Textbook Question
Predict the major products of the following substitutions.
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Ch.6 - Alkyl Halides; Nucleophilic Substitution
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 6, Problem 14b
Predict the major products of the following substitutions.
b. 
Verified step by step guidance1
Identify the type of reaction: This is a nucleophilic substitution reaction where sodium acetylide (HC≡C:- Na+) acts as a nucleophile, and 1-chlorobutane (CH3CH2CH2CH2Cl) is the alkyl halide.
Determine the mechanism: Since 1-chlorobutane is a primary alkyl halide, the reaction will proceed via the SN2 mechanism. In an SN2 reaction, the nucleophile attacks the electrophilic carbon directly, leading to a one-step displacement of the leaving group (Cl⁻).
Analyze the nucleophile: Sodium acetylide (HC≡C:- Na+) is a strong nucleophile due to the negatively charged carbon in the acetylide ion. This makes it highly reactive toward electrophilic carbons.
Describe the reaction: The acetylide ion (HC≡C:-) will attack the carbon atom bonded to the chlorine in 1-chlorobutane (CH3CH2CH2CH2Cl). This results in the displacement of the chloride ion (Cl⁻) and the formation of a new carbon-carbon bond between the acetylide ion and the butyl group.
Write the product: The major product will be a terminal alkyne with the structure HC≡C-CH2CH2CH2CH3, where the acetylide ion has replaced the chlorine atom in 1-chlorobutane.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In this case, sodium acetylide (HC≡C:- Na+) acts as the nucleophile, targeting the carbon atom bonded to the chlorine in 1-chlorobutane. Understanding the mechanism of this reaction, whether it follows an SN1 or SN2 pathway, is crucial for predicting the major products.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Alkyne Reactivity
Alkynes, such as sodium acetylide, are highly reactive due to the presence of a triple bond, which can participate in various reactions, including nucleophilic substitutions. The terminal alkyne (HC≡C:-) has a negative charge on the carbon, making it a strong nucleophile. Recognizing the reactivity of alkynes helps in predicting how they will interact with alkyl halides like 1-chlorobutane.
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Leaving Groups
A leaving group is an atom or group that can depart from the parent molecule during a chemical reaction, facilitating the formation of new bonds. In the context of the reaction with 1-chlorobutane, the chloride ion (Cl-) is the leaving group. The stability of the leaving group significantly influences the reaction's rate and the formation of products, making it essential to consider when predicting the outcome of nucleophilic substitutions.
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Related Practice
Textbook Question
Predict the major products of the following substitutions.
e. 1-chloropentane + NaI →
Textbook Question
Predict the major products of the following substitutions.
d. CH3CH2CH2I + NaCN →
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Textbook Question
Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second.
c. Show another SN2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces 1-methoxybutane.
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Textbook Question
Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, and the products. Note that the initial product is the salt of an amine (RNH3+Br−), which is deprotonated by the excess ammonia to give the amine.
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Textbook Question
Predict the major products of the following substitutions.
a.
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