Textbook Question
Allylic halides have the structure
c. Show the products expected from SN1 solvolysis of these halides in ethanol.
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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 41b(i,ii)
Allylic halides have the structure
b. Draw the resonance structures of the allylic cations formed by ionization of the following halides.
(i) 
(ii) 
Verified step by step guidance1
Identify the allylic position in the given halides. The allylic position is the carbon atom adjacent to the carbon-carbon double bond.
For compound (i), remove the bromine atom to form a carbocation at the allylic position. This will result in a positive charge on the carbon atom adjacent to the double bond.
Draw the first resonance structure for compound (i) by moving the pi electrons from the double bond to form a new double bond with the carbocation, shifting the positive charge to the other end of the original double bond.
For compound (ii), similarly, remove the bromine atom to form a carbocation at the allylic position, resulting in a positive charge on the carbon atom adjacent to the double bond.
Draw the first resonance structure for compound (ii) by moving the pi electrons from the double bond to form a new double bond with the carbocation, shifting the positive charge to the other end of the original double bond.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Allylic Halides
Allylic halides are organic compounds where a halogen atom is bonded to a carbon atom adjacent to a carbon-carbon double bond. This structure allows for unique reactivity due to the presence of the double bond, which can stabilize intermediates through resonance. The allylic position is particularly reactive in substitution and elimination reactions.
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Resonance Structures
Resonance structures are different Lewis structures for a molecule that depict the same arrangement of atoms but differ in the distribution of electrons. They are used to represent the delocalization of electrons within a molecule, which can stabilize charged intermediates like allylic cations. Resonance structures are crucial for understanding the stability and reactivity of organic compounds.
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Allylic Cations
Allylic cations are positively charged intermediates formed when a halide ion leaves an allylic halide, resulting in a carbocation at the allylic position. These cations are stabilized by resonance, as the positive charge can be delocalized over the adjacent double bond. This delocalization makes allylic cations more stable than typical carbocations, influencing their reactivity in chemical reactions.
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Related Practice
Textbook Question
Two of the carbocations in Problem 6-42 are prone to rearrangement. Show how they might rearrange to more stable carbocations.
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Textbook Question
Allylic halides have the structure
a. Show how the first-order ionization of an allylic halide leads to a resonance-stabilized cation.
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Textbook Question
Give the substitution products expected from solvolysis of each compound by heating in ethanol.
(c)
(d)
Textbook Question
Give the substitution products expected from solvolysis of each compound by heating in ethanol.
(a)
(b)
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Textbook Question
List the following carbocations in decreasing order of their stability.
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