HT2 ans - 2006 - Some Answers to Hour Examination #2,...

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Some Answers to Hour Examination #2, Chemistry 301X - 2006 1a and b. Here are the drawings: The two diastereomers are shown at the top and the products at the bottom. In these S N 2 reactions, the leaving group tosylate must be in the position as shown so that the obligatory displacement from the rear is possible. The Newman projections clearly show the gauche interaction in the left hand diastereomer that makes it difficult to achieve the proper orientation. H: H: O OTs H CH(CH 3 ) 2 (CH 3 ) 2 HC H H O OTs H H (CH 3 ) 2 HC CH(CH 3 ) 2 H O OTs H H (CH 3 ) 2 HC CH(CH 3 ) 2 O OTs H CH(CH 3 ) 2 (CH 3 ) 2 HC H (CH 3 ) 2 HC H O (CH 3 ) 2 HC H CH(CH 3 ) 2 H O (CH 3 ) 2 HC H OTs OTs O H H (CH 3 ) 2 HC CH(CH 3 ) 2 O H CH(CH 3 ) 2 (CH 3 ) 2 HC H
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1c. Protonation must be the first step - there simply isn t anything else to do. HC CH HO OH Z H 3 O + H 2 O HC CH HO OH 2 + H OH 2 + Now there are many possibilities: An internal S N 2 would ultimately produce an epoxide, but it has far fewer than six different carbons, so that reaasonable possibility must be
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HT2 ans - 2006 - Some Answers to Hour Examination #2,...

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