Carboxylic acids and derivatives

MDCAT Chemistry · Chemistry · Carboxylic acids. The idea in plain words, the rules to remember, the mistake to avoid and a worked example, written and checked by Mega Lecture.

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The idea

Carboxylic acids contain the –COOH group. They are weak acids, yet far stronger than alcohols or phenol, because the negative charge of the carboxylate ion, RCOO−, is shared equally between two oxygen atoms. Groups that pull electrons away, such as Cl, make the acid stronger. Alkyl groups push electrons and make it weaker.

Replacing the –OH of the acid gives the derivatives: acid chlorides (RCOCl), anhydrides, esters (RCOOR′) and amides (RCONH2).

Acids and their derivatives react by nucleophilic substitution, not addition, because the carbonyl carbon carries a group that can leave. The better the leaving group, the more reactive the derivative.

Rules to remember

Common mistake

Students name an ester the wrong way round. The first word comes from the alcohol and the second from the acid: HCOOCH2CH3 is ethyl methanoate, made from methanoic acid and ethanol.

Worked example

3.0 g of ethanoic acid reacts with excess ethanol and a little concentrated H2SO4. The yield of ethyl ethanoate is 60%. What mass of ester is obtained? (H = 1, C = 12, O = 16)

  1. CH3COOH + C2H5OH ⇌ CH3COOC2H5 + H2O, a 1 : 1 ratio. Moles of acid = 3.0 ÷ 60 = 0.050 mol.
  2. Mr of ethyl ethanoate, C4H8O2 = 48 + 8 + 32 = 88, so the maximum mass = 0.050 × 88 = 4.4 g.
  3. Actual mass = 60% of 4.4 = 0.60 × 4.4 = 2.64 g.

Answer: 2.64 g of ethyl ethanoate (about 2.6 g)

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