Question

Draw the major organic substitution product(s) for (2R,3S)-2-bromo-3-methylpentane reacting with the given nucleophile. Indicate the stereochemistry, including H\'s, at each stereogenic center. Omit any byproducts.

Answer 1

Answer:

(2R,3S)-2-ethoxy-3-methylpentane

and

(2S,3S)-2-ethoxy-3-methylpentane

Explanation:

For this case, we will have  $CH_3CH_2O^-$ as nucleophile. Also, this compound is also in excess. So, we will have as solvent $CH_3CH_2OH$ a protic solvent. Therefore the Sn1 reaction would be favored.

The first step would be the carbocation formation followed by the attack of the nucleophile. In this case both isomers would be produced: R and S (see figure).