Textbook Question
Fill in the squares in the following chemical equations:
a.
b.
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Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides
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
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Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 79
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 79Chapter 10, Problem 79
Would you expect methoxide ion to be a better nucleophile if it is dissolved in CH3OH or if it is dissolved in DMSO? Why?
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Understand the role of the solvent in nucleophilicity: Solvents can significantly affect the nucleophilicity of a species. Polar protic solvents (e.g., CH3OH) can hydrogen bond with the nucleophile, stabilizing it and reducing its reactivity. Polar aprotic solvents (e.g., DMSO) do not hydrogen bond with the nucleophile, allowing it to remain more reactive.
Analyze the nature of methoxide ion (CH3O⁻): Methoxide ion is a strong nucleophile because it has a negatively charged oxygen atom with a lone pair of electrons that can attack an electrophile.
Consider methoxide ion in CH3OH (methanol): Methanol is a polar protic solvent. It can form hydrogen bonds with the methoxide ion, stabilizing it and reducing its nucleophilicity. This means the methoxide ion will be less reactive in methanol.
Consider methoxide ion in DMSO (dimethyl sulfoxide): DMSO is a polar aprotic solvent. It does not form hydrogen bonds with the methoxide ion, so the ion remains less stabilized and more reactive. This enhances the nucleophilicity of methoxide ion in DMSO.
Conclude: Methoxide ion will be a better nucleophile when dissolved in DMSO compared to CH3OH because DMSO does not stabilize the ion through hydrogen bonding, allowing it to remain more reactive.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilicity
Nucleophilicity refers to the ability of a species to donate an electron pair to an electrophile, forming a chemical bond. It is influenced by factors such as charge, electronegativity, and solvent effects. Stronger nucleophiles are typically more reactive in nucleophilic substitution reactions, making understanding this concept essential for predicting reaction outcomes.
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Nucleophilic Addition
Solvent Effects
The choice of solvent can significantly impact nucleophilicity. Protic solvents, like methanol (CH3OH), can stabilize nucleophiles through hydrogen bonding, potentially reducing their reactivity. In contrast, aprotic solvents, such as dimethyl sulfoxide (DMSO), do not stabilize nucleophiles as much, often leading to increased nucleophilicity and reactivity in reactions.
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Methoxide Ion (CH3O-)
The methoxide ion is a strong nucleophile derived from methanol by deprotonation. Its nucleophilicity is influenced by the solvent in which it is dissolved. Understanding the properties of methoxide, including its charge and basicity, is crucial for predicting its behavior in different solvent environments and its effectiveness in nucleophilic reactions.
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Related Practice
Textbook Question
Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:
e. 1-bromo-2-butene + CH3O−
f. 1-bromo-2-butene + CH3OH
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Textbook Question
Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:
a. (R)-2-bromopentane+CH3O−
b. (R)-3-bromo-3-methylheptane+CH3OH
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Textbook Question
Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:
c. benzyl chloride + CH3CH2OH
d. allyl chloride + CH3OH
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Textbook Question
Alkylbenzyldimethyl ammonium chloride is a leave-on skin antiseptic used to treat such things as cuts and cold sores. It is also the antiseptic in many hand sanitizers. It is actually a mixture of compounds that differ in the number of carbons (any even number between 8 and 18) in the alkyl group. Show three different sets of reagents (each set composed of an alkyl chloride and an amine) that can be used to synthesize the alkylbenzyldimethyl ammonium chloride shown here.
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Textbook Question
Fill in the squares in the following chemical equations:
c.
d.
1
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