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

25. Condensation Chemistry

Conjugate Addition

Organic Chemistry

25. Condensation Chemistry

Conjugate Addition

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2:35 minutes

Problem 51a

Textbook Question

What is the major product of each of the following reactions?
a.

Verified step by step guidance

Step 1: Analyze the structure of the starting material. The molecule is a cyclic ketone (cyclohexanone derivative) with a methyl group at the 2-position and a double bond at the 3-position.

Step 2: Identify the reagents. Potassium cyanide (KCN) in water is used, which suggests a nucleophilic addition reaction involving cyanide ion (CN⁻). Cyanide is a strong nucleophile.

Step 3: Determine the site of reactivity. The carbonyl group (C=O) is highly electrophilic due to the partial positive charge on the carbon atom. The cyanide ion will attack this carbon atom, leading to the formation of a cyanohydrin.

Step 4: Predict the mechanism. The cyanide ion attacks the carbonyl carbon, breaking the π bond of the C=O group. This results in the formation of a tetrahedral intermediate, which is stabilized by protonation from water to form the cyanohydrin.

Step 5: Consider stereochemistry. Since the starting material is cyclic and the reaction creates a new chiral center, the product may exist as a mixture of stereoisomers (enantiomers) depending on the orientation of the cyanide addition.

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Key Concepts

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

Conjugate Addition

Conjugate addition refers to the nucleophilic addition of a reagent to an α,β-unsaturated carbonyl compound. In this reaction, the nucleophile attacks the β-carbon, leading to the formation of a new bond while the double bond shifts. This process is crucial in organic synthesis as it allows for the formation of more complex molecules from simpler ones.

Nucleophiles

Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. In the context of the given reaction, KCN acts as a nucleophile, where the cyanide ion (CN-) attacks the electrophilic carbon of the carbonyl group. Understanding the nature of nucleophiles is essential for predicting the outcome of organic reactions.

Hydrolysis

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the context of the reaction shown, after the nucleophilic addition of KCN, hydrolysis occurs when water is used to convert the intermediate into a stable product, typically resulting in the formation of a hydroxyl group. This step is vital for completing the reaction and determining the final product.

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Related Practice

Textbook Question

Predict the product of the following reactions.

(c)

Textbook Question

a. Propose a mechanism for the following reaction:

Textbook Question

Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.

(a)

Textbook Question

Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.

(b)

Textbook Question

Propose a mechanism for the conjugate addition of a nucleophile (Nuc:^–) to acrylonitrile (H₂C=CHCN). Use resonance forms to show how the cyano activate the double bond toward conjugate addition.

Textbook Question

Propose a mechanism for the conjugate addition of a nucleophile (Nuc:^–) to acrylonitrile (H₂C=CHCN) and to nitroethylene. Use resonance forms to show how the cyano and nitro groups activate the double bond toward conjugate addition.

Multiple Choice

Predict the major, organic product for the following reaction.

Textbook Question

Propose a mechanism for each of the following reactions:

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