Textbook Question
Identify the isoprene units in the terpenes shown. In cross-linked or ring-containing terpenes, linkages can be formed between more than just C1 and C4 of isoprene.
(b)
2
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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 59b
Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).
(b) H2 , Ni (partial hydrogenation)
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 a cis configuration.
Step 2: Understand the reaction conditions. Partial hydrogenation involves the addition of hydrogen (H₂) in the presence of a nickel (Ni) catalyst, which selectively reduces some of the double bonds in the fatty acid chains.
Step 3: Predict the effect of partial hydrogenation. Under these conditions, one or more of the double bonds in the fatty acid chains may be converted to single bonds, resulting in a mixture of saturated and unsaturated fatty acids. The cis configuration of the double bonds may also be converted to trans configuration in some cases.
Step 4: Consider the product structure. After partial hydrogenation, the triglyceride will have fewer double bonds, and some of the double bonds may be converted to trans isomers. The exact product depends on the extent of hydrogenation and the selectivity of the catalyst.
Step 5: Note the implications. Partial hydrogenation is commonly used in the food industry to produce semi-solid fats, but it can lead to the formation of trans fats, which are associated with health risks.
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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, a polyunsaturated fatty acid, its triglyceride form can undergo various chemical reactions, including hydrogenation, which alters its saturation level.
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Triacylglycerol Reactions: Hydrogenation Example 1
Partial Hydrogenation
Partial hydrogenation is a chemical process that adds hydrogen to unsaturated fats, converting some double bonds into single bonds. This process can increase the stability and shelf life of oils but may also lead to the formation of trans fats. In the context of linoleate, partial hydrogenation will convert some of its double bonds, resulting in a product with fewer unsaturated sites.
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Linoleic Acid
Linoleic acid is an essential polyunsaturated fatty acid that is crucial for human health. It contains two double bonds and is classified as an omega-6 fatty acid. Understanding its structure and properties is vital for predicting the outcomes of chemical reactions, such as hydrogenation, which can affect its nutritional value and physical characteristics.
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Related Practice
Textbook Question
Identify the isoprene units in the terpenes shown. In cross-linked or ring-containing terpenes, linkages can be formed between more than just C1 and C4 of isoprene.
(a)
1
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Textbook Question
Draw a mechanism for the acid-catalyzed, nonenzymatic conversion of DPP to IPP. How do you know your mechanism is correct?
1
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Textbook Question
Maltose, like cellobiose, is composed of two glucose units. What is the difference between maltose and cellobiose?
1
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Textbook Question
Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).
(a) H2 , Pd
6
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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)
1
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