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 40a
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 40aChapter 12, Problem 40a
Predict the major product of the following elimination reactions.
(a) 
Verified step by step guidance1
Identify the type of elimination reaction (E1 or E2) based on the reaction conditions. For example, if a strong base is present, it is likely an E2 reaction, whereas a weak base and a polar protic solvent suggest an E1 reaction.
Determine the structure of the starting material and locate the β-hydrogens (hydrogens on the carbon adjacent to the carbon bearing the leaving group). These β-hydrogens are necessary for the elimination process.
For an E2 reaction, consider the anti-periplanar geometry requirement. The β-hydrogen and the leaving group must be in opposite planes (180° apart) for the elimination to occur. Draw the Newman projection if needed to confirm this geometry.
For an E1 reaction, the first step is the formation of a carbocation intermediate after the leaving group departs. Assess the stability of the carbocation and consider any possible rearrangements (e.g., hydride or alkyl shifts) to form a more stable carbocation.
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 usually the major product. Draw the possible alkene products and identify the most substituted one as the major product.
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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. Understanding the mechanism of elimination reactions, such as E1 and E2 pathways, is crucial for predicting the major products formed.
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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 this rule helps in predicting the outcome of elimination reactions, especially when multiple alkene products are possible.
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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 the stability of the resulting double bond. 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
Predict the major product of the following elimination reactions.
(b)
Textbook Question
Besides PBr3. and SOCl2 , there are other ways of synthesizing haloalkanes. One such way is shown. Provide an arrow-pushing mechanism that rationalizes formation of the chloroalkane. [Hint: Dimethyl sulfide is a good nucleophile and Cl₂ is an electrophile. Start by reacting those two together.]
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Textbook Question
Predict which side of the equilibrium is favored by ∆H, ∆G, and ∆S.
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