Predict the product of the following reactions.
(e)

Verified step by step guidance

1. 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.
2. 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.
3. 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−.
4. 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.
5. 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.

Key Concepts

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity patterns and the types of reactions that can occur. This knowledge is essential for determining the products of organic reactions.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is important for predicting the products of reactions, especially in cases where chirality or geometric isomerism is involved. Understanding stereochemistry helps in determining the specific isomers that may be produced in a reaction.