Carboxylic Acids 🍋

What is a carboxylic acid?

• compound w/ a carboxyl group (-COOH)

  • which is a combo of a carbonyl (C=O) and a hydroxyl (-OH) group on the same carbon

What is the general formula of a carboxylic acid?

• R–COOH

• R: hydrocarbon chain / hydrogen

What makes carboxylic acids acidic?

• hydrogen from –OH group dissociates

  • releasing H⁺ (a proton)

    • making it weakly acidic

Give two examples of carboxylic acids found in everyday life.

• Acetic acid (vinegar)

• citric acid (lemon).

What is the functional group of a carboxylic acid?

The carboxyl group: –COOH.

How do you name a carboxylic acid?

• Take the alkane name and replace the -e with -oic acid

  • E.g., Methane → Methanoic acid (HCOOH)

  • Ethane → Ethanoic acid (CH₃COOH)

Are carboxylic acids polar or non-polar?

• Polar

• b/c of the electronegative oxygen atoms and their ability to form hydrogen bonds

Are carboxylic acids soluble in water?

• small ones are very soluble due to hydrogen bonding

• solubility decreases w/ larger hydrocarbon chains

What kind of intermolecular forces do carboxylic acids exhibit?

• Hydrogen bonding (strong)

• dipole-dipole forces

What happens when a carboxylic acid reacts with a base?

• It forms a carboxylate salt and water

  • (e.g., CH₃COOH + NaOH → CH₃COO⁻ Na⁺ + H₂O).

What is esterification?

• A carboxylic acid + alcohol → ester + water

• in the presence of an acid catalyst (H₂SO₄)

What is the product of reacting a carboxylic acid with an alcohol?

1. An ester (–COOR)

2. water

How do carboxylic acids behave in oxidation reactions?

Primary alcohols and aldehydes
—> oxidized to carboxylic acids

What’s a carboxylate ion?

• The conjugate base of a carboxylic acid

• formed after it loses a proton (e.g., CH₃COO⁻)

Why are carboxylic acids stronger acids than alcohols?

• negative charge on the carboxylate ion is resonance-stabilized

  • making it easier to lose H⁺

Where are carboxylic acids found in biology?

in fatty acids, amino acids, and hormones