Chem3AL-Lab7 - Nucleophilic Substitution Reactions of Alkyl...

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Nucleophilic Substitution Reactions of Alkyl Halides Three factors affecting the type of reactions between molecules, S N 1 or S N 2, are the solvent, the nature of the leaving group, and the structure of the substrates. In this lab two solvents were used: acetone and ethanol. Acetone is a polar aprotic compound, which are better suited for S N 2 reactions. Ethanol is a polar protic compound, which are better suited for S N 1 reactions. The leaving groups of the subtrates in the lab were bromine and chlorine. Chlorine is more electronegative than bromine making it a better nucleophile, meaning it has strong interactions with the electrophiles. This stronger attraction makes chlorine a worse leaving group than bromine and thus requires more energy to pull it off of the electrophile. The structures of the subtrates themselves, also affect the rate of reaction in S N 2. The carbon attached to the leaving group is called the α -carbon and the carbons attached to the α -carbon are called the β -carbons. Branching on the β -carbons inhibits the ability for S N 2 reactions to proceed because of increased
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This note was uploaded on 02/02/2009 for the course CHEM 3AL taught by Professor Li during the Summer '08 term at University of California, Berkeley.

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Chem3AL-Lab7 - Nucleophilic Substitution Reactions of Alkyl...

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