Final%20AK%20(F'09)

Final%20AK%20(F'09) - Chemistry 233 Organic I Due April 29,...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
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)
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
B ) Below, please draw both A and B in their two chair forms and label their substituents as either equatorial ( eq ) or axial ( ax ).
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 09/18/2011 for the course CHEM 233 taught by Professor Shi during the Fall '08 term at WVU.

Page1 / 11

Final%20AK%20(F'09) - Chemistry 233 Organic I Due April 29,...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online