Textbook Question
Predict the products of the following SN2 reactions.
(e)
(f)
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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 46c
Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.
(c) 
Verified step by step guidance1
Step 1: Begin with cyclohexane as the starting material. Cyclohexane is a saturated hydrocarbon with no functional groups, so the first step is to introduce a functional group that can be further modified.
Step 2: Perform a free radical halogenation reaction using bromine (Br₂) and light (hv) to introduce a bromine atom onto the cyclohexane ring. This will yield bromocyclohexane.
Step 3: Convert bromocyclohexane into cyclohexyl cyanide by performing a nucleophilic substitution reaction (SN2). Use sodium cyanide (NaCN) as the nucleophile in an appropriate solvent, such as DMSO, to replace the bromine atom with a cyano group (-CN).
Step 4: Ensure the reaction conditions are optimized for SN2 substitution, as steric hindrance in cyclohexane is minimal, allowing for efficient substitution.
Step 5: Purify the product, cyclohexyl cyanide, using standard organic purification techniques such as distillation or recrystallization, depending on the physical properties of the compound.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Cyclohexane Structure
Cyclohexane is a six-membered carbon ring with the molecular formula C6H12. It is a saturated hydrocarbon, meaning it contains only single bonds between carbon atoms. Understanding its structure is crucial for predicting reactivity and the types of reactions it can undergo, such as substitution or elimination.
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Drawing Resonance Structures
Nucleophilic Substitution Reactions
Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule with a nucleophile. In the context of cyclohexane, the introduction of a cyanide group (CN) typically occurs through a nucleophilic substitution mechanism, where the nucleophile attacks a carbon atom, leading to the formation of a new bond.
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Functional Group Transformation
Functional group transformation refers to the process of converting one functional group into another within a molecule. In this case, transforming cyclohexane into a compound with a cyanide group involves understanding how to manipulate the existing structure to introduce new functional groups, which is essential for synthesizing desired organic compounds.
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Related Practice
Textbook Question
Predict the products of the following SN2 reactions.
(c)
(d)
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Textbook Question
A solution of pure (S)-2-iodobutane ([α] = +15.90°) in acetone is allowed to react with radioactive iodide, 131I–, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°.
a. Determine the percentages of (R)- and (S)-2-iodobutane in the product mixture.
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Textbook Question
Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.
(e)
1077
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Textbook Question
Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.
(a)
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Textbook Question
Strawberry growers have used large quantities of methyl bromide (b.p. 4 °C) to sterilize the soil before planting their crops. Like some of the freons, methyl bromide can diffuse up into the stratosphere, where it damages the protective ozone layer. Agricultural chemists have suggested using methyl iodide (b.p. 43 °C) as a replacement for methyl bromide. Why is methyl iodide likely to be more toxic to agricultural pests (and people) than methyl bromide? Why is methyl iodide less likely to reach the stratosphere than methyl bromide?
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