Textbook Question
Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).
(b) H2 , Ni (partial hydrogenation)
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Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 26, Problem 59a
Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).
(a) H2 , Pd
Verified step by step guidance1
Step 1: Analyze the structure of linoleate triglyceride. It consists of a glycerol backbone esterified with three fatty acid chains, each containing two double bonds in the cis configuration.
Step 2: Understand the reaction conditions. The presence of H₂ and Pd indicates a catalytic hydrogenation reaction, which typically reduces double bonds in unsaturated compounds to single bonds.
Step 3: Predict the effect of hydrogenation on the fatty acid chains. The double bonds in the linoleate triglyceride will be converted to single bonds, resulting in saturated fatty acid chains.
Step 4: Note that the glycerol backbone and ester linkages remain unaffected during hydrogenation, as the reaction specifically targets the double bonds in the fatty acid chains.
Step 5: The final product will be a triglyceride with fully saturated fatty acid chains, as all double bonds are reduced to single bonds under these conditions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Triglycerides
Triglycerides are esters formed from glycerol and three fatty acids. They are the main constituents of body fat in humans and animals, as well as vegetable fat. In the case of linoleic acid, which is a polyunsaturated fatty acid, the triglyceride will contain multiple double bonds, influencing its reactivity and the products formed during chemical reactions.
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Triacylglycerol Reactions: Hydrogenation Example 1
Hydrogenation
Hydrogenation is a chemical reaction that involves the addition of hydrogen (H₂) to unsaturated bonds, typically double bonds in alkenes or alkynes. In the presence of a catalyst like palladium (Pd), hydrogenation converts unsaturated fatty acids into saturated ones, which can alter the physical properties of the triglyceride, such as melting point and stability.
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00:48The definition of hydrogenation.
Linoleic Acid
Linoleic acid is an essential polyunsaturated fatty acid with two double bonds, classified as an omega-6 fatty acid. It plays a crucial role in human health and is a key component of cell membranes. Understanding its structure and reactivity is vital for predicting the outcome of reactions, such as hydrogenation, which can lead to the formation of different fatty acid derivatives.
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Related Practice
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Textbook Question
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Textbook Question
In each of the disaccharides shown (a–c), (i) identify the reducing end of the sugar, (ii) tell what monosaccharides are used to make it, and (iii) tell what type of glycoside linkage is present.
(b)
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