ProblemSet10 - CHEM 3570, FALL 2009 Problem Set 10 Chapters...

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CHEM 3570, FALL 2009 Problem Set 10 Chapters 8 & 9 and the rest of the universe……………… 1) Provide a detailed mechanism for the formation of A - E (show all intermediates). Which substitution/elimination mechanism is operative in the formation of each one of these products ( A - E )? What are the IUPAC names of B and D ? Br H + , H 2 O OH OH + + ++ AB CD E 2) The alkyl bromide shown can undergo an elimination reaction producing a mixture of A - D . Br H a H c H b H d + + + C D a) Imagine you could use a “magic” chiral base to selectively remove each one of the labeled hydrogen atoms ( a-d ). Match “surgically” precise removal of each labeled hydrogen atom with their resulting product (connect boxes with a line). H a H b H c H d A B C D b) Which product would you expect to be the major product if you used a very large (bulky) base for this reaction? By which mechanism is this reaction taking place?
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3) More synthesis!!! Provide a CHEM3570 state of the art synthetic route (reagents/conditions) for the following product.
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ProblemSet10 - CHEM 3570, FALL 2009 Problem Set 10 Chapters...

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