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

13. Alcohols and Carbonyl Compounds

Grignard Reaction

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Grignard Reaction

Previous problemNext problem

3:18 minutes

Problem 44a

Textbook Question

A chemist failed to generate the alcohol using the reaction shown here.
(a) Suggest a reason why this reaction did not work as written.

Verified step by step guidance

Step 1: Analyze the reaction provided. Determine the type of reaction (e.g., reduction, substitution, addition) and identify the reagents and conditions used. This will help you understand the intended transformation and why the alcohol product was expected.

Step 2: Consider the mechanism of the reaction. For example, if the reaction involves reduction, check if the reducing agent is appropriate for the substrate. If the substrate is resistant to reduction under the given conditions, this could explain the failure.

Step 3: Evaluate the functional groups present in the substrate. Some functional groups may require specific conditions or catalysts to undergo transformation. For instance, if the substrate contains a carbonyl group, the choice of reducing agent and solvent can significantly impact the reaction outcome.

Step 4: Suggest a reason for the failure. Common issues include insufficient reactivity of the reagents, inappropriate solvent, or lack of a necessary catalyst. For example, if the reaction involves a carbonyl compound, the reducing agent might not be strong enough to reduce it to an alcohol.

Step 5: Propose general modifications to the reaction conditions. This could include using a stronger reducing agent (e.g., LiAlH₄ instead of NaBH₄), changing the solvent to one that better stabilizes intermediates, or adding a catalyst to facilitate the reaction. These adjustments can improve the likelihood of forming the desired alcohol product.

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.

Reaction Mechanism

A reaction mechanism outlines the step-by-step process by which reactants are converted into products. Understanding the mechanism is crucial for identifying potential issues in a reaction, such as the formation of intermediates or the need for specific catalysts. In this case, knowing the mechanism can help explain why the alcohol was not produced as expected.

Reaction Conditions

Reaction conditions refer to the specific parameters under which a chemical reaction occurs, including temperature, pressure, solvent, and concentration of reactants. Modifying these conditions can significantly influence the reaction's outcome, potentially enhancing the yield of the desired product. Adjusting factors like temperature or using a different solvent may facilitate the formation of the alcohol.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing the functional groups involved in the reaction is essential for predicting reactivity and understanding how to modify conditions to promote product formation. In this scenario, the nature of the functional groups in the reactants and products will guide the chemist in troubleshooting the reaction.

Watch next

Master Reactions of Organometallics with a bite sized video explanation from Johnny

Start learning