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

21. Aldehydes and Ketones: Nucleophilic Addition

Hydrates

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Hydrates

Next problem

3:40 minutes

Problem 13a

Textbook Question

Propose mechanisms for
(a) the acid-catalyzed hydration of chloral to form chloral hydrate.

Verified step by step guidance

Identify the reactants and products: The reactant is chloral (CCl₃CHO), and the product is chloral hydrate (CCl₃CH(OH)₂). This reaction involves the addition of water to the carbonyl group of chloral under acidic conditions.

Step 1: Protonation of the carbonyl group. The acid catalyst donates a proton (H⁺) to the oxygen atom of the carbonyl group in chloral, increasing the electrophilicity of the carbonyl carbon. This forms a protonated intermediate.

Step 2: Nucleophilic attack by water. A water molecule acts as a nucleophile and attacks the electrophilic carbonyl carbon, forming a tetrahedral intermediate. This step introduces an -OH group to the carbon.

Step 3: Deprotonation of the intermediate. The tetrahedral intermediate formed in the previous step undergoes deprotonation (loss of H⁺) to stabilize the structure, resulting in the formation of a geminal diol (chloral hydrate).

Step 4: Regeneration of the acid catalyst. The proton (H⁺) lost during the deprotonation step is returned to the solution, ensuring that the acid catalyst is regenerated and the reaction can proceed catalytically.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Acid-Catalyzed Hydration

Acid-catalyzed hydration is a chemical reaction where water is added to a compound in the presence of an acid, which acts as a catalyst. The acid protonates the carbonyl oxygen of the compound, increasing its electrophilicity and facilitating the nucleophilic attack by water. This process is crucial in converting carbonyl compounds into their corresponding alcohols or hydrates.

Chloral and Chloral Hydrate

Chloral is an organic compound with the formula CCl3CHO, characterized by its carbonyl group. When chloral undergoes hydration, it forms chloral hydrate, a stable compound used in various applications, including as a sedative. Understanding the structure and reactivity of chloral is essential for proposing the hydration mechanism.

Mechanism of Nucleophilic Addition

The mechanism of nucleophilic addition involves the attack of a nucleophile, such as water, on an electrophilic center, typically a carbon atom in a carbonyl group. This reaction proceeds through the formation of a tetrahedral intermediate, which can then collapse to yield the final product. Recognizing this mechanism is vital for understanding how chloral is converted to chloral hydrate.

Watch next

Master Mechanism with a bite sized video explanation from Johnny

Start learning