Dolbier HW Solutions 317

Dolbier HW Solutions 317 - 411 ETHERS, EPOXIDES, AND...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
( h ) Under acidic conditions, substitution is favored at the carbon that can better support a positive charge. Aryl substituents stabilize carbocations, making the benzylic position the one that is attacked in an aryl substituted epoxide. ( i ) Tosylate esters undergo substitution with nucleophiles such as sodium butanethiolate. ( j ) Nucleophilic substitution proceeds with inversion of con f guration. 16.27 Oxidation of 4- tert -butylthiane yields two sulfoxides that are diastereomers of each other. Oxidation of both stereoisomeric sulfoxides yields the same sulfone. 16.28 Protonation of oxygen to form an alkyloxonium ion is followed by loss of water. The resulting car- bocation has a plane of symmetry and is achiral. Capture of the carbocation by methanol yields both enantiomers of 2-methoxy-2-phenylbutane. The product is racemic.
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

Ask a homework question - tutors are online