Textbook Question
How many allylic substituted bromoalkenes are formed from the reactions in Problems 18 if stereoisomers are included?
1181
views
Ch. 12 - Radicals
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
Chapter 13, Problem 19
How many allylic substituted bromoalkenes are formed from the reactions in Problems 17 if stereoisomers are included?
Verified step by step guidance1
Step 1: Analyze the given reaction conditions. The reaction involves NBS (N-bromosuccinimide) in the presence of heat (Δ) and peroxide. This is a radical bromination reaction that selectively brominates allylic positions in alkenes.
Step 2: Identify the allylic positions in the given molecule. Allylic positions are the carbon atoms adjacent to the double bond. In the provided structure, there are two allylic positions on either side of the double bond.
Step 3: Consider the possible products formed by bromination at each allylic position. Bromination at each allylic position can lead to different regioisomers, depending on which allylic hydrogen is replaced by bromine.
Step 4: Account for stereoisomers. Since the allylic carbons are sp3 hybridized, bromination can lead to stereoisomers (R and S configurations) at each brominated position. This increases the number of possible products.
Step 5: Combine regioisomeric and stereoisomeric possibilities. For each allylic position, consider the number of stereoisomers formed. Add these together to determine the total number of allylic substituted bromoalkenes formed.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Allylic Substitution
Allylic substitution refers to the replacement of a hydrogen atom at the allylic position (the carbon adjacent to a double bond) with another atom or group. This reaction is significant in organic chemistry as it allows for the formation of new compounds with varied properties. The presence of a double bond influences the reactivity and stability of the intermediates formed during the reaction.
Recommended video:
Guided course
00:48
The products of Allylic Chlorination.
Bromination with NBS
N-Bromosuccinimide (NBS) is a reagent commonly used for allylic bromination. It generates bromine radicals under specific conditions, such as heat or light, which can abstract hydrogen atoms from the allylic position, leading to the formation of allylic bromides. This method is advantageous because it selectively brominates the allylic position while minimizing the formation of other byproducts.
Recommended video:
Guided course
00:54Mechanism of Allylic Bromination.
Stereoisomerism
Stereoisomerism occurs when compounds have the same molecular formula and connectivity but differ in the spatial arrangement of their atoms. In the context of allylic bromination, the formation of stereoisomers is crucial as different configurations (cis/trans or E/Z) can arise from the reaction. Understanding stereoisomerism is essential for predicting the number of distinct products formed in a reaction, especially when multiple chiral centers are involved.
Recommended video:
Guided course
01:58Determining when molecules are stereoisomers.
Related Practice
Textbook Question
What hydrocarbon with the same molecular formula as in part a forms three monochlorinated products? One is achiral and two are chiral.
1103
views
Textbook Question
Two products are formed when methylenecyclohexane reacts with NBS? Show how each is formed. Disregard stereoisomers.
1673
views
Textbook Question
How many stereoisomers are formed from the reaction of cyclohexene with NBS?
991
views
Textbook Question
How many stereoisomers are formed from the reaction of 3-methylcyclohexene with NBS?
1094
views
Textbook Question
What hydrocarbon with molecular formula C4H10 forms only two monochlorinated products? Both products are achiral.
1576
views