4.5.6 · D5Biomolecules
Question bank — Lipids — fatty acids, triglycerides, phospholipids; saponification
Reveal format: read the left of :::, answer, then check the right.
True or false — justify
Lipids are a single class of molecule with one shared functional group.
False. Lipids are defined by a property (insolubility in water), not a shared structure — fatty acids, triglycerides, phospholipids and steroids look very different yet all count.
A saturated fatty acid always has a higher melting point than an unsaturated one of the same chain length.
True. No C=C means straight chains that stack tightly → stronger Van der Waals Forces → more energy needed to melt. The kink from a cis double bond spoils this packing.
Adding more double bonds makes a fatty acid melt at a higher temperature.
False, and a classic trap. Each cis double bond adds a kink, so more double bonds = worse packing = lower melting point. "Double bond" sounds strong but here it weakens the intermolecular contact.
A triglyceride is amphipathic.
False. All three glycerol –OH groups hold hydrophobic fatty-acid tails, so the whole molecule is hydrophobic. Only phospholipids (one tail swapped for a polar phosphate) are amphipathic.
Saponification is just esterification run backwards.
Half-true. It reverses the bond (ester → carboxylate), but esterification releases water while saponification consumes it AND the base traps the product, so it's not a simple reversal — it's driven one way.
Soap and phospholipids clean/organise water by the same physical principle.
True. Both are amphipathic — hydrophobic tail hides from water, hydrophilic head faces it. Soap forms micelles around grease; phospholipids form bilayers; same "hide the tails" logic.
Glycerol is released in both esterification of a triglyceride and its saponification.
False. Glycerol is a product of saponification (bonds broken) but a reactant in building a triglyceride (bonds made). Don't confuse the two directions.
Every carboxylic acid is a fatty acid.
False. A fatty acid needs a long unbranched hydrocarbon chain plus the –COOH. Acetic acid () is a carboxylic acid but far too short to be a fatty acid.
Spot the error
"Saponification of tristearin gives glycerol + 3 stearic acid."
Error: in basic medium the released acid is instantly neutralised, so you get 3 sodium stearate (the soap, ), not free stearic acid. Free acid appears only in acidic hydrolysis.
"A triglyceride forms from glycerol + 3 fatty acids and releases 1 water."
Error: 3 waters. Each ester bond is one condensation, and three ester bonds form, so three leave — one per bond.
"Phospholipids replace all three fatty acids with phosphate groups."
Error: only one –OH holds a phosphate; the other two still hold fatty-acid tails. That one swap is exactly what creates the two-tails-one-head amphipathic shape.
"Fats store more energy than sugars because they contain more oxygen."
Error: it's the opposite — fatty-acid carbons are highly reduced (many C–H bonds, little oxygen). Oxidising those C–H bonds via Energy Metabolism — Beta Oxidation releases the big energy (~9 vs ~4 kcal/g).
"Acid hydrolysis of a triglyceride goes to completion, so we use acid to make soap."
Error: acid hydrolysis is an equilibrium and reverses easily. Base is used for soap because it converts the acid to a non-reactive salt, trapping the reaction forward — that's why it's saponification.
"The kink in an unsaturated fatty acid comes from the –COOH head."
Error: the kink comes from a cis C=C double bond in the tail, which bends the chain like a hockey stick. The –COOH head is the same in saturated and unsaturated acids.
"In a bilayer the phosphate heads point inward to hide from water."
Error: the heads are hydrophilic, so they face the water on both surfaces; the hydrophobic tails tuck inward away from water. You've inverted the Cell Membrane Structure.
Why questions
Why do natural fatty acids almost always have an even number of carbons?
Because the body builds them two carbons at a time from acetyl (a 2-carbon unit), so the total keeps landing on an even number.
Why is fat a more compact fuel store than carbohydrate, beyond just energy density?
Fat is anhydrous — it stores without dragging water along, while carbohydrate stores are hydrated. So fat is lighter and denser per usable joule.
Why does NaOH, and not just water, drive saponification fully forward?
The base grabs each released fatty acid and turns it into a carboxylate salt that cannot re-form the ester, so the equilibrium is trapped in the forward direction (see Hydrolysis Reactions).
Why does a cis double bond lower melting point but a trans one barely does?
A cis bond bends the chain, ruining tight packing; a trans bond keeps the chain nearly straight, so packing (and melting point) stays close to the saturated case.
Why can phospholipids self-assemble into membranes "with no instructions"?
Physics alone: water pushes the hydrophobic tails together and lets the hydrophilic heads face water, and the lowest-energy arrangement of that compromise is a bilayer sheet — no template needed.
Why is the shorthand more useful than just writing "oleic acid"?
It encodes the two properties that matter at a glance — chain length (18 → melting trend) and unsaturation (1 double bond → kink, reactivity) — in two numbers.
Edge cases
What happens to melting point if you fully hydrogenate an unsaturated oil (remove all C=C)?
The kinks vanish, chains straighten, packing improves → melting point rises, turning liquid oil into a solid fat. This is exactly how margarine is made.
Is a fatty acid with zero double bonds still called "unsaturated" if it has one methyl branch?
No. Saturation refers only to C=C double bonds; a branch affects packing but a chain with no C=C is saturated regardless of branching.
What if you saponify with KOH instead of NaOH?
Same reaction, but you get potassium salts of the fatty acids — softer, more soluble "soft soaps" — plus glycerol. The choice of base changes the counter-ion, not the mechanism.
Can a very short-chain carboxylate (say acetate) form a working soap/micelle?
No. Its hydrocarbon tail is too short to be meaningfully hydrophobic, so there's no strong drive to bury tails and form a micelle — it just dissolves. You need a long tail, i.e. an actual fatty-acid salt (see Soaps and Detergents).
What is the amphipathic behaviour of a molecule with two tails and one head versus one tail and one head?
Two-tailed (phospholipid) favours flat bilayers/membranes; one-tailed (soap) favours curved micelles. Head-to-tail geometry decides the shape that self-assembles.
If glycerol had only two –OH groups instead of three, what could it no longer form?
It could not form a triglyceride (needs 3 ester attachment points); at most a di-substituted glyceride, changing both energy-storage capacity and the phospholipid architecture.