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

Alkynide Alkylation

Organic Chemistry

14. Synthetic Techniques

Alkynide Alkylation

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7:04 minutes

Problem 106c

Textbook Question

Show how each of the following compounds can be synthesized from the given starting materials:
c.

Verified step by step guidance

Step 1: Identify the starting material and the target compound. The starting material is 2-chloropropane, and the target compound is 2-methylbutanal. The transformation involves extending the carbon chain and introducing an aldehyde functional group.

Step 2: Perform a nucleophilic substitution reaction to replace the chlorine atom in 2-chloropropane with a cyanide group (-CN). This can be achieved using sodium cyanide (NaCN) in an aprotic solvent like DMSO. The product will be 2-methylpropanenitrile.

Step 3: Hydrolyze the nitrile group (-CN) in 2-methylpropanenitrile to form a carboxylic acid. This can be done using acidic or basic hydrolysis. For example, refluxing with aqueous HCl or NaOH will yield 2-methylpropanoic acid.

Step 4: Convert the carboxylic acid group in 2-methylpropanoic acid to an aldehyde group. This can be achieved using a reduction reaction, such as the Rosenmund reduction, which involves hydrogenation of the acid chloride (prepared from the carboxylic acid) using Pd/BaSO4 catalyst.

Step 5: Verify the structure of the final product, 2-methylbutanal, ensuring that the carbon chain has been extended and the aldehyde functional group is correctly positioned.

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Key Concepts

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

Alkynes and Alkynide Ions

Alkynes are hydrocarbons containing at least one carbon-carbon triple bond. Alkynide ions are the conjugate bases of terminal alkynes, formed by deprotonation of the terminal hydrogen. These ions are strong nucleophiles and can participate in nucleophilic substitution reactions, allowing for the formation of new carbon-carbon bonds.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule with a nucleophile. In the context of alkynide alkylation, the alkynide ion acts as the nucleophile, attacking an alkyl halide to form a new carbon-carbon bond. This reaction is fundamental in organic synthesis for building complex molecules.

Synthesis of Aldehydes

Aldehydes are organic compounds characterized by the presence of a carbonyl group (C=O) at the end of a carbon chain. They can be synthesized from alkynes through various methods, including hydroboration-oxidation or ozonolysis. Understanding the reactivity of alkynes and the conditions required for these transformations is crucial for effective synthesis.

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Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal number of steps is indicated over the reaction arrow, although there may be alternate routes worth considering.

(b)

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Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(b)

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Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(e)

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For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

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Show how each of the following compounds can be prepared using the given starting material, any needed inorganic reagents, and any organic compound that has no more than four carbons:

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Show how each of the following compounds can be prepared using the given starting material, any needed inorganic reagents, and any organic compound that has no more than four carbons:

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Show how the following compound can be prepared from the given starting material. Draw the structure of the compound that is formed in each step of the synthesis.

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Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents

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