CH232_1996SPRING_EXAM3__[0]

CH232_1996SPRING_EXAM3__[0] - 2 / dilute HCI 4.Provide...

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Organic Chemistry CH232 M a y 1 996 Third Exam inat ion 1-. Show how one could synthesize the following compounds ,starting with acetic acid and any other organic or inorganic reagent you may need : (a) H 2 NCH 2 CO 2 H ( d ) BrCH 2 CO 2 CH 2 CH 3 (b) NCCH 2 CO 2 H (c)HO 2 CH 2 CO 2 H 2. Mescaline , a hallucinogenic am ine obtained from the peyote cactus, has been synthesized in two steps from 3,4,5-trimethoxybenzyl bromide . The first step is ( 10 J n u c l e o p h i f i c substitution by sodium cyanide . The second step is lithium aluminum hydride reduction . Write the structure of mescaline . 3.Write the structure of the expected product formed when benzylamine reacts with / . e
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Unformatted text preview: 2 / dilute HCI 4.Provide structures for the following ; (a) 2-ethyl-1-butanamine (b) N-ethyl-2-butanamine (c) tetraethylammonium hydroxide . 5. When Compound A is heated two isomeric products are formed . Write each /o) s t r u c t u r e . COjH CO2H Compound A [ _\ 6 . N-Nitroso amines are stabilized by electron delocalization. Write the two most stable resonance forms for N-nitrosodimethylamine . (CH 3 ) 2 N-N=O: i ,-\ 7.Startin g with ammonia and any other reagents you may need , synthesize \ ' N-n i t r o s o d i m e t h y l a m i n e . EVAH A TAERG REMMUS...
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