B joc provide the product from the reaction of

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B) ( JOC , 2009 , 74 , 545) Provide the product from the reaction of Moledule A. O O O O O O 1) catalytic NaOCH 3 , excess CH 3 OH CH 2 Br 2) 2 NaH, 2 excess H 2 O, TsOH A Molecule A would be sensitive to acid aqueous conditions. Fill in the fully hydrolized product below. 5 5 4 4 10 H H H O O O O O O A H H H
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IV. (24 points) Name:_________KEY_____________________ W09_215_E2_p4 A) J. Chem. Educ. 2007 , 84 , 475. i) Provide the two reactants Na 2 CO 3 N O + OH NO 2 When the product is heated, dehydration occurs. N O OH NO 2 N O NO 2 Na 2 CO 3 H 2 O, heat + H 2 O ii) Show the mechanism of the dehydration in base. Show both the formation of the dehydration product and water. You may use B - for the base and HB for its conjugate acid. N O OH NO 2 B - N O NO 2 + H 2 O (aq) (s) (l) room temperature 6 10 B) ( Tettrahdron Lett. 2009 , 50 , 111.) There are two different ketone enolates that can form via deprotonation of the starting material under these reaction conditions, one is produced more rapidly (the kinetic product), the other is more thermodynamically stable. N CH 3 O O CH 3 O NaOH C 13 H 13 NO Final product thermodynamic enolate kinetic enolate Using NaOH, you might expect to see selective formation of one of the enolates. The final product comes from the use of the unexcepected enolate in an intramolecular reaction This is due to a more stable ring size in the final product. Use the molecular formula of the product to guide you through the remainder of the reaction.
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