Textbook Question
Predict the major product of the following elimination reactions.
(c)
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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 40b
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 40bChapter 12, Problem 40b
Predict the major product of the following elimination reactions.
(b) 
Verified step by step guidance1
Step 1: Identify the type of elimination reaction (E1 or E2). This depends on the reaction conditions, such as the presence of a strong base (favoring E2) or a weak base and polar protic solvent (favoring E1). Analyze the given reaction conditions to determine the mechanism.
Step 2: Locate the β-hydrogens on the carbon atoms adjacent to the carbon bearing the leaving group. These β-hydrogens are potential candidates for elimination.
Step 3: Apply Zaitsev's rule, which states that the major product of an elimination reaction is typically the more substituted alkene. This means the double bond will form between the carbon atoms that result in the most stable alkene.
Step 4: Consider steric hindrance and the base used. If the base is bulky, it may favor the formation of the less substituted alkene (Hofmann product) due to steric hindrance.
Step 5: Draw the possible products and identify the major product based on the stability of the alkenes formed (more substituted alkenes are generally more stable).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Elimination Reactions
Elimination reactions are a type of organic reaction where two substituents are removed from a molecule, resulting in the formation of a double bond or a ring structure. These reactions typically involve the loss of a leaving group and a hydrogen atom from adjacent carbon atoms, leading to alkenes or alkynes as products. Understanding the mechanism and conditions that favor elimination is crucial for predicting the major products.
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Recognizing Elimination Reactions.
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. Recognizing the stability of potential alkene products helps in predicting which product will dominate in elimination reactions.
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Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In elimination reactions, regioselectivity is influenced by factors such as sterics and electronic effects, which determine the most favorable pathway for the reaction. Understanding regioselectivity is essential for accurately predicting the major product in elimination reactions.
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Related Practice
Textbook Question
When HCl was used for the attempted dehydration reaction shown, a reaction occurred, but none of the desired product was formed. Suggest the identity of the actual product obtained.
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Textbook Question
Identify the alcohol(s) that would produce the following alkenes under the given conditions.
(a)
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Textbook Question
Identify the alcohol(s) that would produce the following alkenes under the given conditions.
(b)
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Textbook Question
Predict the major product of the following elimination reactions.
(a)
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Textbook Question
Predict which side of the equilibrium is favored by ∆H, ∆G, and ∆S.
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