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Key-midterm-1-summer-2006

Key-midterm-1-summer-2006 - Méke Student Name Problem 1...

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Unformatted text preview: Méke Student Name: Problem 1 Complete the following reactions (don’t pay attention to the stereochemistry). (27 points) 1) N OHIH o \ 9 ‘9 a) M +\JCLU-O 2) :F'IHzc: Q>JWIQ C59 b) _____,... Chi—— 1)>fij\inpcm l c) CH3Li + CuBr —..—--)— (CH5) Cub-{t L6! 2, z. 2) H30+ ")\ J01)CH30',CH30H V |\ d) N02 + O --" //0 CNH o// e) —» <_ n O“ m OH ,pyrl me Q (9 u $( C§M M 0” Brz (traces ofP) t ow CN'Na+ ’0 n 0 ————»~ . or ——-» // J, \l DMF L\. x. O Mi he Student Name: A) The oc,[3—unsaturated carbonyl compound C is the result of an aldol condensation of two compounds A and B. What are the structures of A and B. (20 points) 0 <3” \“ 4- hi) @ Student Name: Pilfifk Provide all the reagents and intermediates needed for the following transformations (N0 mechanism needed). a) (10 points) dL. / e) 1 M 1 33.5960" cox/OM ‘9‘ (.0. 0 H.N——-< 09,- 9C0 SOL-04 Y x... EMF i 5' m b / ”#1:; ’7‘ 2 with! K 1 “:1” E/ :Dm E/ J" ‘9 H7 Hap b) (10 points) Student 1518.111an a L..— Complete the following reactions. (18 points) 2) H30+ 0 . u b) 0* 1) LiAIH4 in THF figure-Au / Br . c) 1-) MgIEther //j/\{\ a H‘ @ _____,_ g ,L 2) /& ,H+ 1) excess of CH3MgBr o 0H3 d) (74 J...» g cud o,\ 2)H3O+ Q .0 Lon Br H + 1) MglEther \O“ EtOHIH 6’ ————)-> ———-—)-» / 2) co 3) H3é+ g Q k @ Student Name: Problem 5 a) Provide all the reagents and intermediates needed for the following transformation , (Hint: try to find a retrosynthetic approach). All transformations were covered and elaborated during lectures. (10 points) a. L) Hf/HL“? fl»? 2:0 . ifiijiiif- bio/\xl/‘I‘u, Rube/H + .0 i\o / O HOWOH ——,———> H0 OQLFWQ ...
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