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

14. Synthetic Techniques

Retrosynthesis

Organic Chemistry

14. Synthetic Techniques

Retrosynthesis

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4:28 minutes

Problem 34f

Textbook Question

What reagents should be used to carry out the following syntheses?

Verified step by step guidance

Identify the starting material and the desired product for each reaction. The starting material is an alkyne (RC≡CH), and the products include alkenes, alkyl halides, and carbonyl compounds.

For the conversion of RC≡CH to RCH₂CH₃, use hydrogenation. The reagent required is H₂ with a metal catalyst such as Pd/C or PtO₂.

To convert RC≡CH to RCH=CH₂, perform a partial hydrogenation. Use H₂ with a Lindlar catalyst to selectively reduce the alkyne to a cis-alkene.

For the transformation of RC≡CH to RCHBrCH₃, use hydrohalogenation. The reagent needed is HBr, which adds across the triple bond to form a bromoalkene.

To synthesize the carbonyl compounds from RC≡CH, use hydration reactions. For example, to form a ketone, use H₂O with H₂SO₄ and HgSO₄ as catalysts to add water across the triple bond, resulting in a ketone after tautomerization.

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Key Concepts

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

Alkyne Reactivity

Alkynes, characterized by a carbon-carbon triple bond, exhibit unique reactivity patterns. They can undergo various reactions such as hydrogenation, halogenation, and hydration. Understanding these reactions is crucial for predicting the products formed when specific reagents are applied to alkynes in synthetic pathways.

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving unsaturated compounds like alkenes and alkynes. This concept is essential for understanding how reagents such as bromine or water can add across the triple bond of alkynes, leading to the formation of new functional groups.

Functional Group Transformation

Functional group transformation refers to the process of converting one functional group into another through chemical reactions. In the context of the provided synthesis question, recognizing how to transform alkynes into alcohols or other derivatives using specific reagents is vital for successful synthesis planning and execution.

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Related Practice

Textbook Question

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

Textbook Question

Which of the reactions cannot be used for the synthesis of isobutyl alcohol?

Textbook Question

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.