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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3:55 minutes

Problem 20a

Textbook Question

Suggest reagents you might use to generate the product from the given reactant.
(a)

Verified step by step guidance

Step 1: Analyze the given reactant and product to identify the type of transformation required (e.g., addition, elimination, substitution, oxidation, reduction, etc.). This will help narrow down the possible reagents.

Step 2: Determine the functional groups present in the reactant and product. Compare them to see if any new functional groups are introduced or if existing ones are modified.

Step 3: Consider the stereochemistry of the product (if applicable). If the product has specific stereochemical requirements, select reagents that can achieve the desired stereochemical outcome.

Step 4: Match the transformation to common organic reactions. For example, if the product involves the addition of a hydroxyl group, you might consider hydration reactions or oxidation of an alcohol precursor.

Step 5: Select appropriate reagents based on the reaction type. For example, if the transformation involves oxidation, reagents like PCC (Pyridinium Chlorochromate) or KMnO₄ might be suitable. If reduction is required, reagents like NaBH₄ or LiAlH₄ could be used.

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Key Concepts

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

Reagents in Organic Chemistry

Reagents are substances that are added to a chemical reaction to cause a transformation. In organic chemistry, they can include acids, bases, oxidizing agents, reducing agents, and catalysts. Understanding the role of specific reagents is crucial for predicting the outcome of reactions and generating desired products from reactants.

Reaction Mechanisms

A reaction mechanism describes the step-by-step process by which reactants are converted into products. It includes the breaking and forming of bonds, the movement of electrons, and the intermediates formed during the reaction. Familiarity with mechanisms helps in selecting appropriate reagents and understanding how they influence the reaction pathway.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying the functional groups in both the reactant and the desired product is essential for determining which reagents will facilitate the necessary transformations to achieve the target compound.

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Related Practice

Textbook Question

Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]

(c)

Textbook Question

Ethinylestradiol is a synthetic hormone mimic used as a contraceptive for its ability to prevent ovulation. Suggest a mechanism for the synthesis using sodium acetylide and estrone, followed by quenching with acid.

Textbook Question

Predict the product of the following acetylide alkylations.

(a)

Textbook Question

Predict the product of the following acetylide alkylations.

(c)

Textbook Question

Suggest reagents you might use to generate the product from the given reactant.

(c)

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)

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.

(a)

Textbook Question

In Chapter 10, you learned how to make an alkyne by acetylide alkylation with a 1° haloalkane. Suggest a mechanism by which this reaction occurs.

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