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Organic Chemistry — Ch 7.pdfPage 243 of 612
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CHAPTER 7 · Nucleophilic Substitution243
7.3  The SN2 reaction

In the SN2 pathway the nucleophile attacks as the leaving group departs, in a single concerted step. The transition state is crowded, so the reaction favours methyl and primary carbons and proceeds with inversion of configuration — the Walden inversion.

Figure 7.4 Backside attack. The nucleophile approaches 180° from the leaving group; bond-making and bond-breaking happen at once.

The SN1 pathway is stepwise: the leaving group departs first to form a planar carbocation, which the nucleophile attacks from either face, giving a racemic mixture. Tertiary substrates and polar protic solvents favour it.

Key idea SN2: rate = k[RX][Nu−], one step.  SN1: rate = k[RX], carbocation first.

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