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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12:20 minutes

Problem 44

Textbook Question

Suggest a mechanism for the synthesis of farnesol beginning with IPP and DPP.

Verified step by step guidance

Step 1: Identify the starting materials. IPP (isopentenyl pyrophosphate) and DPP (dimethylallyl pyrophosphate) are both five-carbon isoprenoid units. Farnesol is a 15-carbon compound, so the synthesis involves combining three isoprenoid units.

Step 2: Perform the first coupling reaction. DPP acts as the electrophile, and IPP acts as the nucleophile. The pyrophosphate group of DPP is displaced, forming a 10-carbon intermediate called geranyl pyrophosphate (GPP). This reaction is catalyzed by geranyl pyrophosphate synthase.

Step 3: Perform the second coupling reaction. GPP now acts as the electrophile, and another molecule of IPP acts as the nucleophile. The pyrophosphate group of GPP is displaced, forming a 15-carbon intermediate called farnesyl pyrophosphate (FPP). This reaction is catalyzed by farnesyl pyrophosphate synthase.

Step 4: Hydrolyze the pyrophosphate group of FPP. The pyrophosphate group is removed, yielding farnesol. This step is typically catalyzed by a phosphatase enzyme.

Step 5: Verify the structure of farnesol. Farnesol contains three isoprenoid units, two double bonds in the trans configuration, and a terminal hydroxyl group. Ensure the stereochemistry and functional groups match the target molecule.

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Key Concepts

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

Isoprenoid Biosynthesis

Isoprenoid biosynthesis is a fundamental pathway in organic chemistry that involves the formation of isoprene units, which are the building blocks of many natural products. In this context, isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DPP) are key intermediates that undergo condensation reactions to form larger isoprenoid compounds, such as farnesol.

Condensation Reactions

Condensation reactions are chemical processes where two molecules combine to form a larger molecule, releasing a small molecule, often water. In the synthesis of farnesol, IPP and DPP undergo a series of condensation reactions, where they join together to create longer carbon chains, ultimately leading to the formation of farnesol through sequential addition of isoprene units.

Farnesol Structure and Function

Farnesol is a sesquiterpene alcohol with a specific structure that includes three isoprene units. Understanding its structure is crucial for predicting its reactivity and potential applications, such as in fragrance and flavor industries. The synthesis of farnesol from IPP and DPP highlights the importance of structural features in organic compounds and their biological significance.

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Related Practice

Textbook Question

Provide the expected product for the reaction of each of the following alkenes with H₂SO₄ and H₂O.

(d)

Textbook Question

A chemist unsuccessfully attempted to produce the 1,4-cyclohexanediol by hydration of the cyclohexene shown.

(a) Provide a mechanism for the formation of the actual product.

(b) Suggest a pathway using acetyl chloride as a protecting group that will allow for the formation of the desired product.

Textbook Question

The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.

(d) How might you shift the equilibrium to the right?

Textbook Question

When combining isoprene equivalents, IPP is never the electrophile. Why might this be? What is special about DPP that allows it to function better as an electrophile? [Draw the carbocation that each becomes.]

Open Question

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

Textbook Question

Provide the expected product for the reaction of each of the following alkenes with H₂SO₄ and H₂O.

(b)

Textbook Question

The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.

(b) Without looking back, how do you know this mechanism is correct?

Textbook Question

The pK_a values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98.

b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH 3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.

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