Textbook Question
What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?
g.
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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 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 HalidesProblem 70h
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 70hChapter 9, Problem 70h
What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?
h. 
Verified step by step guidance1
Step 1: Analyze the given compound structure. The compound shown contains a nitrile group (-C≡N) attached to a butane chain. This indicates that the nucleophile used in the reaction must have introduced the nitrile group.
Step 2: Recall the mechanism of nucleophilic substitution reactions. 1-Iodobutane is a primary alkyl halide, which typically undergoes SN2 reactions. In an SN2 reaction, the nucleophile attacks the carbon bonded to the leaving group (iodine) in a single step, displacing the leaving group.
Step 3: Identify the nucleophile that can introduce the nitrile group. The nucleophile in this case would be the cyanide ion (CN⁻), as it contains the nitrile group and is a strong nucleophile capable of participating in an SN2 reaction.
Step 4: Write the reaction mechanism. The cyanide ion (CN⁻) attacks the carbon atom bonded to iodine in 1-iodobutane, forming a new bond between the carbon and the cyanide group while displacing iodine as the leaving group.
Step 5: Summarize the reaction. The nucleophile required to form the given compound from 1-iodobutane is the cyanide ion (CN⁻). The reaction proceeds via an SN2 mechanism, resulting in the substitution of the iodine atom with the nitrile group.
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3mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophiles
Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. They are typically negatively charged or neutral molecules with lone pairs of electrons. In the context of organic reactions, nucleophiles attack electrophiles, which are electron-deficient species. Common examples include hydroxide ions (OH⁻), alkoxides (RO⁻), and amines (RNH₂).
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Nucleophilic Addition
SN2 Reaction Mechanism
The SN2 (substitution nucleophilic bimolecular) reaction is a type of nucleophilic substitution where the nucleophile attacks the electrophile simultaneously as the leaving group departs. This mechanism involves a single concerted step, leading to the inversion of configuration at the carbon center. It is favored by primary and some secondary alkyl halides, such as 1-iodobutane, due to steric accessibility.
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08:33Drawing the SN2 Mechanism
Leaving Groups
Leaving groups are atoms or groups that can depart from the parent molecule during a chemical reaction, allowing for the formation of new bonds. A good leaving group is typically stable after departure, which is often the case for halides like iodide (I⁻). In SN2 reactions, the quality of the leaving group significantly influences the reaction rate, with better leaving groups facilitating faster reactions.
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07:22The 3 important leaving groups to know.
Related Practice
Textbook Question
What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?
e.
f.
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Textbook Question
Explain how each of the following changes affect the rate of the reaction of 1-bromobutane with ethoxide ion in DMF.
c. The alkyl halide is changed to 1-chlorobutane.
d. The alkyl halide is changed to 2-bromobutane.
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Textbook Question
What nucleophiles would form the following compounds as a result of reacting with 1-iodobutane?
a.
b.
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Textbook Question
Explain how the following changes affect the rate of the reaction of 2-bromo-2-methylbutane with methanol:
a. The alkyl halide is changed to 2-chloro-2-methylbutane.
b. The alkyl halide is changed to 2-chloro-3-methylbutane.
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Textbook Question
Explain how each of the following changes affect the rate of the reaction of 1-bromobutane with ethoxide ion in DMF.
a. The concentration of both the alkyl halide and the nucleophile are tripled.
b. The solvent is changed to ethanol.
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