Predict the product of the following reactions.
(e)

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Step 1: Analyze the reactants and reaction conditions. The starting material is a brominated cyclic ether with a chiral center. The reagent is CH3SNa (sodium methanethiolate) in THF (tetrahydrofuran), which suggests a nucleophilic substitution reaction.

Step 2: Identify the type of substitution reaction. CH3SNa is a strong nucleophile, and the reaction is likely to proceed via an SN2 mechanism due to the primary nature of the carbon attached to the bromine atom. SN2 reactions involve a backside attack and inversion of configuration at the chiral center.

Step 3: Predict the nucleophilic attack. The CH3S− ion will attack the carbon bonded to the bromine atom, displacing the bromine as Br−. This results in the formation of a new bond between the carbon and the sulfur atom of CH3S−.

Step 4: Consider stereochemical implications. Since the reaction proceeds via an SN2 mechanism, the configuration at the chiral center will invert. If the starting material has an R configuration, the product will have an S configuration, and vice versa.

Step 5: Write the product structure. The product will be a cyclic ether with the sulfur atom (CH3S− group) replacing the bromine atom, and the stereochemistry at the chiral center inverted. Ensure the cyclic ether remains intact and the new substituent is correctly positioned.

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