Question

Draw the curved arrow mechanism for the reaction between (2S,3S)-3,5-dimethylhexan-2-ol and PCl3. Note the specific instructions for each box. Include nonzero formal charges and lone pairs of electrons on all appropriate atoms. Then answer the question about the mechanism.

Answer 1

Answer:

(2R,3S)-2-chloro-3,5-dimethylhexane

Explanation:

As first step we have the attack of the OH group to the P atom in the PCl3 and one of the Cl atoms would leave. Then we will have a rearrangement to produce a double bond with the oyxgen on the OH. Finally the Cl produced will attack the carbon in a Sn2 substitution reaction to produce the halide with an opposite configuration.