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

9. Alkenes and Alkynes

Acetylide

Organic Chemistry

9. Alkenes and Alkynes

Acetylide

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3:16 minutes

Problem 21b

Textbook Question

A student provided the product of the following reactions, but made a mistake. Identify the mistake, correct the mistake, and suggest a way for the student to avoid that mistake in the future.
(b)

Verified step by step guidance

Step 1: Carefully analyze the reaction provided by the student, including the reactants, reagents, and conditions. Identify the type of reaction (e.g., substitution, elimination, addition, etc.) and the expected mechanism (e.g., SN1, SN2, E1, E2).

Step 2: Compare the product provided by the student with the expected product based on the reaction mechanism. Look for discrepancies such as incorrect regiochemistry, stereochemistry, or functional group transformations.

Step 3: Identify the specific mistake made by the student. For example, if the reaction is an SN2 reaction, check if the student accounted for inversion of configuration at the stereocenter. If it is an E2 reaction, verify if the correct alkene (Zaitsev or Hofmann product) was formed.

Step 4: Correct the mistake by explaining the proper reaction mechanism and the correct product. Use clear reasoning to show why the expected product is different from the one provided by the student.

Step 5: Suggest a strategy for the student to avoid similar mistakes in the future. For example, recommend practicing reaction mechanisms, paying attention to stereochemistry, or using a reaction roadmap to predict products systematically.

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. A clear grasp of mechanisms helps in predicting the products of reactions and recognizing potential errors in proposed mechanisms.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups is essential for predicting reactivity and understanding how different compounds will behave in reactions. Mistakes often arise from misidentifying or overlooking these groups, leading to incorrect product predictions.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is particularly important in reactions that form chiral centers, as different stereoisomers can have vastly different properties. A common mistake is failing to account for stereochemical outcomes, which can lead to incorrect product structures.

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