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322bs05_sample3_2

322bs05_sample3_2 - Spring 2004 GV’ZOh W Organic...

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Unformatted text preview: Spring 2004 GV’ZOh W Organic Chemistry 322bL March 24, 2004 3rd Hour Exam / Name Initial of Last Name Total Zinc/[v 1. Write the products of the following reactions. (30 pts. ) THF ‘L ”H )Ph- SeBr &59 -pA 3) H202 0 II i? e. Ph-C—CH3 + CH2: 0 + HNEt2 —HCJ—> Pk..c «CHECMI—M a?” a. ”2/0) Afiw/vfi'izLA/Umf fl 75:620 f. Etc—(ii j: 1W, W COL” 1' fl f” OE‘ 2) di|ute H9 A 1:2 3:: Na (”LC/Mew”); if if 1) NaOEt l _ - _ _ _ (9 9. Ph CH2 C GB + BO 0 OEt 2) H30 fi? P4010 it 3 2' 2" 2_———> ""l/ C "C ”CE CHQCH CH CNH kgd’ (Mb 0 V14) V11 g > H o g > W 2. CHz—CN —2--> CH2-C\ G H NH2 0 CF3 F3 Write a reasonable mechanism for the acid catalyzed hydrolysis of a itrile to the corresponding amide. Use curved arrows to show electron pair movgtentfls pts.) ® ‘— " -——' 0" GLEN/31M ————~ 933% H --> Cf‘” H 0‘? cg 0% ”LOW cg We v1 0/” 3- The reaction below is an example of the Darzens reaction. in e PE>=0 + Cl-CH2-0020H3 + Na? OCH3 H COQCHa + NaCl+CH30H 0 Outline a reasonable mechanism for this reaction. Use curved arrows and write the structure of intermediates. (10 pts.) C _ C\ZCH-Coz% ——4 Cl’ml/al '0”C W11 H 447; “ 4 ”’6 / 4e W14 s" M14 sznfluw‘%;bwa Fir/6|» 4. Selecting from among diethylmalonate (CH2(COZE1) 2), urea, bromobenzene, ethyl phenylacetate (Ph-CHz-COgEt). diethyl carbonate and ethyl bromide as the sole product carbon sources, outline a synthesis of phenobarbital.(15 PtS-l Et Ph 4014 X. lot/c a“! 5. Selecting from among 1 ,3-dibromopropane, 1,4-dibromobutane, and diethyl malonate l? [CH2(CogEt)2] and ethyl acetoacetate (CHa-C-CHg-COZEt) as the sole product carbon sources, outline a synthesis of cyclobutane carboxylic acid. D\ r l .t Vwé'f (Maori 5‘6)» _C______,___, Cam 0056}; (Z) Kr (Ce/2J3 gr ”I" I 1 ”405—6 (15 ptS-l COZH 6. lpé/w‘ pm..wa WK coin/ff Write a reasonable mechanism for the conversion of A to B. Be certain to write the o V m. structures of the intermediates involved. Only the intermediates will be graded. ‘ (15 pts.) (9 . msMgBr J2 ” a EtZO O (2} O 2) KOH / H20 A are L L 53 : ”“5550? ...
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