Textbook Question
Predict the product of the following substitution reactions, paying close attention to the stereochemical outcome of the reactions.
(f)
1
views
Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Mullins 1st EditionCh. 12 - Substitution and Elimination: Reactions of HaloalkanesProblem 55c
Mullins 1st EditionCh. 12 - Substitution and Elimination: Reactions of HaloalkanesProblem 55cChapter 11, Problem 55c
Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.
(c) 
Verified step by step guidance1
Analyze the type of elimination reaction: Determine whether the reaction proceeds via an E1 or E2 mechanism. This depends on factors such as the strength of the base, the structure of the substrate (primary, secondary, or tertiary), and the reaction conditions (e.g., heat). For example, a strong base and a secondary or tertiary substrate often favor an E2 mechanism.
Identify the β-hydrogens: Locate the β-carbons (carbons adjacent to the carbon bearing the leaving group) and identify the β-hydrogens that can be eliminated. These hydrogens are crucial for forming the double bond in the elimination product.
Consider Zaitsev's rule: Predict the major product based on Zaitsev's rule, which states that the more substituted alkene (the one with more alkyl groups attached to the double-bonded carbons) is typically the major product. However, if a bulky base is used, the less substituted alkene (Hofmann product) may dominate.
Evaluate stereochemistry: For an E2 reaction, the β-hydrogen and the leaving group must be anti-periplanar (in the same plane but opposite sides). Draw the Newman projection or use a chair conformation (if applicable) to ensure proper alignment for elimination. This step determines the stereochemical outcome of the product.
Draw the major product(s): Based on the above analysis, draw the structure of the major alkene product(s), ensuring that the stereochemistry and substitution pattern are consistent with the mechanism and rules applied.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Elimination Reactions
Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double bond. The most common types are E1 and E2 mechanisms, where E1 is a two-step process involving carbocation formation, while E2 is a one-step concerted process. Understanding the mechanism is crucial for predicting the products and their stereochemistry.
Recommended video:
Guided course
00:40
Recognizing Elimination Reactions.
Stereochemistry
Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In elimination reactions, the stereochemical outcome can lead to different products, such as cis or trans isomers. Recognizing the stereochemical implications of the reaction mechanism is essential for predicting the major product.
Recommended video:
1:38Polymer Stereochemistry Concept 1
Zaitsev's Rule
Zaitsev's Rule states that in elimination reactions, the more substituted alkene is typically the major product. This principle helps predict the outcome of reactions by favoring the formation of more stable alkenes, which are generally more substituted. Understanding this rule aids in determining the preferred product in elimination scenarios.
Recommended video:
Guided course
01:18Defining Zaitsev’s Rule
Related Practice
Textbook Question
Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.
(d)
2
views
Textbook Question
Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.
(b)
1
views
Textbook Question
Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.
(f)
2
views
Textbook Question
Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.
(a)
7
views
Textbook Question
Predict the product(s) of the following substitution or elimination reactions, paying close attention to the stereochemical outcome of the reactions.
(a)
2
views