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Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Reaction: 1° Alcohol to Alkyl Halide (S<sub>N</sub>2)** **Substitution Reaction:** **Mechanism:** This reaction illustrates the conversion of a primary alcohol to an alkyl halide using hydrochloric acid (HCl). **Reactant:** - **Structure:** \[ \text{CH}_3\text{-CH}_2\text{-OH} \] **Reagent:** - **HCl** **Product:** - **Structure:** \[ \text{CH}_3\text{-CH}_2\text{-Cl} \] The mechanism follows an S<sub>N</sub>2 pathway, where the hydroxyl group (-OH) in the alcohol is replaced by the chlorine atom from HCl, forming the alkyl chloride.
Transcribed Image Text:**Reaction: 1° Alcohol to Alkyl Halide (S<sub>N</sub>2)** **Substitution Reaction:** **Mechanism:** This reaction illustrates the conversion of a primary alcohol to an alkyl halide using hydrochloric acid (HCl). **Reactant:** - **Structure:** \[ \text{CH}_3\text{-CH}_2\text{-OH} \] **Reagent:** - **HCl** **Product:** - **Structure:** \[ \text{CH}_3\text{-CH}_2\text{-Cl} \] The mechanism follows an S<sub>N</sub>2 pathway, where the hydroxyl group (-OH) in the alcohol is replaced by the chlorine atom from HCl, forming the alkyl chloride.
**Reaction Overview:** The image illustrates a chemical reaction where a secondary alcohol is treated with hydrochloric acid (HCl), resulting in the formation of a tertiary alkyl halide. **Reactants and Product:** - **Starting Material:** The structure shown is a cyclopentyl secondary alcohol. This alcohol has a hydroxyl group (OH) attached to a carbon atom that is also bonded to two other carbon atoms, making it a secondary alcohol. - **Reagent:** Hydrochloric acid (HCl) is used in the reaction. - **Product:** The product is a cyclopentyl chloride, a tertiary alkyl halide, where the hydroxyl group has been replaced by a chlorine atom. **Key Concept:** - **Carbocation Rearrangement:** The transformation involves a carbocation intermediate. In the presence of HCl, the hydroxyl group is protonated and removed as a water molecule, forming a carbocation. A hydride shift occurs, where a hydrogen atom with a pair of electrons moves from an adjacent carbon to stabilize the carbocation, leading to a more substituted (tertiary) carbocation. This tertiary carbocation is then attacked by the chloride ion, resulting in the formation of a tertiary alkyl halide. **Educational Explanation:** This reaction demonstrates the principles of carbocation stability and rearrangement in organic chemistry. Tertiary carbocations are more stable than secondary ones due to greater alkyl substitution, which offers more hyperconjugation and inductive effects to stabilize the positive charge. Therefore, even though the starting alcohol is secondary, the reaction conditions favor the formation of a tertiary carbocation and subsequent substitution to form a tertiary alkyl halide.
Transcribed Image Text:**Reaction Overview:** The image illustrates a chemical reaction where a secondary alcohol is treated with hydrochloric acid (HCl), resulting in the formation of a tertiary alkyl halide. **Reactants and Product:** - **Starting Material:** The structure shown is a cyclopentyl secondary alcohol. This alcohol has a hydroxyl group (OH) attached to a carbon atom that is also bonded to two other carbon atoms, making it a secondary alcohol. - **Reagent:** Hydrochloric acid (HCl) is used in the reaction. - **Product:** The product is a cyclopentyl chloride, a tertiary alkyl halide, where the hydroxyl group has been replaced by a chlorine atom. **Key Concept:** - **Carbocation Rearrangement:** The transformation involves a carbocation intermediate. In the presence of HCl, the hydroxyl group is protonated and removed as a water molecule, forming a carbocation. A hydride shift occurs, where a hydrogen atom with a pair of electrons moves from an adjacent carbon to stabilize the carbocation, leading to a more substituted (tertiary) carbocation. This tertiary carbocation is then attacked by the chloride ion, resulting in the formation of a tertiary alkyl halide. **Educational Explanation:** This reaction demonstrates the principles of carbocation stability and rearrangement in organic chemistry. Tertiary carbocations are more stable than secondary ones due to greater alkyl substitution, which offers more hyperconjugation and inductive effects to stabilize the positive charge. Therefore, even though the starting alcohol is secondary, the reaction conditions favor the formation of a tertiary carbocation and subsequent substitution to form a tertiary alkyl halide.
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