Textbook Question
Predict the products formed by sodium hydroxide-promoted dehydrohalogenation of the following compounds. In each case, predict which will be the major product.
d. cis-1-bromo-2-methylcyclohexane
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Ch. 7 - Structure and Synthesis of Alkenes; Elimination
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 7, Problem 50e
Predict the products formed by sodium hydroxide-promoted dehydrohalogenation of the following compounds. In each case, predict which will be the major product.
e. trans-1-bromo-2-methylcyclohexane
Verified step by step guidance1
Identify the type of reaction: Sodium hydroxide (NaOH) is a strong base, and the reaction involves dehydrohalogenation, which is an elimination reaction (E2 mechanism). This means a β-hydrogen will be removed along with the halogen (bromine) to form a double bond.
Locate the β-hydrogens: In trans-1-bromo-2-methylcyclohexane, the bromine atom is attached to carbon-1. The β-hydrogens are located on the carbons adjacent to carbon-1 (i.e., carbon-2 and carbon-6).
Determine the stereochemistry: Since the compound is trans, the β-hydrogen and the bromine atom must be anti-periplanar (in opposite planes) for the E2 elimination to occur. Analyze the chair conformation of the cyclohexane ring to identify which β-hydrogen satisfies this condition.
Predict the possible products: Removing a β-hydrogen from carbon-2 or carbon-6 will result in the formation of a double bond. This will lead to the formation of two possible alkenes: one with the double bond between carbon-1 and carbon-2, and the other with the double bond between carbon-1 and carbon-6.
Determine the major product: According to Zaitsev's rule, the more substituted alkene (the one with more alkyl groups attached to the double-bonded carbons) is typically the major product. Compare the substitution patterns of the two possible alkenes to predict the major product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dehydrohalogenation
Dehydrohalogenation is an elimination reaction where a hydrogen halide (HX) is removed from a molecule, typically resulting in the formation of a double bond. In the context of organic chemistry, this reaction often occurs in the presence of a strong base, such as sodium hydroxide, which abstracts a proton from the carbon adjacent to the halogen, leading to the formation of alkenes.
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03:02
The dehydrohalogenation mechanism.
Zaitsev's Rule
Zaitsev's Rule states that in elimination reactions, the more substituted alkene is generally the major product. This is because more substituted alkenes are more stable due to hyperconjugation and the inductive effect. Understanding this rule is crucial for predicting the major product in dehydrohalogenation reactions, especially when multiple elimination products are possible.
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01:18Defining Zaitsev’s Rule
Stereochemistry of Alkenes
Stereochemistry refers to the spatial arrangement of atoms in molecules and is particularly important in the formation of alkenes. In the case of trans-1-bromo-2-methylcyclohexane, the stereochemical configuration will influence the stability and formation of the alkene product. The formation of cis or trans alkenes can affect their reactivity and physical properties, making it essential to consider stereochemistry when predicting products.
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Related Practice
Textbook Question
Predict the products formed by sodium hydroxide-promoted dehydrohalogenation of the following compounds. In each case, predict which will be the major product.
a. 1-bromobutane
b. 2-chlorobutane
c. 3-bromopentane
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Textbook Question
What halides would undergo E2 dehydrohalogenation to give the following pure alkenes?
d. methylenecyclohexane
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Textbook Question
Predict the products of E1 elimination of the following compounds. Label the major products.
(c)
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Textbook Question
What halides would undergo E2 dehydrohalogenation to give the following pure alkenes?
e. 4-methylcyclohexene
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Textbook Question
What halides would undergo E2 dehydrohalogenation to give the following pure alkenes?
a. hex-1-ene
b. isobutylene
c. pent-2-ene
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