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 60
Draw a mechanism for the acid-catalyzed, nonenzymatic conversion of DPP to IPP. How do you know your mechanism is correct?
Verified step by step guidance1
Step 1: Identify the reactant (DPP) and product (IPP) structures. DPP contains a phosphate group attached to an isopentenyl chain, while IPP has a double bond in the isopentenyl chain. The reaction is acid-catalyzed, meaning H2SO4 provides protons to facilitate the mechanism.
Step 2: Protonation of the phosphate group occurs first. The acidic environment (H2SO4) donates a proton (H⁺) to one of the oxygen atoms on the phosphate group, increasing its electrophilicity and making it more susceptible to nucleophilic attack.
Step 3: A rearrangement occurs in the isopentenyl chain. The protonated phosphate group facilitates the formation of a carbocation intermediate by breaking the bond between the phosphate group and the isopentenyl chain. This carbocation is stabilized by resonance within the isopentenyl structure.
Step 4: Deprotonation of the carbocation intermediate leads to the formation of the double bond in the isopentenyl chain. A base (likely water or another molecule in the acidic solution) abstracts a proton from the carbocation, resulting in the formation of the double bond.
Step 5: The final product (IPP) is formed, with the double bond in the isopentenyl chain and the phosphate group remaining intact. The mechanism is correct because it follows the principles of acid-catalyzed reactions, including protonation, carbocation formation, and deprotonation steps.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Catalyzed Reactions
Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In this context, the acid (H2SO4) donates protons (H+) to the reactants, facilitating the formation of intermediates that lead to the desired products. This mechanism often includes protonation steps that stabilize reactive species, making it essential to understand how acids influence reaction pathways.
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Mechanism of Phosphate Ester Hydrolysis
The conversion of DPP to IPP involves the hydrolysis of phosphate esters, where water plays a crucial role in breaking the P-O bonds. Understanding the mechanism requires knowledge of nucleophilic attack by water on the phosphorus atom, leading to the formation of intermediates and ultimately the products. This process is vital in biochemical pathways and is influenced by the presence of acid, which can enhance the reaction rate.
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Reaction Mechanism Validation
To validate a proposed reaction mechanism, one must ensure that it aligns with experimental observations and theoretical principles. This includes checking for the correct stoichiometry, identifying intermediates, and confirming that the energy profile of the reaction is feasible. Additionally, comparing the predicted products with those obtained experimentally is crucial for establishing the accuracy of the mechanism.
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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.
(b)
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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
Maltose, like cellobiose, is composed of two glucose units. What is the difference between maltose and cellobiose?
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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
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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)
2
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