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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3:12 minutes

Problem 37f

Textbook Question

Predict the major products of the following reactions.
f. 1-ethylcycloheptene + cold, dilute KMnO₄

Verified step by step guidance

Identify the type of reaction: Cold, dilute KMnO4 is a reagent used for syn-dihydroxylation of alkenes. This reaction adds two hydroxyl (-OH) groups across the double bond in a syn (same side) fashion.

Locate the double bond in the given molecule: 1-ethylcycloheptene contains a double bond in the cycloheptene ring. The double bond is the site of the reaction.

Determine the stereochemistry of the addition: Since cold, dilute KMnO4 performs syn addition, the two hydroxyl groups will be added to the same face of the double bond.

Draw the intermediate structure: Break the π-bond of the double bond and add one hydroxyl group to each of the two carbons that were part of the double bond. Ensure that both hydroxyl groups are on the same side of the ring.

Verify the product: Confirm that the product is a 1,2-diol (vicinal diol) with the hydroxyl groups added in a syn fashion. The ethyl group on the cycloheptene ring remains unchanged.

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Key Concepts

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

Electrophilic Addition Reactions

Electrophilic addition reactions involve the addition of electrophiles to alkenes, where the double bond acts as a nucleophile. In the case of 1-ethylcycloheptene, the double bond can react with cold, dilute KMnO4, which serves as an electrophile, leading to the formation of a diol through syn-dihydroxylation.

Oxidation Reactions

Oxidation reactions in organic chemistry refer to the process where a molecule loses electrons, often involving the addition of oxygen or the removal of hydrogen. KMnO4 is a strong oxidizing agent, and in cold, dilute conditions, it selectively oxidizes alkenes to form vicinal diols, which are compounds with hydroxyl groups on adjacent carbon atoms.

Regioselectivity and Stereochemistry

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereochemistry deals with the spatial arrangement of atoms in molecules. In the reaction of 1-ethylcycloheptene with KMnO4, the regioselectivity will determine which carbon atoms are oxidized, and the stereochemistry will dictate whether the resulting diol is formed in a syn or anti manner.

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Related Practice

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

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.

(e)

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

a. fumaric acid to (±)-tartaric acid.

b. fumaric acid to meso-tartaric acid.

Textbook Question

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

c. 1-(hydroxymethyl)cyclohexanol

Textbook Question

What stereoisomers are obtained from the reaction of each of the following alkenes with OsO₄ followed by aqueous H₂O₂?

a. trans-2-butene

b. cis-2-butene

Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(f)

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Predict the major products of the following reactions.f. 1-ethylcycloheptene + cold, dilute KMnO4

Key Concepts

Electrophilic Addition Reactions

Oxidation Reactions

Regioselectivity and Stereochemistry

Watch next

Predict the major products of the following reactions.
f. 1-ethylcycloheptene + cold, dilute KMnO₄