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

Dihydroxylation

Organic Chemistry

10. Addition Reactions

Dihydroxylation

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1:45 minutes

Problem 51f

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(f)

Verified step by step guidance

Step 1: Begin with methylenecyclohexane as the starting material. This compound contains a double bond, which can be used for functional group transformations.

Step 2: Perform a dihydroxylation reaction to add two hydroxyl groups (-OH) across the double bond. Use a reagent such as osmium tetroxide (OsO₄) in the presence of a co-oxidant like N-methylmorpholine N-oxide (NMO) or potassium permanganate (KMnO₄) under mild conditions.

Step 3: Ensure the reaction proceeds with syn addition, meaning both hydroxyl groups will add to the same side of the double bond, resulting in a cis-1,2-diol.

Step 4: After the reaction, isolate and purify the product using techniques such as extraction and recrystallization to obtain the desired compound.

Step 5: Confirm the structure of the synthesized compound using spectroscopic methods such as NMR (nuclear magnetic resonance) and IR (infrared spectroscopy) to verify the presence of the hydroxyl groups and the diol structure.

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Key Concepts

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

Synthesis in Organic Chemistry

Synthesis in organic chemistry refers to the process of constructing complex organic compounds from simpler ones. This involves a series of chemical reactions that transform starting materials into desired products, often requiring knowledge of reaction mechanisms, functional group transformations, and the use of reagents. Understanding synthesis is crucial for designing pathways to create specific compounds, such as those derived from methylenecyclohexane.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the question, the presence of hydroxyl (OH) groups in the target compounds indicates that the synthesis will involve reactions that introduce or modify these functional groups. Recognizing and manipulating functional groups is essential for predicting the behavior of organic compounds during synthesis.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step sequence of elementary reactions by which overall chemical change occurs. Understanding these mechanisms is vital for predicting the products of reactions involving methylenecyclohexane, as it allows chemists to anticipate how different reagents will interact with the starting material. Knowledge of mechanisms also aids in optimizing conditions for desired outcomes in synthetic pathways.

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Related Practice

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃

(f)

Textbook Question

Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?

(c)

Textbook Question

How might you make the catalytic cycle in Figure 9.31 more sustainable while still using NMO as the co-oxidant?

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Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(d)

Textbook Question

Predict the major products of the following reactions, including stereochemistry.

e. trans-pent-2-ene + OsO₄/H₂O₂

Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

d. a mixture of osmic acid and hydrogen peroxide

Textbook Question

The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how you would convert

b. fumaric acid to meso-tartaric acid.

Textbook Question

(e)

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