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

31. Catalysis in Organic Reactions

Nucleophilic Catalysis

Organic Chemistry

31. Catalysis in Organic Reactions

Nucleophilic Catalysis

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Multiple Choice

Which of the following compounds would you expect to have the greatest relative rate of reaction?

Chlorobenzene with NaF and NaCN reagents for nucleophilic catalysis.

Bromobenzene with NaOH and NaCN reagents for nucleophilic catalysis.

Chlorobenzene with KI and NaCN reagents for nucleophilic catalysis.

Phenol with LiCl and NaCN reagents for nucleophilic catalysis.

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Verified step by step guidance

Identify the type of reaction: The reactions shown are nucleophilic substitution reactions, where a nucleophile (NaCN) will replace a leaving group (Cl, Br, or OH) on the organic compound.

Evaluate the leaving group ability: In nucleophilic substitution reactions, the rate is often influenced by the leaving group. Generally, the order of leaving group ability is I > Br > Cl > OH. Therefore, compounds with better leaving groups will react faster.

Consider the solvent and conditions: The concentration and type of the first reagent (NaF, NaOH, KI, LiCl) can affect the reaction rate. Higher concentrations and more reactive reagents can increase the rate of reaction.

Analyze the structure of the substrate: The structure of the organic compound can also influence the reaction rate. For example, benzylic and allylic positions often react faster due to resonance stabilization of the transition state.

Compare the given options: Based on the leaving group ability, reagent concentration, and substrate structure, determine which compound is likely to have the greatest relative rate of reaction.