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

Previous problemNext problem

2:50 minutes

Problem 54g

Textbook Question

What are the products of the following reactions?
g.

Verified step by step guidance

Step 1: Identify the functional groups in the starting material. The molecule shown is cyclopentenone, which contains both a ketone group (C=O) and a conjugated double bond in a five-membered ring.

Step 2: Recognize the reagents involved. Sodium cyanide (NaCN) is a source of cyanide ion (CN⁻), and hydrochloric acid (HCl) provides acidic conditions. This combination suggests a cyanohydrin formation reaction.

Step 3: Understand the mechanism. The cyanide ion (CN⁻) acts as a nucleophile and attacks the electrophilic carbon of the ketone group, forming a tetrahedral intermediate. The acidic conditions (HCl) then protonate the oxygen atom, stabilizing the product.

Step 4: Predict the product. The reaction results in the formation of a cyanohydrin, where the ketone group is converted into a hydroxyl group (-OH) and a cyano group (-CN) is added to the same carbon.

Step 5: Consider stereochemistry. If the reaction generates a chiral center, the product may exist as a racemic mixture (equal amounts of enantiomers) due to the non-stereoselective nature of the reaction.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically found in carbonyl compounds. In this case, the cyanide ion (CN-) from sodium cyanide (NaCN) acts as the nucleophile, attacking the carbonyl carbon of cyclopentanone, leading to the formation of a cyanohydrin.

Carbonyl Compounds

Carbonyl compounds, characterized by the presence of a carbon-oxygen double bond (C=O), include aldehydes and ketones. Cyclopentanone is a cyclic ketone, and its reactivity is influenced by the electrophilic nature of the carbonyl carbon, making it susceptible to nucleophilic attack, which is crucial for understanding the reaction with NaCN.

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In this reaction, HCl serves as an acid that can protonate the resulting cyanohydrin, stabilizing the product and influencing the reaction pathway. Understanding the role of acids in organic reactions is essential for predicting the final products and their stability.

Watch next

Master 1,2 vs 1,4 Addition with a bite sized video explanation from Johnny

Start learning