Solution B prepared by adding potassium methoxide to acetic acid rapidly undergoes anacid–base reaction:Thus the major base present is not methoxide but acetate. Methyl iodide therefore reacts with acetateanion in solution B to give methyl acetate.8.42Alkyl chlorides arise by the reaction sequence:The reaction proceeds to form the alkyl p-toluenesulfonate as expected, but the chloride anionformed in this step subsequently acts as a nucleophile and displaces p-toluenesulfonate fromRCH2OTs.8.43Iodide ion is both a better nucleophile than cyanide and a better leaving group than bromide. Thetwo reactions shown are therefore faster than the reaction of cyclopentyl bromide with sodiumcyanide alone.8.44–8.47Solutions to molecular modeling exercises are not provided in this Study Guide and Solutions Man-ual.You should use Learning By Modeling
This is the end of the preview. Sign up
access the rest of the document.
This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.