Stereochemistry of SN2 Reaction: 2-Bromo-3-methylpentane

Medium Organic Chemistry Stereochemistry

Consider the following compound: 2-bromo-3-methylpentane. Determine the stereochemistry of the major product formed when this compound undergoes an SN2 reaction with sodium iodide in acetone. Identify the structure that corresponds to the major product, keeping in mind the stereochemical outcome of the reaction.

1-iodo-2-methylpentane with an (R) configuration

1-iodo-2-methylpentane with a (S) configuration

2-iodo-3-methylpentane with an (R) configuration

2-iodo-3-methylpentane with a (S) configuration

Hint

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% Correct46%