Question

Difficulty: Very hardAlkanoic Acids, Esterification, Saponification, Fats, and Oils

Match each chemical reaction or process involving alkanoic acids, esters, fats, or oils on the left with its corresponding chemical outcome or product description on the right.

  • Acid-catalyzed esterification of propane-1,2,3-triol with hexadecanoic acidProduces tripalmitin (a saturated triglyceride) along with water molecules
  • Alkaline hydrolysis of glyceryl tristearate using excess aqueous sodium hydroxideYields propane-1,2,3-triol and sodium octadecanoate as an irreversible process
  • High-pressure catalytic hydrogenation of glyceryl trioleate in the presence of nickelConverts an unsaturated liquid vegetable triacylglycerol into a saturated solid fat
  • Acid-catalyzed reflux of ethyl ethanoate with an excess of waterReversibly produces ethanoic acid and ethanol in a state of dynamic equilibrium

Answer

The correct pairings match: (1) Acid-catalyzed esterification of propane-1,2,3-triol with hexadecanoic acid to producing tripalmitin fat and water; (2) Alkaline hydrolysis of glyceryl tristearate with aqueous NaOH to yielding propane-1,2,3-triol and sodium octadecanoate soap; (3) Catalytic hydrogenation of glyceryl trioleate to converting an unsaturated liquid triacylglycerol into a saturated solid fat; and (4) Acid-catalyzed reflux of ethyl ethanoate with water to reversibly producing ethanoic acid and ethanol.
The correct pairings logically connect each organic process to its definitive product or reaction characteristic: esterification of hexadecanoic acid with glycerol yields tripalmitin; saponification of glyceryl tristearate using NaOH irreversibly yields glycerol and sodium octadecanoate soap; catalytic hydrogenation saturates double bonds in glyceryl trioleate turning liquid oil into solid fat; and acid hydrolysis of ethyl ethanoate is a reversible equilibrium yielding ethanoic acid and ethanol.

Step-by-Step Solution

1
Analyze the reaction of propane-1,2,3-triol (glycerol) with hexadecanoic acid (palmitic acid).
Identified as esterification forming tripalmitin and water.
Hexadecanoic acid (C15H31COOHC_{15}H_{31}COOH) esterifies with glycerol to form glyceryl tripalmitin (C51H98O6C_{51}H_{98}O_6), a saturated fat.
2
Analyze the alkaline hydrolysis of glyceryl tristearate using aqueous NaOHNaOH.
Identified as saponification yielding glycerol and sodium octadecanoate.
Base hydrolysis of fats irreversibly converts ester groups into glycerol and carboxylate salts (soap).
3
Analyze the catalytic hydrogenation of glyceryl trioleate.
Identified as hardening of oils.
Addition of H2H_2 across the C=CC=C double bonds of unsaturated oleic acid residues converts liquid oil into saturated solid fat.
4
Analyze the acid-catalyzed reaction of ethyl ethanoate with water.
Identified as reversible ester hydrolysis.
Acid hydrolysis of esters is reversible, establishing an equilibrium mixture of the parent alkanoic acid (ethanoic acid) and alkanol (ethanol).

Key Concept

Reactivity and Interconversion of Alkanoic Acids, Esters, Fats, and Oils
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