CHEM264 Lecture Notes - Lecture 16: Stereospecificity, Meta-Chloroperoxybenzoic Acid, Steric Effects

• School: University of Waterloo
• Department: Chemistry
• Course: CHEM264
• Professor: Mike Chong

Document Summary

O(cid:271)e(cid:455)s ma(cid:396)ko(cid:448)(cid:374)iko(cid:448)"s rule fo(cid:396) h additio(cid:374), x goes o(cid:374)to (cid:373)o(cid:396)e su(cid:271) c. Rearrangement will occur to produce most stable carbocation (3>2>1>methyl) Stereoisomers will form due to the fact that cc double bond is sp2 hybridized and is flat (can attack from bottom or top) Acid catalyzed addition of water (alkene + acid + water -> alch) A(cid:272)id (cid:894)h+(cid:895) o(cid:271)e(cid:455)s ma(cid:396)ko(cid:448)(cid:374)iko(cid:448)"s rule, oh atta(cid:272)ks (cid:373)o(cid:396)e su(cid:271) c. Rearrangements will occur to produce most stable carbocation. In cis compounds, double bond will temporarily break to allow molecule to rotate and form trans to minimize steric hindrance. Reverse- dehydration (alch + acid-> alkene + hx -> alkane) Acid rips oh and closest h to oh off of alch and forms a double bond. Hx then reacts with double bond to form alkane. Oxymercuration-demercuration (alkene+ hg(oac)2 + water -> alch with hg + bh4 -> alch) Alkene reacts with hg(oac)2 to form 3 member ring with c-hg-c (high strain)