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

3. Acids and Bases

Reaction Mechanism

Organic Chemistry

3. Acids and Bases

Reaction Mechanism

Previous problemNext problem

Problem 62c

Textbook Question

The product of the Stille coupling reaction (A) tautomerizes in a basic solution to give compound B. B spontaneously converts to C.
(c) Suggest a mechanism for the conversion of B to C

Verified step by step guidance

Identify the structure of compound B and compound C. Understanding the functional groups and connectivity in these compounds is crucial for proposing a mechanism.

Consider the possible tautomerization or rearrangement processes that could occur in compound B. Look for functional groups that can undergo such transformations, such as enol-keto tautomerism or migration of double bonds.

Propose a mechanism for the conversion of B to C. This typically involves identifying a nucleophilic site in B that can attack an electrophilic site, leading to a rearrangement or formation of new bonds.

Draw the step-by-step mechanism, showing the movement of electrons using curved arrows. Ensure that each step is chemically feasible and follows the principles of organic chemistry, such as conservation of charge and atom connectivity.

Verify the proposed mechanism by checking if the final structure matches compound C. Ensure that all atoms and charges are accounted for and that the mechanism is consistent with known chemical behavior.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

Key Concepts

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

Stille Coupling Reaction

The Stille coupling reaction is a palladium-catalyzed cross-coupling process that forms carbon-carbon bonds between organotin compounds and organic halides. It is widely used in organic synthesis to construct complex molecules. Understanding the mechanism of this reaction is crucial for predicting the structure of the initial product (A) before it undergoes further transformations.

Tautomerization

Tautomerization is a chemical reaction that results in the rearrangement of bonds within a molecule, typically involving the transfer of a hydrogen atom and a switch of a single bond and adjacent double bond. In a basic solution, this process can lead to the conversion of one isomer into another, such as keto-enol tautomerism, which is essential for understanding how compound A transforms into compound B.

Mechanism of Spontaneous Conversion

The spontaneous conversion of compound B to C involves understanding the reaction mechanism, which includes identifying the intermediates and transition states. This process often involves rearrangements, eliminations, or additions that occur without external reagents. Analyzing the stability and reactivity of B can provide insights into the driving forces and steps leading to the formation of C.

Watch next

Master How to tell if a molecule will be reactive or not. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.

Textbook Question

Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.

Textbook Question

Propose a mechanism for the rearrangement that converts an ⍺-hydroxyimine to an ⍺-aminoketone in the presence of a trace amount of acid.

Textbook Question

Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.

Textbook Question

Aluminum trichloride (AlCl₃) dissolves in ether with the evolution of a large amount of heat. (In fact, this reaction can become rather violent if it gets too warm.) Show the structure of the resulting aluminum chloride etherate complex.

Multiple Choice

Which of the following analogies best describes the induced-fit model of enzyme-substrate binding?

Multiple Choice

Which graph best represents the energy profile of a reaction when an enzyme is present?

Multiple Choice

In the context of reaction mechanisms, what do both the rho-dependent and rho-independent mechanisms of termination have in common?

Show more practices