Textbook Question
Which substitution reaction takes place more rapidly?
d. CH3CH2Cl + I− or CH3CH2Br + I−
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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 15c,d
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 15c,dChapter 10, Problem 15c,d
What is the product of the reaction of bromoethane with each of the following nucleophiles?
c. (CH3)3N
d. CH3CH2S-
Verified step by step guidance1
Step 1: Identify the type of reaction. Bromoethane (C2H5Br) is a primary alkyl halide, and the reaction with nucleophiles typically proceeds via an SN2 mechanism due to the unhindered nature of the carbon attached to the bromine atom.
Step 2: Analyze the nucleophile in part (c). The nucleophile is trimethylamine ((CH3)3N), which is a neutral nucleophile with a lone pair of electrons on the nitrogen atom. In this case, the reaction will likely result in the formation of a quaternary ammonium salt through nucleophilic substitution.
Step 3: Write the reaction for part (c). The nitrogen in (CH3)3N attacks the carbon bonded to the bromine in bromoethane, displacing the bromide ion (Br⁻) and forming a quaternary ammonium salt: [(CH3)3N⁺CH2CH3]Br⁻.
Step 4: Analyze the nucleophile in part (d). The nucleophile is ethanethiolate (CH3CH2S⁻), which is a strong nucleophile due to the negatively charged sulfur atom. This nucleophile will also undergo an SN2 reaction with bromoethane.
Step 5: Write the reaction for part (d). The sulfur atom in CH3CH2S⁻ attacks the carbon bonded to the bromine in bromoethane, displacing the bromide ion (Br⁻) and forming the product CH3CH2SCH2CH3 (ethyl ethyl sulfide).
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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. Strong nucleophiles, such as thiolates or amines, are more likely to react with electrophiles like bromoethane. The strength of a nucleophile is influenced by factors such as charge, electronegativity, and steric hindrance.
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Nucleophilic Addition
Substitution Reactions
Substitution reactions involve the replacement of one functional group in a molecule with another. In the case of bromoethane, nucleophiles can perform either an SN1 or SN2 mechanism, depending on their structure and the conditions. Understanding these mechanisms is crucial for predicting the products of the reaction.
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Steric Hindrance
Steric hindrance refers to the prevention of reactions due to the spatial arrangement of atoms within a molecule. In nucleophilic substitution, bulky nucleophiles like (CH3)3N may experience steric hindrance, affecting their ability to approach and react with the electrophile. This concept is essential for determining the reaction pathway and product formation.
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Related Practice
Textbook Question
Draw the stereoisomers that are formed from the following SN1 reactions:
a. 3-bromo-3-methylpentane and methanol
b. 3-chloro-3-methylhexane and methanol
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Textbook Question
What is the product of the reaction of bromoethane with each of the following nucleophiles?
a. CH3CH2CH2O−
b. CH3C≡C−
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Textbook Question
Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide with azide ion (-N3), followed by catalytic hydrogenation. (Hint: An alkyl azide is not nucleophilic.)
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Textbook Question
Which substitution reaction takes place more rapidly?
c.
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Textbook Question
Explain why the reaction of an alkyl halide with ammonia gives a low yield of primary amine.
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