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Sn2 Reactions

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Arrange the following compounds in order of increasing reactivity in an Sn2 reaction. First present the structure of the compounds and then rank them with clear explanations.

bromocyclohexane; 1-bromo-1-methylcyclohexane; 1-bromomethylcyclohexane; (1-bromoethyl)cyclohexane; and 1-bromo-2-cyclohexylethane

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Solution Preview

The structures of the five compounds are drawn in the attached file.
They are numbered from 1 to 5:

1) bromocyclohexane ---bromine is attached to a secondary C
2) 1-bromo-1-methylcyclohexane ---bromine is attached to a tertiary C
3) ...

Solution Summary

The solution determines the Sn2 reactions.