Textbook Question
The reaction of chloromethane with hydroxide ion at 30 °C has a ΔG° value of −21.7 kcal/mol. What is the equilibrium constant for the reaction?
1
views
Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 127b
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 127bChapter 10, Problem 127b
For each of the following compounds, draw the product that forms in an E2 reaction and indicate its configuration:
b. (1S,2R)-1-bromo-1,2-diphenylpropane
Verified step by step guidance1
Identify the substrate: The compound given is (1S,2R)-1-bromo-1,2-diphenylpropane. It contains a bromine atom on the first carbon, which is the leaving group, and two phenyl groups attached to the first and second carbons.
Understand the E2 mechanism: The E2 reaction is a one-step elimination process where a base abstracts a proton (β-hydrogen) from a β-carbon, and the leaving group (bromine) departs simultaneously, forming a double bond.
Locate the β-hydrogens: In this compound, the β-hydrogens are on the second carbon (C-2). Since the configuration is (1S,2R), the β-hydrogens are positioned such that one is anti-periplanar to the bromine atom on C-1. This anti-periplanar geometry is required for the E2 reaction to proceed.
Determine the product: The elimination of HBr will result in the formation of a double bond between C-1 and C-2. The configuration of the product will depend on the stereochemistry of the starting material and the anti-periplanar elimination. The major product will likely be the more stable (E)-alkene due to steric and electronic factors.
Draw the product and indicate its configuration: The product will be a double bond between C-1 and C-2, with the phenyl groups on opposite sides of the double bond (E-configuration). Ensure the stereochemistry is clearly indicated in the drawing.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
13mWas this helpful?
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 type of elimination reaction where a base removes 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 is characterized by a single concerted step, meaning that bond breaking and bond formation occur simultaneously. The stereochemistry of the reactants plays a crucial role in determining the configuration of the product.
Recommended video:
Guided course
09:36
Drawing the E2 Mechanism.
Stereochemistry and Configuration
Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of E2 reactions, the configuration of the starting material (R or S) influences the stereochemical outcome of the product. The E2 mechanism typically favors the formation of the more stable trans or E isomer, and understanding the stereochemical implications is essential for predicting the correct product configuration.
Recommended video:
1:38Polymer Stereochemistry Concept 1
Substituent Effects on Elimination Reactions
The presence of bulky substituents can significantly influence the outcome of E2 reactions. In the case of (1S,2R)-1-bromo-1,2-diphenylpropane, the two phenyl groups create steric hindrance that affects the accessibility of the β-hydrogens for elimination. This steric effect can lead to preferential formation of certain products based on the orientation of the substituents and the stability of the resulting alkene.
Recommended video:
Guided course
00:38Intro to Substitution/Elimination Problems
Related Practice
Textbook Question
When equivalent amounts of methyl bromide and sodium iodide are dissolved in methanol, the concentration of iodide ion quickly decreases and then slowly returns to its original concentration. Account for this observation.
2
views
Textbook Question
For each of the following compounds, draw the product that forms in an E2 reaction and indicate its configuration:
a. (1S,2S)-1-bromo-1,2-diphenylpropane
1
views
Textbook Question
What products are formed when the following stereoisomer of 2-chloro-1,3-dimethylcyclohexane reacts with methoxide ion?
2
views
Textbook Question
Predict the product for the following reaction and write a mechanism to explain how it is formed.
1
views
Textbook Question
Explain why the following alkyl halide does not undergo a substitution reaction, regardless of the base that is used.
1
views