1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
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 Acids3h 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

21. Aldehydes and Ketones: Nucleophilic Addition

Organometallics on Ketones

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Organometallics on Ketones

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3:54 minutes

Problem 16-7aBruice - 8th Edition

Textbook Question

a. How many stereoisomers are obtained from the reaction of 2-pentanone with ethylmagnesium bromide followed by the addition of dilute acid?

Verified step by step guidance

Identify the reaction type: The reaction of 2-pentanone with ethylmagnesium bromide is a Grignard reaction, which forms a tertiary alcohol.

Determine the new chiral center: The addition of the Grignard reagent to the carbonyl group of 2-pentanone creates a new chiral center at the carbon where the nucleophilic addition occurs.

Assess the stereochemistry: Since a new chiral center is formed, consider the possible configurations (R or S) at this center.

Calculate the number of stereoisomers: For a molecule with n chiral centers, the maximum number of stereoisomers is 2^n. Here, n = 1, so calculate 2^1.

Conclude the stereoisomer count: Based on the calculation, determine the number of stereoisomers formed in the reaction.

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Key Concepts

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

Stereoisomerism

Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This can lead to different physical and chemical properties. In organic chemistry, stereoisomers can be classified into enantiomers and diastereomers, which are crucial for understanding the diversity of compounds formed in reactions.

Grignard Reagents

Grignard reagents are organomagnesium compounds that are highly reactive and used to form carbon-carbon bonds. In this case, ethylmagnesium bromide reacts with 2-pentanone, leading to the formation of a tertiary alcohol after the addition of dilute acid. Understanding the reactivity and mechanism of Grignard reagents is essential for predicting the products of such reactions.

Chiral Centers

A chiral center, typically a carbon atom, is bonded to four different substituents, leading to non-superimposable mirror images known as enantiomers. The formation of a chiral center during the reaction of 2-pentanone with ethylmagnesium bromide results in the potential for multiple stereoisomers. Identifying chiral centers is key to determining the number of stereoisomers produced in a reaction.