Textbook Question
Which of the following reactions favor formation of the products? Recall that the equilibrium favors formation of the weaker acid.
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Ch. 11 - Organometallic Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 12, Problem 2
Which is more reactive, an organolithium compound or an organosodium compound? Explain your answer.
Verified step by step guidance1
Understand the reactivity of organometallic compounds: Organolithium and organosodium compounds are both organometallic compounds, meaning they contain a carbon-metal bond. Their reactivity is influenced by the polarity of this bond and the properties of the metal involved.
Compare the electronegativity of lithium and sodium: Lithium (Li) is more electronegative than sodium (Na). This means that the carbon-lithium bond is more polar than the carbon-sodium bond, leading to a greater partial negative charge on the carbon in organolithium compounds.
Analyze the bond strength: The carbon-lithium bond is shorter and stronger than the carbon-sodium bond due to the smaller size of the lithium atom compared to sodium. This stronger bond contributes to the stability of organolithium compounds, but it also makes the carbon more nucleophilic and reactive.
Consider the solubility and aggregation: Organolithium compounds tend to form aggregates in solution, but they are generally more soluble in organic solvents compared to organosodium compounds. This increased solubility enhances their reactivity in organic reactions.
Conclude the comparison: Due to the higher polarity of the carbon-lithium bond, the greater nucleophilicity of the carbon, and the better solubility in organic solvents, organolithium compounds are more reactive than organosodium compounds in most organic reactions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Organolithium Compounds
Organolithium compounds are organometallic reagents containing a carbon-lithium bond. They are highly reactive due to the strong polar nature of the C-Li bond, which makes the carbon atom nucleophilic. This reactivity allows them to readily participate in various chemical reactions, including nucleophilic additions and substitutions.
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Defining meso compounds.
Organosodium Compounds
Organosodium compounds consist of a carbon-sodium bond and are generally less reactive than organolithium compounds. The C-Na bond is less polar than the C-Li bond, resulting in a lower nucleophilicity of the carbon atom. Consequently, organosodium compounds are often used in more specialized reactions and are less versatile than their organolithium counterparts.
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Reactivity in Organometallic Chemistry
Reactivity in organometallic chemistry is influenced by the nature of the metal and the bond polarity between the metal and carbon. Organolithium compounds exhibit higher reactivity due to the stronger ionic character of the C-Li bond, making them more effective nucleophiles. In contrast, organosodium compounds, with their weaker C-Na bond, demonstrate lower reactivity, which affects their utility in synthetic applications.
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Related Practice
Textbook Question
What organometallic compound is formed from the reaction of excess methylmagnesium chloride and GaCl3?
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Textbook Question
Which of the following reactions favor formation of the products? Recall that the equilibrium favors formation of the weaker acid.
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Textbook Question
What bromo-substituted compound would be required to react with (CH2=CH)2CuLi in order to form each of the following compounds?
b.
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Textbook Question
Muscalure is the sex attractant of the common housefly. Flies are lured to traps filled with bait that contain muscalure and an insecticide. Eating the bait is fatal. How could you synthesize muscalure using 1-bromopentane as one of the starting materials?
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