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What product is obtained when the following compound undergoes two successive elimination reactions?
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Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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 HalidesProblema 54
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblema 54Capitolo 9, Problema 54
Amines are good nucleophiles, even though they are neutral. How would the rate of an SN2 reaction between an amine and an alkyl halide be affected if the polarity of the solvent is increased?
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Understand the SN2 reaction mechanism: In an SN2 reaction, the nucleophile attacks the electrophilic carbon of the alkyl halide in a single, concerted step, displacing the leaving group. The rate of the reaction depends on the strength of the nucleophile and the nature of the solvent.
Recognize the role of amines as nucleophiles: Amines are good nucleophiles because the lone pair of electrons on the nitrogen atom can readily attack the electrophilic carbon. However, their nucleophilicity can be influenced by the solvent environment.
Consider the effect of solvent polarity: In an SN2 reaction, polar aprotic solvents (e.g., acetone, DMSO) are generally preferred because they do not solvate the nucleophile strongly, allowing it to remain reactive. Polar protic solvents (e.g., water, alcohols) can hydrogen bond with the nucleophile, reducing its nucleophilicity and slowing the reaction.
Analyze the impact of increasing solvent polarity: If the polarity of the solvent is increased, and the solvent is polar protic, the amine nucleophile will be more strongly solvated through hydrogen bonding. This reduces the availability of the lone pair on nitrogen for nucleophilic attack, thereby decreasing the rate of the SN2 reaction.
Conclude the relationship: The rate of the SN2 reaction between the amine and the alkyl halide will decrease if the polarity of the solvent is increased, provided the solvent is polar protic. If the solvent is polar aprotic, the effect on the rate may be less pronounced or negligible.
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Nucleophilicity
Nucleophilicity refers to the ability of a species to donate an electron pair to an electrophile, forming a chemical bond. Amines, despite being neutral, possess a lone pair of electrons on the nitrogen atom, making them effective nucleophiles. Their nucleophilicity can be influenced by factors such as steric hindrance and the solvent environment.
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Nucleophilic Addition
SN2 Reaction Mechanism
The SN2 (substitution nucleophilic bimolecular) reaction mechanism involves a single concerted step where the nucleophile attacks the electrophile, leading to the displacement of a leaving group. This mechanism is characterized by a transition state where both the nucleophile and the substrate are involved. The rate of an SN2 reaction is dependent on the concentration of both the nucleophile and the substrate.
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08:33Drawing the SN2 Mechanism
Solvent Polarity
Solvent polarity affects the solvation of reactants and transition states in a chemical reaction. In polar solvents, nucleophiles can be stabilized through solvation, which may reduce their reactivity. Increasing solvent polarity generally slows down SN2 reactions because it stabilizes the nucleophile, making it less available to attack the electrophile, thus decreasing the reaction rate.
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01:16Identification of polarity in solvents
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