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 62b
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) 
Verified step by step guidance1
Step 1: Understand the structure of isoprene units. Isoprene is a 5-carbon molecule with the formula C₅H₈, consisting of two double bonds. In terpenes, isoprene units are linked together in various ways, often through C₁-C₄ linkages, but other linkages are possible.
Step 2: Analyze the structure of farnesol provided in the image. Farnesol is a sesquiterpene, meaning it is composed of three isoprene units. Look for repeating patterns of 5-carbon units within the molecule.
Step 3: Identify the isoprene units in farnesol. Start by locating the double bonds and methyl groups, which are characteristic features of isoprene units. Divide the molecule into three distinct 5-carbon segments based on these features.
Step 4: Note the linkages between the isoprene units. In farnesol, the isoprene units are connected in a head-to-tail fashion, meaning the C₁ of one isoprene unit is linked to the C₄ of the next. Observe any deviations from this pattern, such as cross-linking or ring formation.
Step 5: Highlight the functional group present in farnesol. The hydroxyl (-OH) group at the end of the molecule is an important feature that distinguishes farnesol from other terpenes. This group does not affect the identification of isoprene units but is relevant for understanding the molecule's reactivity and properties.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Isoprene Units
Isoprene units are the fundamental building blocks of terpenes, consisting of a five-carbon structure with the formula C₅H₈. These units can polymerize to form larger molecules, and in terpenes, they typically connect in a head-to-tail fashion. Understanding how these units combine is crucial for identifying the structure of various terpenes.
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Terpene Structure
Terpenes are a diverse class of organic compounds produced by many plants, characterized by their strong odors and roles in plant defense. They are classified based on the number of isoprene units they contain, such as monoterpenes (two units) and sesquiterpenes (three units). Recognizing the structural variations, including rings and cross-linkages, is essential for analyzing their chemical properties.
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Linkages in Terpenes
In terpenes, linkages can occur not only between the C₁ and C₄ positions of isoprene units but also at other carbon positions, especially in cyclic or cross-linked structures. This flexibility in bonding leads to a variety of structural forms and functional properties. Understanding these linkages is vital for accurately identifying and classifying different terpenes.
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Related Practice
Textbook Question
Suggest a mechanism by which TXB2 might be formed from TXA2 in an acid-catalyzed hydrolysis reaction. [The structure has been simplified.]
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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)
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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?
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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.
(e)
826
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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.
(c)
953
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