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Experiment 10 discussion

Experiment 10 discussion - Experiment 10 Discussion...

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Experiment 10 Discussion NaI/Acetone: 1-bromopropane underwent an SN2 reaction because bromine is a good leaving group attached to a primary carbon, and it was introduced to a strong nucleophile (the iodine anion) in a polar aprotic solvent. 1-chloropropane also underwent an SN2 reaction. The reaction was slightly slower than with bromine because chlorine is a worse leaving group due to the fact that it is smaller and therefore less capable of holding a negative charge. 2-bromo and 3-bromopropane also underwent SN2 reactions in a similar fashion, however because they were both secondary carbons the reaction occurred slower because of steric hindrance of the nucleophile to a backside attack. 1-bromo-2-methylpropane also underwent SN2 in a similar fashion as 1-bromopropane, except the reaction was slower because the methyl group hindered backside attack. 2-chloro-2-methylpropane underwent an SN1 reaction. The LG was on a tertiary carbon, so although the solvent wasn’t ideal the iodine attacked the carbocation and formed product. 1-bromo-2,2-dimethyl propane proceeds via the SN2 mechanism, however it is much slower due to the two methyl groups hinder the backside attack.
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