0244Pb2an-10.cwk (WP)

0244Pb2an-10.cwk (WP) - produces a more stable tertiary...

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

View Full Document Right Arrow Icon
Answer to Problem 2, Chemistry 0244-2010 The words “first order” should signal an S N 1 reaction. Compound 1 ionizes to give a resonance-stabilized allylic cation. Addition of water at the two positions bearing the positive charge gives a pair of alcohols. (CH 3 ) 3 C OTs S N 1 (CH 3 ) 3 C (CH 3 ) 3 C H 2 O (CH 3 ) 3 C (CH 3 ) 3 C + OH 2 OH 2 (CH 3 ) 3 C OH 1 (CH 3 ) 3 C OH The two alcohols Compound 2 ionizes to give a secondary carbocation, but a hydride shift not only
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: produces a more stable tertiary carbocation, but that cation is identical to that formed from 1 . Of course the same two alcohols must be formed and they must be formed in the same ratio as from 1 . (CH 3 ) 3 C (CH 3 ) 3 C (CH 3 ) 3 C OTs (CH 3 ) 3 C H...
View Full Document

Ask a homework question - tutors are online