Table of contents

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

3. Acids and Bases

Reaction Mechanism

Organic Chemistry

3. Acids and Bases

Reaction Mechanism

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Problem 57b

Textbook Question

Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Two arrows are necessary in each reaction.
(b)

Verified step by step guidance

Step 1: Identify the reactants and products. The reactant is a protonated ketone (with a positively charged oxygen atom) and water (H₂O). The product is a hydrated form of the ketone, where water has added to the carbonyl group.

Step 2: Recognize the mechanism type. This is an acid-catalyzed hydration reaction, where water acts as a nucleophile and attacks the electrophilic carbonyl carbon.

Step 3: First arrow-pushing step: Draw an arrow from the lone pair of electrons on the oxygen atom of water (H₂O) to the carbonyl carbon of the protonated ketone. This represents the nucleophilic attack of water on the carbonyl carbon.

Step 4: Second arrow-pushing step: Draw an arrow from the double bond of the carbonyl group to the positively charged oxygen atom. This represents the breaking of the π bond and the formation of a single bond between the carbon and oxygen.

Step 5: Final structure: The product is formed with the addition of water to the carbonyl group, resulting in a hydrated structure where the oxygen atom of water is now bonded to the carbonyl carbon, and the original oxygen atom retains its positive charge.

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Key Concepts

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

Arrow-Pushing Mechanism

Arrow-pushing mechanisms are diagrams used in organic chemistry to illustrate the movement of electrons during chemical reactions. The arrows indicate the direction of electron flow, showing how bonds are formed or broken. Understanding this mechanism is crucial for predicting the products of reactions and visualizing the transition states.

Nucleophiles and Electrophiles

Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept an electron pair. Recognizing the roles of nucleophiles and electrophiles in a reaction is essential for determining how reactants interact and what products are formed. This concept is fundamental in understanding reaction mechanisms.

Reaction Intermediates

Reaction intermediates are transient species that form during the conversion of reactants to products. They are often unstable and exist only for a short time. Identifying these intermediates can provide insight into the steps of a reaction mechanism and help predict the final products, making them a key aspect of understanding complex organic reactions.

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