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CHM 2220 Organic Chemistry 2220 Winter Term 2010 Problem Set #1 of 5 20 PTS Instructor: Prof. Andreana
 

Summary: CHM 2220 Organic Chemistry 2220 Winter Term 2010
Problem Set #1 of 5 20 PTS Instructor: Prof. Andreana
Room #: DRY 0146
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1) The loss of absolute stereochemical information (but retention of relative stereochemistry) occurs
in a reaction that is illustrated below. Please provide a mechanism that includes a transition state
(?) for the reaction illustrated below (It should explain "retention" of stereochemistry). Also, explain
what absolute and relative stereochemistry means including depictions to support both. 10 PTS
The oxonium ion intermediate that is formed in this next transformation is delocalized and achiral. If
a single enantiomer of the starting material is used, racemic product is formed through the achiral
intermediate. Attack at one carbon atom gives on enantiomer; attack at the other gives the mirror
image. Please provide a mechanism that includes a transition state (?) for the reaction illustrated
below.
When the reaction is carried out in ethanol (below), the intermediated is "trapped" revealing a stable
orthoester. Please provide a mechanism that includes a transition state (?) for the reaction
illustrated below.
OTs

  

Source: Andreana, Peter R. - Department of Chemistry, Wayne State University

 

Collections: Chemistry