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Ch.23 Lipids
McMurry - Fundamentals of General, Organic, and Biological Chemistry 8th Edition
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoMcMurry 8th EditionCh.23 LipidsProblema 49
Capitolo 23, Problema 49

Draw the structures of all products you would obtain by saponification of the following lipid with aqueous KOH. What are the names of the products?
Chemical structure of a triacylglycerol showing bonds and functional groups for hydrolysis reactions.

Guida verificata passo dopo passo
1
Identify the type of lipid in the problem. Lipids that undergo saponification are typically triglycerides (triacylglycerols), which consist of a glycerol backbone esterified to three fatty acid chains.
Understand the saponification reaction. Saponification is the base-catalyzed hydrolysis of esters. In this case, the ester bonds in the lipid will be broken by aqueous KOH, producing glycerol and the potassium salts of the fatty acids.
Break down the lipid structure. For each ester bond in the triglyceride, replace the ester group with a hydroxyl group (-OH) on the glycerol backbone, and form a carboxylate ion (-COO⁻) for each fatty acid chain. The carboxylate ions will pair with K⁺ ions to form potassium salts of the fatty acids.
Draw the structures of the products. The first product is glycerol, which has the structure CH₂OH-CHOH-CH₂OH. The second set of products are the potassium salts of the fatty acids, which depend on the specific fatty acid chains present in the original lipid.
Name the products. The names of the products include 'glycerol' for the glycerol backbone and the names of the potassium salts of the fatty acids, which are derived from the names of the original fatty acids (e.g., potassium palmitate, potassium stearate, etc., depending on the fatty acid chains in the lipid).

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Saponification

Saponification is a chemical reaction that occurs when a lipid, typically a triglyceride, reacts with a strong base like potassium hydroxide (KOH). This process breaks down the ester bonds in the lipid, resulting in the formation of glycerol and fatty acid salts, commonly known as soap. Understanding this reaction is crucial for predicting the products formed from specific lipids.
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Percorso guidato
1:25
Ester Reactions: Saponification Concept 1

Lipids

Lipids are a diverse group of hydrophobic organic compounds, including fats, oils, and waxes, that are insoluble in water but soluble in organic solvents. They play essential roles in biological systems, such as energy storage, cellular structure, and signaling. Recognizing the type of lipid involved in the saponification process is vital for determining the specific products generated.
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Percorso guidato
1:28
Intro to Lipids Example 1

Fatty Acids

Fatty acids are carboxylic acids with long hydrocarbon chains, which can be saturated or unsaturated. During saponification, the fatty acids released from triglycerides can vary in chain length and degree of saturation, influencing the properties of the resulting soap. Identifying the specific fatty acids produced is important for understanding the characteristics of the final products.
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Percorso guidato
2:00
Fatty Acids Concept 1
Pratica correlata
Domanda del libro di testo

Dietary guidelines suggest we limit our intake of butter due to the cholesterol content and substitute oils or margarine. The following table shows the major fatty acid distribution for a typical stick of margarine and also for butter. Values are percentages.

a. Which contains more monounsaturated fatty acids?

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Domanda del libro di testo

Is the reaction shown here esterification, hydrogenation, hydrolysis, saponification, or substitution?

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Domanda del libro di testo

There are two isomeric triacylglycerol molecules whose components are glycerol, one palmitic acid unit, and two stearic acid units. Draw the structures of both, and explain how they differ.

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Domanda del libro di testo

Draw the structure of the product you would obtain on complete hydrogenation of the triacylglycerol in Problem 23.49. What is its name? Does it have a higher or lower melting temperature than the original triacylglycerol?

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Domanda del libro di testo

Tell how many different products you would obtain on hydrogenation of the triacylglycerol in Problem 23.49 if:

a. One double bond was converted to a single bond

b. Two double bonds were converted to single bonds

c. Three double bonds were converted to single bonds

d. All four double bonds were converted to single bonds

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Domanda del libro di testo

Draw the structure of glyceryl trilaurate, which is made from glycerol and three lauric acid molecules.

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