Orgo 2 exam key 2 - Name Chem 308 Fall 2014 B Starting with...

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Unformatted text preview: Name Chem. 308, Fall 2014 B. Starting with the compound shown, and using any other organic compounds and reagents, devise a synthetic scheme leading to the product shown. Q 0' o \x/;‘\ to“ ‘LN\ O” r —* C) 2? $3 was “535:1 / /\ _""’ if .0" .9 3K: “(5H Z L) A r‘ O 3 ,d «125 Name Chem. 308, Fall 2014 TX. (12 points) A. Using only benzene, propanoyl chloride and ethylbromide as the only source of carbon, devise a synthetic sequence for the formation of the compound shown. Show distinct chemical reactions for each step in the sequence. Show the reactions needed to synthesize any organometallic or other special reagents. Indicate any specifically required solvents and reagents for all steps in the sequence. Put reagents and solvents above the arrow and any work up below the arrow. Once you write the structure of a compound you can designate it with a Roman numeral and use that in the rest of the sequence. Remember, count the carbons! The number of lines are sufficient for an efficient synthesis. Q Q t) A no: K/ (K: + V‘xck 'z)uL®-‘; { , A151 4’ {Efflék ‘4 N‘PVT‘K (fin 13,“ l... 7k _, m +t a? —x '1'1 ‘ A?“ #4 A /\P~V- 0'5) MLI l. 9% Q " 5—?“ ?k '1‘ -lk + t ,. _ ‘ , "Pa v? ...
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