Question

The molecule below is used in the chemical industry to dilute hydraulic fluids. Draw the major organic product when it reacts with thionyl chloride. Include wedge-and-dash bonds to show the stereochemistry of the product.

Answer 1

Concepts and reason

The concept used to solve this problem is ${{\rm{S}}_{\rm{N}}}{\rm{2}}$ . The substrate is secondary alcohol and the reagent is thionyl chloride.

Thionyl chloride converts the alcohol to alkyl chlorides.

Fundamentals

${{\rm{S}}_{\rm{N}}}{\rm{2}}$ reaction is a single step reaction. The rate of the reaction depends on both concentration of substrate and concentration of nucleophile.

In ${{\rm{S}}_{\rm{N}}}{\rm{2}}$ , the attack of nucleophile takes place from the back side, so inversion of configuration takes place in the product.

Primary and secondary alcohols can be converted to the alkyl halides using thionyl chloride and phosphorous tribromide.

The structures of reactant and the reagent is as follows:

The reaction is as follows:

Ans:

The major organic product is as follows: