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

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enolate Alkylation and Acylation

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enolate Alkylation and Acylation

Previous problemNext problem

1:51 minutes

Problem 72c

Textbook Question

Draw the products of the following reactions:
c.

Verified step by step guidance

Analyze the structure of the reactant: The molecule contains two ketone groups and a chlorine atom attached to a stereogenic center. The reaction involves hydroxide ion (HO⁻), which is a strong nucleophile and base.

Identify the reactive sites: The chlorine atom is a good leaving group, and the hydroxide ion can act as a nucleophile to replace the chlorine via an SN2 mechanism. Additionally, the hydroxide ion can deprotonate acidic hydrogens if present.

Predict the mechanism: The hydroxide ion will attack the carbon bonded to the chlorine atom, displacing the chlorine in an SN2 reaction. This will invert the stereochemistry at the carbon center due to the backside attack characteristic of SN2 reactions.

Consider the stability of the product: The resulting molecule will have a hydroxyl group (-OH) replacing the chlorine atom. The stereochemistry of the hydroxyl group will be inverted compared to the original chlorine atom.

Draw the product: Replace the chlorine atom with a hydroxyl group (-OH) at the stereogenic center, ensuring the stereochemistry is inverted. The rest of the molecule, including the ketone groups, remains unchanged.

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.

Enolate Formation

Enolates are formed from carbonyl compounds (like ketones or aldehydes) through deprotonation at the alpha carbon. This process generates a resonance-stabilized anion that can act as a nucleophile in subsequent reactions. Understanding enolate formation is crucial for predicting the products of reactions involving carbonyl compounds.

Alkylation of Enolates

Alkylation of enolates involves the nucleophilic attack of the enolate on an alkyl halide, leading to the formation of a new carbon-carbon bond. This reaction is significant in organic synthesis as it allows for the introduction of alkyl groups to carbonyl compounds, expanding the complexity of the molecule. The choice of alkyl halide can influence the regioselectivity and stereochemistry of the product.

Reactivity of Carbonyl Compounds

Carbonyl compounds, such as aldehydes and ketones, exhibit unique reactivity due to the polarized carbon-oxygen double bond. This polarization makes the carbon atom electrophilic, allowing it to participate in various nucleophilic addition reactions. Understanding the reactivity of carbonyls is essential for predicting the outcomes of reactions involving these functional groups, including their interactions with enolates.

Watch next

Master General Reaction with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

How could each of the following compounds be prepared from cyclohexanone?

Textbook Question

How could each of the following compounds be prepared from cyclohexanone?

Textbook Question

Draw the products of the following reactions:

c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl

Textbook Question

How could you prepare the following compound using a starting material that contains no more than three carbons?

Textbook Question

Show how 4-methyl-3-hexanol can be synthesized from 3-pentanone.

Textbook Question

Show how you would accomplish the following multistep conversions. You may use any additional reagents you need.

(a)

Multiple Choice

Determine if the reaction is thermodynamically or kinetically controlled

Textbook Question

The following are all substitution reactions, two of which we study in later chapters. With no knowledge of mechanism, what would you expect the ratio of products to be for each reaction, based on a random statistical distribution?

(a) Replacing a hydrogen (H) with deuterium (D):

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap