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fall-07-zimmerman-q7-key - Z:MWM=/l Organic Chemistry 345 e...

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Unformatted text preview: Z:MWM=/l Organic Chemistry 345 e Spring 2007 Quiz 7a Name (Please Print, Clearly) Give the products of synthesis as isolated after workup. E”) Pyn'olldme Me-I A (Mg 2 Phthalimide -QH} 4',“ch ”3,4314 ) 1) KOH EtOH\-{1:/)Md 2) n-Butyl Iodide - k 3) Ph-(f-NH-Ph Pk‘QH‘ NH p l LiAIH4, EtZO 4) PhZC-CPhZ f» Pk'C—Q “it I \ H ‘5 HO OH Ph-C-NH L— NH» 5) n 2 NaOCI P O + _ 6) Ph-C—N=N=N IDL’NWL‘: 0 H benzene A O 14 ,‘l er C " b 7 N ——I- " h ) Ph =0: 0 EtOH ‘ P o 8) Which is least basic: Cyclohexylamine, Aniline. p—Nitroaniline, ? ill-”Nth'afiit )5". Which is most basic of the above three ? C1 06°h9'x1l M V‘ C- 9) Carefuly write out the resonance structure responsible for the 1000 basicity of p—cyanoaniline. As usual put in all unshared electrons and formal chargesl 2 :6 fl) r+ a“ If you treat a racemic amine with an optically active acid. what will result is a set of OQAS‘PWE’MV 3' 10) (enantiomers, diastereomers) E ntio rs have 3‘ M (the same different) physical properties while diastereomers have Ja M‘ (the same ,different) physical properties 11) How do you explain the difference In basicity of amides compared with amines? Make clear which is more basic and also include any resonance structures need to explain A) De/ochzil‘iMof ‘{ Wish 101ml“ mi 10.1?on walks H’lch r prfiamhm m (2&ch Mrdflfl 93355“; $3:in 170“ (”8C5 “flu. $1.804ch energy R"O-"" Bey/N (MSM¢%UIUmV{t-3 9:0 ”amt/ML denim 49%er M widow ...
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