Chemistry Labs

Grade 9

Lipids and fats

Fats and oils are esters of glycerol with fatty acids; they store energy, do not mix with water, and can be turned into soap.

IntuitionIntuition: why oil and water do not mix

Shake cooking oil with water and the oil soon gathers in a separate layer. Fat molecules are mostly long chains of carbon and hydrogen, which do not attract water molecules. The same chains make fats a compact energy store: a gram of fat gives more than twice the energy of a gram of starch or sugar.

Glycerol (left) carries three fatty-acid chains joined by ester links; the lowest chain has a cis double bond that bends it. Hydrogens are omitted.

SchoolSchool level: structure, saturated and unsaturated fats, soap

Definition:

An ester formed from one glycerol molecule HOCHX2−CHOH−CHX2OH\ce{HOCH2-CHOH-CH2OH} and three fatty acids (long-chain carboxylic acids R−COOH\ce{R-COOH}). Solid ones are called fats, liquid ones oils.

CX3HX5(OH)X3+3 RCOOH⇌HX+CX3HX5(OCOR)X3+3 HX2O\ce{C3H5(OH)3 + 3 RCOOH <=>[H+] C3H5(OCOR)3 + 3 H2O}
Common fatty acids
Fatty acidFormulaType
Palmitic acidC₁₅H₃₁COOHSaturated
Stearic acidC₁₇H₃₅COOHSaturated
Oleic acidC₁₇H₃₃COOH (one cis C=C)Unsaturated

Saturated chains are straight and pack closely, so animal fats such as lard are solid at room temperature. A cis C=C double bond bends the chain, so molecules pack poorly and plant oils such as olive oil stay liquid. Heating a fat with aqueous NaOH breaks the ester bonds (saponification) and gives glycerol and soap, the sodium salt of fatty acids.

(CX17HX35COO)X3CX3HX5+3 NaOH→3 CX17HX35COONa+CX3HX5(OH)X3\ce{(C17H35COO)3C3H5 + 3 NaOH -> 3 C17H35COONa + C3H5(OH)3}

Example: Soap from tristearin

Saponify 89 g of tristearin, (CX17HX35COO)X3CX3HX5\ce{(C17H35COO)3C3H5} (M = 890 g/mol), with excess NaOH. What mass of sodium stearate (M = 306 g/mol) forms?

Solution

n(tristearin) = 89/890 = 0.100 mol. One mole gives 3 mol of soap, so n(soap) = 0.300 mol and m = 0.300 × 306 = 91.8 g.

References

  • Lehninger Principles of Biochemistry (8th ed.) · David L. Nelson, Michael M. Cox, Aaron A. Hoskins, 2021