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Unformatted text preview: Caroline Ho Nucleophilic Substitution Reactions of Alkyl Halides Purpose: Eleven halides were tested with two reagents for their reactivity. This experiment explores substitution reaction mechanisms and concepts. Discussion: Part 1: This is a very good scenario for Sn2 reactions because I- is a good nucleophile (good polarizability) and acetone is a polar aprotic solvent (does not hinder the nucleophile). Sn2 reactions favor mainly primary alkyl halides. Some secondary halides can react but usually at a slower rate. It is hard for tertiary halides to react by the Sn2 mechanism because the carbon atom linked to the leaving group is surrounded by alkyl groups on all sides, making it very hard for the nucleophile to attack. 1-bromopentane, 1-chloropentane, 1-bromo-2- methylpropane, and 1-bromo-2-2-dimethylpropane are primary halides however their reactions compared with each other are different. 1-bromopentane reacted the fastest because it has a Br leaving group as opposed to 1-chloropentanes Cl leaving group. Br- is a better leaving group than Cl- because its conjugate acid is stronger. 1-bromo-2-methylpropane, leaving group than Cl- because its conjugate acid is stronger....
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