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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2:52 minutes

Problem 36n

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(n)

Verified step by step guidance

Step 1: Analyze the reaction conditions. The reagent KMnO₄ under cold, dilute conditions is used for the oxidation of alkenes to form diols (glycols) via syn-dihydroxylation. This reaction adds hydroxyl (-OH) groups to the double bond in a syn fashion.

Step 2: Identify the structure of the starting material. The molecule contains a double bond (C=C) in the structure, which is the reactive site for KMnO₄ under these conditions.

Step 3: Predict the product formation. The double bond will undergo syn-dihydroxylation, meaning two hydroxyl groups (-OH) will be added to the carbons involved in the double bond. The stereochemistry of the addition will be syn, meaning both hydroxyl groups will be added to the same face of the molecule.

Step 4: Draw the product structure. For the given alkene, add -OH groups to the two carbons of the double bond. Ensure the stereochemistry reflects syn addition (both -OH groups on the same side of the molecule).

Step 5: Verify the product. Confirm that the resulting molecule is a vicinal diol (two hydroxyl groups on adjacent carbons) and that no other functional groups or parts of the molecule are altered under these reaction conditions.

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Key Concepts

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

Alkene Hydroxylation

Alkene hydroxylation is a chemical reaction where alkenes react with oxidizing agents, such as cold, dilute KMnO4, to form glycols. This reaction typically adds hydroxyl (-OH) groups across the double bond of the alkene, resulting in the formation of vicinal diols. Understanding this process is crucial for predicting the products of the given reaction.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the case of alkene hydroxylation, the regioselectivity is influenced by the stability of the carbocation intermediates and steric factors, which can affect the distribution of products formed during the reaction.

Stereochemistry of Products

Stereochemistry involves the spatial arrangement of atoms in molecules and how this affects their chemical properties. In the context of alkene reactions, the formation of diols can lead to different stereoisomers, such as cis and trans forms. Recognizing the stereochemical outcomes is essential for accurately depicting the products after hydrolysis.

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Related Practice

Textbook Question

Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.

(b)

Textbook Question

When using a terminal alkene under the conditions shown here, explain why it is unnecessary to show the relative stereochemical outcome in the product.

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?

(d)

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.

(e)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iv) 1. OsO₄ 2. NaHSO₃. If there is no reaction, write 'no reaction.'

(a)

Textbook Question

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(b)

Textbook Question

Predict the product of each of the following alcohol synthesis reactions.

(d)

Textbook Question

We have studied a number of pericyclic reactions previously. Draw the mechanism of the steps shown. The section number where this material was first studied is given for your review.

(d)

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Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).(n)

Key Concepts

Alkene Hydroxylation

Regioselectivity

Stereochemistry of Products

Watch next

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(n)