Questions: Predict the major organic product for each of the following reactions. Be sure to clearly indicate the proper stereochemical relationships between groups (if appropriate), and write the word "racemic" next to any compound that is formed as a racemic mixture.

Predict the major organic product for each of the following reactions. Be sure to clearly indicate the proper stereochemical relationships between groups (if appropriate), and write the word "racemic" next to any compound that is formed as a racemic mixture.

Transcript text: Predict the major organic product for each of the following reactions. Be sure to clearly indicate the proper stereochemical relationships between groups (if appropriate), and write the word "racemic" next to any compound that is formed as a racemic mixture.

Solution

Solution Steps

Step 1: Identify the reaction type

The given reaction is an Sn1 reaction. The reactant is a secondary alkyl halide, and the reagent is methanol (CH3OH), which acts as a weak nucleophile and solvent. Heat promotes the Sn1 mechanism.

Step 2: Show the mechanism

The bromide leaves, forming a secondary carbocation. This carbocation is planar, making it susceptible to attack from either face.
Methanol attacks the carbocation from either side.
Another methanol molecule deprotonates the attached methanol, forming the final ether product.

Step 3: Draw the major product(s)

Since the carbocation intermediate is planar, the nucleophile (methanol) can attack from either side, resulting in a racemic mixture of products.