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2.20

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Organic Chemistry
Found in: Page 74

Short Answer

Glycolic acid, , is the simplest member of a group of compounds called α-hydroxy acids, ingredients in skin care products that have an OH group on the carbon adjacent to a group. Would you expect to be a stronger or weaker acid than acetic acid, ?

Glycolic acid is a stronger acid than acetic acid.

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Step by Step Solution

Acid and its conjugate base

The acid’s strength is inversely correlated to the stability of its conjugate base (species obtained after the ion loss from the parent molecule/acid).

The more stable (weaker) is the conjugate base, the stronger is the acid.

Stability of the conjugate base

The loss of a proton from a molecule increases the resulting molecule’s electron density. The molecules that can stabilize excess electron density react very slowly,i.e., they are stable.

The presence of electron-withdrawing groups on the molecule leads to higher stability of the conjugate base.

Acidic strength of glycolic and acetic acid

Glycolic acid ( ) consists of one more oxygen atom from acetic acid ( ). Hence, it can stabilize the conjugate base more effectively.

The conjugate base of glycolic acid is more stable (less reactive) than that of acetic acid.

Therefore, glycolic acid is more acidic than acetic acid.

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