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1-bromo-3-methylbutane vs 1-bromo-3-methyl-2-butene vs 1-bromo-2,2=dimethylpropane Which compound reacts fastest in respect to SN2. Which is slowest?

1-bromo-3-methylbutane vs 1-bromo-3-methyl-2-butene vs 1-bromo-2,2=dimethylpropane Which compound reacts fastest in respect to SN2. Which is slowest?

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Answer #1

As the steric on the carbon having the leaving group increases the rate at which SN2 reaction occurs decreases so the structures are as shown. Though the alkyl bromide is not crowded the sterics are still important so 1-bromo-2,2-dimethylpropane is the slowest and 1-bromo-3-methylbutane is the fastest the olefin will make the compound crowded as it does not allow any bond rotation.

Br 1-bromo-3-me thyibutane 1-bromo-3-methyl-2 bute ne 1-bromo-2,2-dime thyipmopane 1-bromo-3-me thvlbutane Fastest Intermedia

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