The general structure of phenol formaldehyde resin and mechanism of its formation under acidic conditions is to be shown. Concept Introduction: Phenol reacts with formaldehyde in the presence of the catalyst to form phenol formaldehyde resin called Bakelite. This polymerization reaction proceeds through the formation of carbocation of formaldehyde. To determine: The structure of Bakelite and mechanism of its formation under acidic conditions.

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Chapter 26, Problem 26.33SP

Interpretation Introduction

Interpretation: The general structure of phenol formaldehyde resin and mechanism of its formation under acidic conditions is to be shown.

Concept Introduction: Phenol reacts with formaldehyde in the presence of the catalyst to form phenol formaldehyde resin called Bakelite. This polymerization reaction proceeds through the formation of carbocation of formaldehyde.

To determine: The structure of Bakelite and mechanism of its formation under acidic conditions.

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One of the earliest commercial plastics was Bakelite®, formed by the reaction of phenol with a little more than one equivalent of formaldehyde under acidic or basic conditions. Baeyer first discovered this reaction in 1872, and practical methods for casting and molding Bakelite were developed around 1909. Phenol-formaldehyde plastics and resins (also called phenolics) are highly cross-linked because each phenol ring has three sites (two ortho and one para) that can be linked by condensation with formaldehyde. Suggest a general structure for a phenol-formaldehyde resin, and propose a mechanism for its formation under acidic conditions.

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