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Solution: Rank the SN1 reaction rates for the following compounds:iodomethane, 2-iodo-2-methylhexane, 1-iodo-2-methylhexane, 3-iodo-2-methylhexane

Problem

Rank the SN1 reaction rates for the following compounds:

iodomethane, 2-iodo-2-methylhexane, 1-iodo-2-methylhexane, 3-iodo-2-methylhexane

Solution

We’re being asked to rank the reaction rates of each compound for an SN1 reaction.


Recall that the SN1 reaction occurs in two steps:

(1) carbocation formation – the carbon-leaving group bond is broken

(2) nucleophilic attack – the nucleophile donates its electron to the positively-charged carbon (electrophile)



Hyperconjugation from additional R-groups stabilizes the carbocation. This means a more substituted alkyl halide will have a faster reaction rate.


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