Organic Chemistry Practice Problems SN2 Reaction Practice Problems Solution: Rank the SN2 reaction rates for the following comp...

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Solution: Rank the SN2 reaction rates for the following compounds:2-bromo-3-methylbutane, bromomethane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane

Problem

Rank the SN2 reaction rates for the following compounds:

2-bromo-3-methylbutane, bromomethane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane

Solution

We’re being asked to rank the reaction rates of each compound for an SN2 reaction.


Recall that the SN2 reaction follows a backside attack from the nucleophile:



Steric interactions from additional R-groups makes it harder for the nucleophile to attack. This means a more substituted alkyl halide will have a slower reaction rate.


The relative rates for an SN2 reaction are: methyl (fastest) > 1˚ > 2˚ > 3˚ (slowest or no reaction)


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