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Propose a plausible mechanism for the following transformation: HO H [H3O*] EtoH

Propose a plausible mechanism for the following transformation: HO H [H3O*] EtoH

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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**Current Attempt in Progress** **Propose a plausible mechanism for the following transformation:** *Reactants:* - Starting material with a hydroxyl group (HO) on a carbon chain. - A carbonyl group with an aldehyde (CHO). *Reagents:* - Acid catalyst (\( \text{H}_3\text{O}^+ \)) - Ethanol (\( \text{EtOH} \)) *Product:* - Cyclic hemiacetal with an ether and an ethyl group. **19.55** ✔️ **Correct.** Formation of a hemiacetal follows a common pattern for mechanisms of acid-catalyzed reactions: Protonate, Attack, Deprotonate (P.A.D.). **The first three steps of the mechanism involve the formation of a hemiacetal.** - **The first step is** *protonation of the carbonyl oxygen atom.* - **The second step is** *nucleophilic attack.* - **The third step is** *deprotonation of a positively charged oxygen atom.*
Transcribed Image Text:**Current Attempt in Progress** **Propose a plausible mechanism for the following transformation:** *Reactants:* - Starting material with a hydroxyl group (HO) on a carbon chain. - A carbonyl group with an aldehyde (CHO). *Reagents:* - Acid catalyst (\( \text{H}_3\text{O}^+ \)) - Ethanol (\( \text{EtOH} \)) *Product:* - Cyclic hemiacetal with an ether and an ethyl group. **19.55** ✔️ **Correct.** Formation of a hemiacetal follows a common pattern for mechanisms of acid-catalyzed reactions: Protonate, Attack, Deprotonate (P.A.D.). **The first three steps of the mechanism involve the formation of a hemiacetal.** - **The first step is** *protonation of the carbonyl oxygen atom.* - **The second step is** *nucleophilic attack.* - **The third step is** *deprotonation of a positively charged oxygen atom.*
**Part 5** **Feedback:** Incorrect. Which of the four mechanistic steps is happening? **Instruction:** Add two curved arrow(s) to draw step 5 of the mechanism: collapse of a charged tetrahedral intermediate. Modify the given drawing of the product as needed to show the intermediate that is formed in this step. Use the +/- tools to add/remove charges, and use the single bond tool to interconvert between double and single bonds. **Diagram:** The image below shows a chemical mechanism involving the conversion of two structures. The left structure features a cyclohexane ring bonded to an oxonium ion. An oxygen atom with a positive charge is double-bonded to the cyclohexane ring, and has two lone pairs of electrons. The right structure shows a collapsed intermediate with an oxygen atom doubly bonded to the cyclohexane ring and bonded to an OH group, also carrying a positive charge on the oxygen. [Edit Drawing Button] **Hint:** The next step is the loss of a leaving group.
Transcribed Image Text:**Part 5** **Feedback:** Incorrect. Which of the four mechanistic steps is happening? **Instruction:** Add two curved arrow(s) to draw step 5 of the mechanism: collapse of a charged tetrahedral intermediate. Modify the given drawing of the product as needed to show the intermediate that is formed in this step. Use the +/- tools to add/remove charges, and use the single bond tool to interconvert between double and single bonds. **Diagram:** The image below shows a chemical mechanism involving the conversion of two structures. The left structure features a cyclohexane ring bonded to an oxonium ion. An oxygen atom with a positive charge is double-bonded to the cyclohexane ring, and has two lone pairs of electrons. The right structure shows a collapsed intermediate with an oxygen atom doubly bonded to the cyclohexane ring and bonded to an OH group, also carrying a positive charge on the oxygen. [Edit Drawing Button] **Hint:** The next step is the loss of a leaving group.
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