C C Chapter 8 and 9 review -- the reagents Nolta 2009 E / N H CH 3 H 3 C Ph Electrophilic addition Reactions - the General Scheme E = Electrophile (something lacking electrons/positive in nature) it is attacked by the pi electrons in the initial step in the reaction, the pi electrons form a new bond from the hinge carbon to the electrophile. N = Nucleophile (negative in nature) provides electrons for a new bond to one of the carbons of the pi bond; this occurs in a different step or at the same time the electrophile is attacked. The timing impacts the stereoselection (or not) of the reaction. R e a g e n t s R e g i o s e l e c t i v i t y S t e r e o s e l e c t i v i t y P r o d u c t ( s ) H / OH H 3 O + or H 2 O/H 2 SO 4 Markovnikov C+ -- not stereoselective OH / OH KMnO 4 or OsO 4 None syn OH C C CH 3 H H 3 C Ph H + enantiomer H / OH 1) BH 3 (9-BBN) 2) NaOH, H 2 O 2 , H 2 O "Anti-Markovnikov" syn X 2 None anti + enantiomer Note a s t a g g e r e d conformer is drawn
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This note was uploaded on 01/28/2011 for the course CHEM 215 taught by Professor Koreeda during the Spring '07 term at University of Michigan.