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Final%20AK%20(F'09)

Final%20AK%20(F'09) - Chemistry 233 Organic I Due George A...

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Chemistry 233 Due April 29, 2010 Organic I George A. O’Doherty Exam #3 Name: ID# (Please also put your name and ID# on the last page) There is a total of 200 points for this exam. [I] ( 55 points ) i) When (5 S )-5- tert -butyl-1-methylcyclohex-1-ene reacts with Br 2 in water (Br 2 /H 2 O) it forms two diastereomeric bromohydrins A and B . Where A is the (1 R , 2 R , 5 S )-isomer and B is the (1 S , 2 S , 5 S )-isomer. ii) When bromohydrin A is treated with NaH it rapidly closes to form product C . Similarly, when B is treated with NaH it closes to form product D (see reaction below). iii) An identically mixture of products C and D is also formed when (5 S )-5- tert -butyl-1-methylcyclohex-1-ene reacts with mCPBA. iv) Use these details to help you answer the questions below ( A - E ). Br 2 /H 2 O + A B NaH D C NaH OH Br OH Br (5 S ) (5 S ) (1 S ) (2 S ) (1 R ) (2 R ) O O (5 S ) (5 S ) (2 R ) (1 S ) (1 R ) (2 S ) A ) In the boxes above , draw the structure of the products A , B , C and D (please include stereochemistry). (20 points)
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B ) Below, please draw both A and B in their two chair forms and label their substituents as either equatorial ( eq ) or axial ( ax ). Thus the conformer of A
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