Bakelite is formed by the acid-catalyzed polymerization of phenol with formaldehyde.What is (are) the product(s) of the first step in this polymerization, shown below? (Note: in the answers below the hydroxymethyl group is -CH₂OH.)

Question

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The acid-catalyzed polymerization of phenol with formaldehyde involves the addition of formaldehyde with the hydroxyl group of phenol, resulting in the formation of a hydroxymethyl group (-CH2OH) attached to the benzene ring. This can occur at either the ortho (positions 2 and 6) or para (positions 3 and 5) positions of the benzene ring. Therefore, the product of the first step in this polymerization is a mixture of ortho and para-(hydroxymethyl)phenol. Option C is the only choice that correctly identifies this product. Ortho and para-hydroxybenzaldehyde (option A) and meta-hydroxybenzaldehyde (option B) are not formed in the first step of this reaction, and meta-(hydroxymethyl)phenol (option D) is not formed until later steps in the reaction.

Bakelite Is Formed by the Acid-Catalyzed Polymerization of Phenol with Formaldehyde.What