the 3300-3500 cm -1 region. The broadband proton-decoupled<br />

13<br />

C spectrum of B is given in Fig. 20.9. Propose a structure <strong>for</strong> B.<br />

Answer:<br />

H 3CH 2C<br />

N<br />

CH 2CH 3<br />

20.43 Compound C (C9H11NO) gives a positive Tollens’ test and is soluble in dilute HCl. The IR<br />

spectrum of C shows a strong band near 1695 cm -1 but shows no bands in the 3300-3500 cm -1<br />

region. The broadband proton-decoupled 13 C NMR spectrum of C is shown in Fig. 20.9. Propose a<br />

structure <strong>for</strong> C.<br />

Answer:<br />

CHO<br />

N<br />

H3C CH3 20.44 <strong>Outline</strong> a synthesis of acetylcholine iodide using as organic starting materials:<br />

dimethylamine, oxirane, and acetyl chloride.

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