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 14d
Predict the major products of the following substitutions.
d. CH3CH2CH2I + NaCN →
Verified step by step guidance1
Identify the type of substitution reaction: The reaction involves CH3CH2CH2I (1-iodopropane) and NaCN (sodium cyanide). This is a nucleophilic substitution reaction, specifically SN2, because the substrate is a primary alkyl halide, which favors the SN2 mechanism.
Understand the mechanism: In an SN2 reaction, the nucleophile (CN⁻ from NaCN) attacks the electrophilic carbon (the carbon attached to the iodine atom) from the opposite side of the leaving group (I⁻). This results in a single-step, concerted mechanism with inversion of configuration at the carbon center.
Determine the nucleophile and leaving group: The nucleophile is CN⁻, which is a strong nucleophile, and the leaving group is I⁻, which is a good leaving group due to its large size and ability to stabilize the negative charge.
Predict the product: The CN⁻ nucleophile will replace the iodine atom in the substrate, forming a new carbon-carbon bond. The product will be CH3CH2CH2CN (butanenitrile), where the cyanide group (-CN) is attached to the terminal carbon of the original alkyl halide.
Verify the reaction conditions: Ensure that the reaction is carried out in a polar aprotic solvent (e.g., DMSO or acetone) to favor the SN2 mechanism and avoid side reactions.
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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 replaces a leaving group in a molecule. In this case, NaCN acts as the nucleophile, attacking the carbon atom bonded to the iodine in CH3CH2CH2I. Understanding the mechanism, whether it follows an SN1 or SN2 pathway, is crucial for predicting the product.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Leaving Groups
A leaving group is an atom or group that can depart from the parent molecule during a chemical reaction. In this reaction, iodine (I) is the leaving group, and its ability to leave is influenced by its bond strength and stability as an ion. A good leaving group enhances the likelihood of a successful nucleophilic substitution.
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07:22The 3 important leaving groups to know.
Stereochemistry of Substitution Reactions
Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In nucleophilic substitution reactions, the stereochemistry can change depending on whether the reaction proceeds via an SN1 or SN2 mechanism. This is important for predicting the configuration of the product, especially if the substrate is chiral.
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Related Practice
Textbook Question
When methylenecyclohexane is treated with a low concentration of bromine under irradiation by a sunlamp, two substitution products are formed.
a. Propose structures for these two products. (b) Propose a mechanism to account for their formation.
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Textbook Question
Predict the major products of the following substitutions.
b.
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Textbook Question
Predict the major products of the following substitutions.
e. 1-chloropentane + NaI →
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
Predict the major products of the following substitutions.
a.
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