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

Nucleophilic Addition

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Nucleophilic Addition

Previous problemNext problem

3:39 minutes

Problem 67c

Textbook Question

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.
(c)

Verified step by step guidance

Analyze the structures provided: All three molecules are ketones, with varying substituents attached to the carbonyl carbon. The substituents are either fluorinated groups (CF3 or F3C) or methyl groups (CH3).

Understand the concept: Nucleophilic addition to a carbonyl group in basic conditions depends on the electrophilicity of the carbonyl carbon. Electrophilicity is influenced by the electron-withdrawing or electron-donating nature of the substituents attached to the carbonyl carbon.

Evaluate the substituents: Fluorine atoms are highly electronegative and act as strong electron-withdrawing groups. Substituents like CF3 or F3C increase the electrophilicity of the carbonyl carbon, making it more reactive toward nucleophilic attack. Methyl groups (CH3), on the other hand, are electron-donating and reduce the electrophilicity of the carbonyl carbon.

Rank the reactivity: The molecule with two CF3 groups (F3C-C=O-CF3) will react fastest because it has the most electron-withdrawing substituents, making the carbonyl carbon highly electrophilic. The molecule with one CF3 group and one CH3 group (H3C-C=O-CF3) will react slower than the first but faster than the molecule with two CH3 groups (H3C-C=O-CH3), which will react slowest due to the electron-donating nature of the methyl groups.

Conclude: The reactivity order toward nucleophilic addition in basic conditions is: F3C-C=O-CF3 (fastest) > H3C-C=O-CF3 > H3C-C=O-CH3 (slowest).

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 in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically in carbonyl compounds. This reaction is crucial for forming new carbon-carbon or carbon-heteroatom bonds. The rate of nucleophilic addition can be influenced by the electrophilicity of the carbonyl carbon and the strength of the nucleophile.

Electrophilicity

Electrophilicity refers to the tendency of a chemical species to accept electrons, making it a target for nucleophiles. In the context of carbonyl compounds, the carbon atom is electrophilic due to the partial positive charge created by the polarization of the carbon-oxygen double bond. Factors such as steric hindrance and the presence of electron-withdrawing groups can enhance or diminish electrophilicity, affecting reaction rates.

Basic Conditions

Basic conditions in organic chemistry typically involve the presence of a base that can deprotonate acidic protons, thereby increasing the nucleophilicity of certain species. In nucleophilic addition reactions, basic conditions can facilitate the formation of stronger nucleophiles, such as alkoxides, which can enhance the reaction rate. Understanding how pH and the nature of the base influence the reaction environment is essential for predicting reaction outcomes.

Watch next

Master Nucleophilic Addition with a bite sized video explanation from Johnny

Start learning

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.(c)

Key Concepts

Nucleophilic Addition

Electrophilicity

Basic Conditions

Watch next

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.
(c)