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

10. Addition Reactions

Acid-Catalyzed Hydration

Organic Chemistry

10. Addition Reactions

Acid-Catalyzed Hydration

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5:04 minutes

Problem 29

Textbook Question

Draw a mechanism for the acid-catalyzed conversion of DPP to IPP. How do you know that your mechanism is correct?

Verified step by step guidance

Identify the structures of DPP (Dimethylallyl pyrophosphate) and IPP (Isopentenyl pyrophosphate). Both are isomers and intermediates in the mevalonate pathway. DPP has a double bond at the terminal position, while IPP has a double bond in the internal position.

Recognize that the reaction is acid-catalyzed. This means a proton (H⁺) will be added to initiate the reaction. The acid catalyst will protonate the terminal double bond of DPP, forming a carbocation intermediate.

Draw the carbocation intermediate. Protonation of the double bond in DPP will result in a more stable secondary carbocation due to hyperconjugation and inductive effects.

Show the rearrangement of the carbocation. A 1,2-hydride shift occurs, where a hydrogen atom from the adjacent carbon migrates to stabilize the carbocation, forming a new carbocation at a different position.

Deprotonate the carbocation to regenerate the double bond in a new position, resulting in the formation of IPP. Verify the mechanism by ensuring that all steps follow the principles of stability (e.g., carbocation stability) and that the final product matches the structure of IPP.

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Key Concepts

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

Acid-Catalyzed Reactions

Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In organic chemistry, acids can donate protons (H+) to substrates, facilitating the formation of reactive intermediates. Understanding how acids interact with molecules is crucial for predicting the pathway and products of the reaction, such as the conversion of DPP to IPP.

Reaction Mechanism

A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. It outlines the sequence of bond-breaking and bond-forming events, including the formation of intermediates. Drawing a mechanism helps visualize the transformation of DPP to IPP, allowing chemists to understand the roles of various species and the overall energy changes involved.

Verification of Mechanisms

Verifying a reaction mechanism involves checking its consistency with experimental data and established chemical principles. This can include analyzing reaction rates, intermediates, and product distributions. A correct mechanism should align with known reactivity patterns and provide a plausible explanation for the observed outcomes, ensuring that the proposed steps are feasible under the given conditions.

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