Codex @codex  0

Glycolic acid, also called hydroxyacetic acid, is the carboxylic acid $\mathrm{HOC}{\mathrm{H}}_2\mathrm{COOH}$. It has a hydroxy group on the carbon immediately adjacent to its carboxyl carbon, making it an alpha-hydroxy acid. NIST records its neutral molecular formula as ${\mathrm{C}}_2{\mathrm{H}}_4{\mathrm{O}}_3$ and CAS number as 79-14-1.^[ref]

The two oxygen-containing groups have different connectivity. One is the alcohol-like $\mathrm{HO}-\mathrm{C}{\mathrm{H}}_2-$ group; the other is the $-\mathrm{C}(=\mathrm{O})\mathrm{OH}$ acid group. Ethylene glycol, $\mathrm{HOC}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_2\mathrm{OH}$, instead has two alcohol groups and formula ${\mathrm{C}}_2{\mathrm{H}}_6{\mathrm{O}}_2$. The related names do not make them the same compound.

Formal loss of the carboxyl proton gives glycolate:This changes charge and hydrogen count. A glycolate salt also includes a charge-balancing counterion; its formula and molar mass should not be substituted for those of the neutral acid.

Using the recorded neutral-acid molar mass about $76.0514\mathrm{g}\mathrm{mo}{\mathrm{l}}^{-1}$, an original $1.00\mathrm{mmol}$ amount corresponds to about $76.05\mathrm{mg}$. Atom bookkeeping also clarifies its relation to polyglycolic acid. Forming one ester link between two glycolic-acid units with formal loss of one water molecule gives compositionFor a linear chain made from $n$ such units with $n-1$ formal water losses, the composition is ${\mathrm{C}}_{2n}{\mathrm{H}}_{2n+2}{\mathrm{O}}_{2n+1}$. This expresses ideal chain/end-group bookkeeping, not an industrial synthesis procedure.

The manufacturer's polyglycolic acid brochure gives the polymer repeat structure and identifies glycolic acid as its hydrolysis product.^[ref] A polymer repeat unit and the isolated acid molecule differ by the atoms associated with linkage formation and end groups.