Question

15) === BONUS (20 pts) === Novocaine (C13H20N202) is a common local anesthetic used in medicine and dentistry. If Novocaine is refluxed with aqueous KOH, an insoluble liquid X (C6H15NO) separates from the aqueous medium. After extraction of X with organic solvent, the remaining aqueous phase is acidified yielding a crystalline solid Y (C7H7NO2). X is identical with the compound obtained when diethylamine, (CH3CH2)2NH, is reacted with ethylene oxide and exhibits the 1H NMR seen below. L6H Y exhibits the IR and 1 H NMR spectra that follow. 3461 3303 (a) Determine the structures of X,Y & Novocaine. For full credit, assign all the HNMR peaks in the 2 HNMR spectra shown above and the bond stretches in the IR spectrum. (b) Write structural equations for all reactions that occur in this analysis. Use the back of this page to answer this question.

Answer 1

*21 25 3S HOH-CH H 0, t13H 25 SH mz 2:r PyZM 2 dindhylamine edhano! myzH25GH もB10=6H #88 y 4 Aniue Loganicaa 6 2H +81d-2H 34G1-N-H stretehing 3RO3-0-H staateking of akexy lie a id 20 C-H skele bing of Gnjugate alkwe(Arondig Gesc shele bing of akorylte a cid ctedchtng of Gjugaked alkeueftaomatie Novo Caine c CH3 xglux RO-C-CN Aaneaus layos Caciolsied &aysblig Ho-cy STCOene aee