☰ Contents · Chemistry (Organic chemistry)

Carboxylic acids

Lessons 26 · 1 lessons · A. Mutalibov, E. Murodov, S. Masharipov, H. Islomova. Organic Chemistry, Grade 10, 1st edition. G‘afur G‘ulom Publishing House, Tashkent, 2017
26

Carboxylic acids: preparation and properties

Textbook: pp. 102–107
GoalWrite the structure, naming, preparation and properties of carboxylic acids (salts, esterification, halogenation).
New words
carboxyl group · karboksil guruhcarboxylic acids · karbon kislotalarneutralization · neytrallanishhigher fatty acids · yuqori yog‘ kislotalar
Explanation

Compounds containing the carboxyl group –COOH are carboxylic acids; saturated monobasic acids are CₙH₂ₙ₊₁COOH (in formic acid HCOOH the “radical” is just H). Trivial names show their origin: formic (HCOOH), acetic (CH₃COOH), propionic, butyric, valeric, caproic acid; palmitic C₁₅H₃₁COOH and stearic C₁₇H₃₅COOH are higher fatty acids. Systematic names: alkane name + “oic acid” (ethanoic acid), numbering from the carboxyl carbon: 3-methylbutanoic acid. Preparation: oxidizing aldehydes and primary alcohols, hydrolyzing esters, acting on their salts with a strong acid: 2CH₃COONa + H₂SO₄ → 2CH₃COOH + Na₂SO₄. As weak acids they react with metals (2CH₃COOH + Mg → (CH₃COO)₂Mg + H₂), basic oxides, bases (CH₃COOH + NaOH → CH₃COONa + H₂O) and carbonates (2CH₃COOH + CaCO₃ → (CH₃COO)₂Ca + H₂O + CO₂↑). With alcohols they form esters (esterification), and a hydrogen of the radical can be replaced by halogen in light or with a catalyst: CH₃COOH + Cl₂ → ClCH₂COOH + HCl. Formic acid also has an aldehyde group, so it gives the silver mirror reaction. Table vinegar is a dilute (about 3–9 %) solution of acetic acid; the concentrated acid burns the skin.

Worked examples
60 g of acetic acid (1 mol) with NaOH gives 82 g of sodium acetate. 120 g of acetic acid (2 mol) with CaCO₃ releases 1 mol of CO₂, i.e. 44 g of gas.
Acids of C₄H₈O₂: butanoic acid CH₃CH₂CH₂COOH and 2-methylpropanoic acid (CH₃)₂CHCOOH. 2CH₃CH₂CH₂COONa + H₂SO₄ → 2CH₃CH₂CH₂COOH + Na₂SO₄.
Class activity

Read the ingredient label of household vinegar (concentration, percent); do not mix anything. Acetic acid is hazardous when concentrated. In class only the teacher demonstrates reactions with carbonates and magnesium.

Practice
1
Give the formula and systematic name of acetic acid.
2
How many grams of sodium acetate (M = 82) form when 60 g of acetic acid are neutralized with NaOH?
3
How many grams of CO₂ are released when 120 g of acetic acid react with excess CaCO₃ (2CH₃COOH gives 1 CO₂)?
4
Why does formic acid give the silver mirror reaction while acetic acid does not?