Suggest a mechanism by which TXB 2 might be formed from TXA 2 in an acid-catalyzed hydrolysis reaction. [ The structure has been simplified. ]

Welcome back, everyone try the mechanism for the acid catalyzed hydrolysis reaction given below. We're given our starting material. And what we notice is that we are opening one of our ranks, right, which is above the six member rank. So what we have to notice is that if we're using a strong acid, the first step in our mechanism will be the protonation step because we have two oxygens and we are going to take the oxygen that is above the six member grain in our first step because it's experiencing a more significant strain. In addition to that, we notice that on the product side, the oxygen atom within the six member ring is not affected. So this is a huge hint for us. What we're going to do is just to draw the protonation step. So let's draw a hydro oxygen gets a formal positive charge. We need to add a, a lump pair on oxygen to indicate the protonation step. Let's show the proton capture and the release of water. So in the first step, we obtain the protein at intermediate, what we're going to do is just draw our oxygen hydrogen bond, it's sufficient to add hydrogen to oxygen and indicate that oxygen gets a formal positive charge. Now, in the next step, we're going to open that ring using water. Previously, we got water and now it can act as a Nile attacking one of the electro carbon atoms. The the one that we're going to attack will be the bottom one because there's an adjacent oxygen atom that is electron withdrawing and increasing the electro of the bottom carbon. So now water will attack the bottom carbon as a Nile followed by the ring opening, which is also consistent with the change in configuration. So let's see what we got here. Now that we are opening our ring, we're going to observe the top alcohol group pointing up on a wedge. Since there is no inversion of no inversion of configuration, this specific carbon is not attacked. So we're going to draw a simple wedge to indicate the retention in configuration, we immediately get the required alcohol group. And now on the bottom, since we have a backside attack, we're going to observe an inversion of configuration. That means we're adding a watch. However, oxygen has two hydrogens bonded to it. So oxygen now has a formal positive charge and we are simply going to use another molecule of water to deproteinate it. So let's draw water, let's add a long pair to oxygen. And let's indicate an acid base reaction or basically the dep protonation stuff in the step, we get the required product. So let's go ahead and throw it for simplicity, we can just add the previously drawn structure and slightly modify it since we're simply removing that hydrogen. And this allows us to get the required alcohol. In addition to that, we can indicate H 30 plus, right? Since water captures a proton, and this is where we can finish our mechanism because we have arrived at the final product. Thank you for watching.

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1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

12. Alcohols, Ethers, Epoxides and Thiols

Ether Cleavage

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Ether Cleavage

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Problem 65

Textbook Question

Suggest a mechanism by which TXB₂ might be formed from TXA₂ in an acid-catalyzed hydrolysis reaction. [The structure has been simplified.]

Verified step by step guidance

Identify the starting material TXA₂, which contains an epoxide functional group. This is characterized by a three-membered cyclic ether, which is highly strained and reactive.

Recognize that the reaction involves acid-catalyzed hydrolysis. The acid will protonate the epoxide oxygen, increasing the electrophilicity of the epoxide carbon atoms.

Once protonated, the epoxide ring is more susceptible to nucleophilic attack. Water, acting as a nucleophile, will attack one of the electrophilic carbon atoms of the epoxide, leading to ring opening.

The ring opening results in the formation of a diol, where two hydroxyl groups are added to the carbons that were originally part of the epoxide. This is evident in the product structure TXB₂.

The functional group formed in TXB₂ is a vicinal diol, characterized by two hydroxyl groups on adjacent carbon atoms. This transformation is typical of epoxide hydrolysis reactions.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acid-Catalyzed Hydrolysis

Acid-catalyzed hydrolysis is a chemical reaction where water is used to break down a compound in the presence of an acid. The acid donates protons (H⁺) to facilitate the reaction, often enhancing the electrophilicity of the substrate. This process is crucial in organic chemistry for converting esters, amides, and other functional groups into their corresponding acids or alcohols.

Mechanism of Reaction

The mechanism of a reaction describes the step-by-step sequence of elementary reactions by which overall chemical change occurs. Understanding the mechanism is essential for predicting the products and intermediates formed during the reaction. In the case of TXB₂ formation from TXA₂, identifying the key intermediates and transition states will clarify how the transformation occurs under acidic conditions.

Structural Changes in Organic Compounds

Structural changes in organic compounds refer to the alterations in the arrangement of atoms within a molecule during a chemical reaction. These changes can involve bond breaking and forming, leading to the creation of new functional groups or isomers. Recognizing how TXA₂ can be converted to TXB₂ involves understanding these structural transformations and the stability of intermediates formed during the reaction.

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