What is the major product of the reaction between methanol and (2R,3S)-2-bromo-3-methylpentane at room temperature?

Question

What is the major product of the reaction between methanol and (2R,3S)-2-bromo-3-methylpentane at room temperature?

Answer 1

To determine the major product of the reaction between methanol and (2R,3S)-2-bromo-3-methylpentane at room temperature, we need to consider the reaction mechanism and the relative reactivity of the reactants.

The reaction between methanol (CH3OH) and (2R,3S)-2-bromo-3-methylpentane is an example of a substitution reaction, specifically an SN2 (substitution nucleophilic bimolecular) reaction. In this type of reaction, the nucleophile (methanol) attacks the electrophilic carbon (the carbon attached to the bromine) and displaces the leaving group (bromine).

First, let's evaluate the reactivity and stereochemistry of (2R,3S)-2-bromo-3-methylpentane. The 2-bromo-3-methylpentane molecule contains an asymmetric carbon (the chiral center), so it has enantiomers. Here, (2R,3S)-2-bromo-3-methylpentane indicates the stereochemistry.

Now, let's consider the reaction mechanism. In an SN2 reaction, the nucleophile attacks the carbon attached to the leaving group from the backside, resulting in an inversion of the stereochemistry at the chiral center.

In this case, the methanol molecule acts as the nucleophile. It attacks the carbon that is attached to the bromine atom, and the bromine is displaced, resulting in the formation of a new bond between the carbon and the oxygen of methanol.

Based on the reaction mechanism and the inversion of stereochemistry, the major product of this reaction will be (2R,3R)-2-methoxy-3-methylpentane.

To verify this, we need to draw the structure of the product based on the reaction mechanism and the stereochemical outcome.