Textbook Question
What is the major elimination product obtained from the reaction of each of the following alkyl halides with hydroxide ion?
c.
1572
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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 Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- 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 23a
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 23aChapter 10, Problem 23a
What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?
a. 
Verified step by step guidance1
Identify the alkyl halide structure and classify it as primary, secondary, or tertiary. This classification will help determine the likelihood of elimination (E2) versus substitution (SN2). For E2 reactions, secondary and tertiary alkyl halides are more favorable.
Recall the mechanism of an E2 reaction: it is a one-step concerted process where a strong base (in this case, hydroxide ion, OH⁻) abstracts a β-hydrogen, and the leaving group departs simultaneously, forming a double bond (alkene).
Locate the β-hydrogens on the carbon atoms adjacent to the carbon bearing the leaving group (halide). These β-hydrogens are the ones that can be abstracted by the hydroxide ion.
Apply Zaitsev's rule to predict the major product. Zaitsev's rule states that the more substituted alkene (the one with more alkyl groups attached to the double-bonded carbons) is generally the major product in an E2 reaction, as it is more stable.
Draw the possible elimination products by removing a β-hydrogen and the leaving group, forming double bonds in all possible locations. Identify the most substituted alkene as the major product, keeping in mind stereochemistry if applicable (e.g., trans alkenes are generally more stable than cis alkenes).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
E2 Reaction Mechanism
The E2 (bimolecular elimination) reaction is a concerted mechanism where a base abstracts a proton from a β-carbon while a leaving group departs from the α-carbon, resulting in the formation of a double bond. This reaction typically requires strong bases and occurs in a single step, making it essential to understand the stereochemistry and regioselectivity involved.
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Drawing the E2 Mechanism.
Alkyl Halides
Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (F, Cl, Br, I). The nature of the alkyl halide, including its structure (primary, secondary, or tertiary), significantly influences the outcome of elimination reactions, as steric hindrance and the stability of the resulting alkene play crucial roles in determining the major product.
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Regioselectivity in Elimination Reactions
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others. In E2 reactions, the more substituted alkene (Zaitsev's rule) is often favored due to its greater stability, but in some cases, less substituted alkenes may be produced (Hofmann elimination) depending on the sterics and the base used, making it important to analyze the specific alkyl halide.
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Related Practice
Textbook Question
What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?
b.
1122
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Textbook Question
Which of the following reactions take place more rapidly when the concentration of the nucleophile is increased?
767
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Textbook Question
What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?
e.
1483
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Textbook Question
What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?
c.
d.
823
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Textbook Question
What is the major elimination product obtained from the reaction of each of the following alkyl halides with hydroxide ion?
a.
b.
915
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