Dolbier HW Solutions 201

Dolbier HW Solutions 201 - 195 NUCLEOPHILIC SUBSTITUTION...

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

View Full Document Right Arrow Icon
8.27 This reaction has been reported in the chemical literature and proceeds as shown (91% yield): Notice that the con f guration of the product is the same as the con f guration of the reactant. This is because the stereogenic center is not involved in the reaction. When we say that S N 2 reactions pro- ceed with inversion of con f guration we refer only to the carbon at which substitution takes place, not a stereogenic center elsewhere in the molecule. \ 8.28 ( a ) The starting material incorporates both a primary chloride and a secondary chloride. The nucleophile (iodide) attacks the less hindered primary position. ( b ) Nucleophilic substitution of the f rst bromide by sulfur occurs in the usual way. The product of this step cyclizes by way of an intramolecular nucleophilic substitution. ( c ) The nucleophile is a dianion (S 2 2 ). Two nucleophilic substitution reactions take place; the sec- ond of the two leads to intramolecular cyclization.
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 09/26/2011 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