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'Show the mechanism by pushing arrows to show how you came up with your structure: OH Br HBr

'Show the mechanism by pushing arrows to show how you came up with your structure: OH Br HBr

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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### Mechanism of Alcohol to Alkyl Bromide Conversion Using HBr To understand the transformation of an alcohol to an alkyl bromide using hydrobromic acid (HBr), let's consider the following reaction: #### Reaction Overview - **Reactant:** A cyclohexane ring with a hydroxyl group (-OH) attached to a carbon, and an ethyl group branching from the adjacent carbon. - **Reagent:** Hydrobromic acid (HBr) - **Product:** A cyclohexane ring with a bromine (Br) atom attached at the same carbon where the hydroxyl group was originally, and an ethyl group on the adjacent carbon. #### Step-by-Step Mechanism 1. **Protonation of the Alcohol:** The lone pair of electrons on the oxygen atom of the hydroxyl group can attack a proton (H⁺) from HBr, resulting in the protonation of the hydroxyl group. This transforms the hydroxyl group (-OH) into a better leaving group – water (H₂O). 2. **Formation of a Carbocation:** The protonated alcohol (now a water molecule) leaves, creating a positively charged carbocation on the carbon where the hydroxyl group was originally attached. 3. **Nucleophilic Attack:** The bromide ion (Br⁻) generated from the dissociation of HBr attacks the carbocation, resulting in the substitution of the hydroxyl group with a bromine atom. #### Visual Explanation - **Initial Structure:** The starting molecule features a cyclohexane ring with a hydroxyl group attached to one carbon (showing OH) and an ethyl group on the adjacent carbon. - **Intermediate Step:** The intermediate structure includes a protonated alcohol, which will then leave as water, resulting in a carbocation formation at that carbon position. - **Final Structure:** The resulting molecule after the nucleophilic attack by Br⁻ shows the cyclohexane ring with a bromine atom at the same position where the hydroxyl group was initially, alongside the ethyl group on the adjacent carbon. This detailed mechanism helps in understanding the transformation process of converting alcohols to alkyl bromides via the use of acidic conditions provided by HBr.
Transcribed Image Text:### Mechanism of Alcohol to Alkyl Bromide Conversion Using HBr To understand the transformation of an alcohol to an alkyl bromide using hydrobromic acid (HBr), let's consider the following reaction: #### Reaction Overview - **Reactant:** A cyclohexane ring with a hydroxyl group (-OH) attached to a carbon, and an ethyl group branching from the adjacent carbon. - **Reagent:** Hydrobromic acid (HBr) - **Product:** A cyclohexane ring with a bromine (Br) atom attached at the same carbon where the hydroxyl group was originally, and an ethyl group on the adjacent carbon. #### Step-by-Step Mechanism 1. **Protonation of the Alcohol:** The lone pair of electrons on the oxygen atom of the hydroxyl group can attack a proton (H⁺) from HBr, resulting in the protonation of the hydroxyl group. This transforms the hydroxyl group (-OH) into a better leaving group – water (H₂O). 2. **Formation of a Carbocation:** The protonated alcohol (now a water molecule) leaves, creating a positively charged carbocation on the carbon where the hydroxyl group was originally attached. 3. **Nucleophilic Attack:** The bromide ion (Br⁻) generated from the dissociation of HBr attacks the carbocation, resulting in the substitution of the hydroxyl group with a bromine atom. #### Visual Explanation - **Initial Structure:** The starting molecule features a cyclohexane ring with a hydroxyl group attached to one carbon (showing OH) and an ethyl group on the adjacent carbon. - **Intermediate Step:** The intermediate structure includes a protonated alcohol, which will then leave as water, resulting in a carbocation formation at that carbon position. - **Final Structure:** The resulting molecule after the nucleophilic attack by Br⁻ shows the cyclohexane ring with a bromine atom at the same position where the hydroxyl group was initially, alongside the ethyl group on the adjacent carbon. This detailed mechanism helps in understanding the transformation process of converting alcohols to alkyl bromides via the use of acidic conditions provided by HBr.
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