Textbook Question
Draw the product of each of the following reactions:
2.
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Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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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
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Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 119c
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 119cChapter 10, Problem 119c
cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO−.
c. How many stereoisomers does each of the elimination and substitution reactions form?
Verified step by step guidance1
Step 1: Analyze the elimination reaction. In an elimination reaction, the hydroxide ion (HO⁻) acts as a base and removes a proton from a β-carbon, leading to the formation of a double bond. Both cis-4-bromocyclohexanol and trans-4-bromocyclohexanol undergo elimination to form the same alkene product because the stereochemistry of the starting material does not affect the planar nature of the double bond formed.
Step 2: Determine the stereoisomers formed in the elimination reaction. Since the elimination product is an alkene, check for the possibility of cis/trans (E/Z) isomerism in the double bond. If the double bond is formed in a way that allows for stereoisomerism, count the possible configurations.
Step 3: Analyze the substitution reaction. In a substitution reaction, the hydroxide ion (HO⁻) acts as a nucleophile and replaces the bromine atom. The stereochemistry of the starting material affects the stereochemistry of the substitution product, leading to different stereoisomers for cis-4-bromocyclohexanol and trans-4-bromocyclohexanol.
Step 4: Determine the stereoisomers formed in the substitution reaction. For each starting material, consider the stereochemical outcome of the nucleophilic substitution (SN2 mechanism). The inversion of configuration at the carbon bearing the bromine atom will lead to different stereoisomers.
Step 5: Summarize the stereoisomers. Count the total number of stereoisomers formed in both the elimination and substitution reactions for cis-4-bromocyclohexanol and trans-4-bromocyclohexanol, considering the stereochemical differences in the substitution products and the potential stereoisomerism in the elimination product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stereoisomerism
Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This can lead to different physical and chemical properties. In the context of the question, cis and trans isomers of 4-bromocyclohexanol exhibit stereoisomerism, affecting the products formed during elimination and substitution reactions.
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Elimination vs. Substitution Reactions
Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double bond or a ring structure. In contrast, substitution reactions involve replacing one atom or group in a molecule with another. Understanding these mechanisms is crucial for predicting the products formed from cis- and trans-4-bromocyclohexanol when reacted with HO−.
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Regioselectivity and Stereoselectivity
Regioselectivity refers to the preference of a chemical reaction to occur at one site over another in a molecule, while stereoselectivity indicates the preference for forming one stereoisomer over another. In the reactions of cis- and trans-4-bromocyclohexanol, the different spatial arrangements lead to distinct regio- and stereoselective outcomes, influencing the number of stereoisomers produced in both elimination and substitution reactions.
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Related Practice
Textbook Question
Draw the product of each of the following reactions:
1.
2
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Textbook Question
How could you prepare the following compounds from the given starting materials?
b.
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Textbook Question
cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO−.
a. Why do they form the same elimination product?
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Textbook Question
cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO−.
b. Explain, by showing the mechanisms, why different substitution products are obtained.
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Textbook Question
Give two sets of reactants (each set including an alkyl halide and a nucleophile) that could be used to synthesize the following alkyne:
CH3CH2C≡CCH2CH2CH2CH3
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