Textbook Question
Which of the following are saponifiable lipids? (Recall that ester bonds are broken by base hydrolysis.)
a. Progesterone
b. Glyceryl trioleate
c. A sphingomyelin
d. Prostaglandin E1
e. A cerebroside
f. A lecithin
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23. Lipids
Triacylglycerol Reactions: Hydrolysis
4:48 minutesProblem 35
Textbook Question
Use condensed structural formulas to write the balanced chemical equation for the NaOH saponification of glyceryl trimyristate (trimyristin).
Verified step by step guidance1
Identify the structure of glyceryl trimyristate (trimyristin). It is a triglyceride composed of a glycerol backbone esterified with three myristic acid molecules. The condensed structural formula for trimyristin is: CH₂(OCOR)CH(OCOR)CH₂(OCOR), where R represents the myristic acid chain (C₁₃H₂₇).
Write the general reaction for the saponification of a triglyceride. Saponification involves the hydrolysis of ester bonds in the triglyceride using a strong base (NaOH) to produce glycerol and the sodium salts of the fatty acids.
For the saponification of glyceryl trimyristate, write the reactants: glyceryl trimyristate (CH₂(OCOR)CH(OCOR)CH₂(OCOR)) reacts with 3 NaOH molecules (one for each ester bond).
Write the products of the reaction: The products are glycerol (CH₂OH-CHOH-CH₂OH) and three molecules of sodium myristate (C₁₃H₂₇COONa), which is the sodium salt of myristic acid.
Combine the reactants and products to write the balanced chemical equation: CH₂(OCOR)CH(OCOR)CH₂(OCOR) + 3 NaOH → CH₂OH-CHOH-CH₂OH + 3 C₁₃H₂₇COONa. Ensure the equation is balanced in terms of both atoms and charge.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Saponification
Saponification is a chemical reaction that occurs when a fat or oil reacts with a strong base, typically sodium hydroxide (NaOH), to produce glycerol and soap. In this process, the ester bonds in triglycerides are hydrolyzed, leading to the formation of fatty acid salts, which are the soap molecules. Understanding this reaction is crucial for writing the balanced equation for the saponification of glyceryl trimyristate.
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Condensed Structural Formula
A condensed structural formula is a way of representing a chemical compound that shows the arrangement of atoms and the connectivity between them without depicting all the bonds explicitly. This notation simplifies the representation of complex molecules, making it easier to visualize and balance chemical equations. For glyceryl trimyristate, the condensed formula helps in identifying the functional groups involved in the saponification reaction.
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Balancing Chemical Equations
Balancing chemical equations is the process of ensuring that the number of atoms of each element is the same on both the reactant and product sides of the equation. This is essential for obeying the law of conservation of mass, which states that matter cannot be created or destroyed in a chemical reaction. In the context of saponification, balancing the equation involves accounting for all reactants and products, including the fatty acids and glycerol produced from the reaction.
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