**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.

Given is a reaction of conversion of 5-hydroxypentanal to 2-ethoxytetrahydro-2H-pyran.

Answered: Propose a plausible mechanism for the…

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

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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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

**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.

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