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Reactions_to_Review_CHM2120 - trans diol D i o l f o r m a...

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CHM 2120 REACTIONS TO REVIEW CH 3 1. B H 3 2. H 2 O 2 ,NaOH CH 3 H H H O H The reaction is regioselective: the anti-Markovnikov product is major. The reaction is stereospecific: the H and O H add exclusively in syn fashion. CH 3 H H y d r o b o r a t i o n - o x i d a t i o n Note: the numbers (1. and 2.) denote that the reaction occurs in 2 separate steps. These reagents are not mixed together all at once. KMnO 4 ,NaOH OR OsO 4 ,NMO CH 3 H OH OH Thereact ionisstereospec i f
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Unformatted text preview: trans diol? D i o l f o r m a t i o n : O z o n o l y s i s : CH 3 H 1. O 3 2. PPh 3 OR SMe 2 CH 3 H O O H 3 C O H O ≡ Note: two carbonyls in a molecule is a clue that the molecule could have been synthesized from an ozonolysis reaction H y d r o g e n a t i o n : R H C C H R H 2 , Pd/C R H 2 C C H 2 R R R R R R R H 2 , Pd/C R H 2 C C H 2 R H 2 , Pd/C BaSO 4 or CaCO 3 R C C R H H R C C R H H Li NH 3...
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