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Write a mechanism to explain the following reaction. When naphthalene is reacted with formaldehyde and hydrochloric...

Write a mechanism to explain the following reaction. When naphthalene is reacted with formaldehyde and hydrochloric acid, the product is 1-chlormethylnaphthalene. Be sure your mechanism explains the regiochemistry as well as the product.

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Answer #1

Given below is the mechanism of the formation of 1-chlormethylnaphthalene from the Fridel-Crafts alkylation reaction between naphthalene, formaldehyde and HCl. The first step is formation of electrophilic reagent from HCHO and HCl by protonation of C=O oxygen. The electrophile is attacked by naphthalene pi-electrons to form an intermediate which looses a H and rearomatization occurs to give 1-hydroxymethylnaphthalene. This then undergoes an SN2 reaction with HCl to give the desired end product.

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