Exa2-09_NEW

Exa2-09_NEW - 1 (24 points). Devise syntheses for the...

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1 (24 points). Devise syntheses for the following molecules starting from alcohols containing no more than four carbon atoms and benzene. You may use any inorganic reagent and special organic reagents such as ether, carbon tetrachloride, pyridine, NBS, CH 2 N 2 , CF 3 COOOH and the sweat off the impressive brow of Ming the Merciless. Alas, you live on a planet that has no aluminum. Mechanisms are not necessary. H 3 C CH 2 CH 3 OH H 2 C CHCH 3 CH 3 (a) (b)
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1 . Your scheme involves the following reasonable final step: Br (CH 3 ) 3 CO 50 °C 1 Just for fun (and a few easy points) draw an arrow formalism for this step. However, you run the reaction in a hurry and, instead of 50 °C, you set temperature at 350 °C. The product is formed, but the label is no longer only where you want it. Explain (pictures and arrow formalisms, NOT just words) what happened. Note that the compounds shown are the only ones formed. Br
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Spring '10 term at NYU.

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Exa2-09_NEW - 1 (24 points). Devise syntheses for the...

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