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Dolbier HW Solutions 201 - 195 NUCLEOPHILIC SUBSTITUTION...

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8.27 This reaction has been reported in the chemical literature and proceeds as shown (91% yield): Notice that the con fi guration of the product is the same as the con fi 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 fi 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 fi 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 ). Two nucleophilic substitution reactions take place; the sec- ond of the two leads to intramolecular cyclization.
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