With phosphorus pentaehloride

Phosphorus pentaehloride acts on selenium dioxide with the formation of the tetrachloride, whilst phosphorus trichloride yields brown amorphous selenium in these reactions phosphorus oxychloride is also formed. 

Examine a small amount of phosphorus pentaehloride, about 1 gram. (1) Describe its appearance. Determine whether or not it will hydrolyze. (2) What did you do and with what results (3) What do you conclude (4) What property of phosphorus might lead you to expect this action ... 

Constitution. Pelletierine behaves as a secondary amine and the oxygen atom of the alkaloid is present in the form of an aldehyde group, since the base yields an oxime, convertible by the action of phosphorus pentaehloride into a nitrile, b.p. 104-6°/15 mm., which is hydrolysed by caustic potash in alcohol to an acid, the ethyl ester of which is LSffler and Kaim s ethyl /S-2-piperidylpropionate. Pelletierine is not directly oxidisable to this acid. It also yields a liquid hydrazone, b.p. 150°/20 mm., which with sodium in alcohol at 156-70° reduces to df-coniine. These reactions are explained by the following formulas, in which pelletierine is represented as -2-piperidylpropionaldehyde. 

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