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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5:34 minutes

Problem 49b

Textbook Question

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

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Analyze the target molecule and identify its functional groups, carbon skeleton, and any stereochemistry. This will help determine the synthetic strategy.

Determine the number of carbons in the target molecule and compare it to the starting materials (organic molecules with three carbons or fewer). If the target molecule has more than three carbons, consider carbon-carbon bond-forming reactions such as aldol condensation, Grignard reactions, or alkylation.

Identify the functional groups in the target molecule and plan the sequence of reactions needed to introduce them. For example, if the target molecule contains an alcohol, consider reactions like hydroboration-oxidation or reduction of a carbonyl group.

Work backward using retrosynthetic analysis to break the target molecule into simpler precursors. Ensure that each step in the synthesis is feasible and uses reagents compatible with the functional groups present.

Combine the steps into a forward synthesis, starting with the allowed starting materials (three-carbon or fewer organic molecules). Clearly outline the reagents and conditions for each step, ensuring that the transformations lead to the desired target molecule.

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Key Concepts

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

Alkanes and Their Reactions

Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, with single bonds between carbon atoms. Understanding their structure and reactivity is crucial for synthesizing larger molecules. Reactions such as combustion, substitution, and elimination are fundamental in organic synthesis, especially when starting from simple alkanes.

Functional Groups

Functional groups are specific groups of atoms within molecules that determine the chemical reactivity and properties of those molecules. Recognizing functional groups such as alcohols, aldehydes, and carboxylic acids is essential for predicting the outcomes of chemical reactions and for planning synthetic pathways from simple organic molecules.

Synthetic Pathways

Synthetic pathways refer to the series of chemical reactions that transform starting materials into desired products. Understanding how to construct these pathways using available reagents and conditions is vital for synthesizing complex molecules from simpler precursors, particularly when limited to starting materials with three carbons or fewer.

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Related Practice

Textbook Question

How could the following compounds be synthesized from acetylene?

Textbook Question

Reaction of the acetylide with the epoxide shown will not form the desired product. What side reaction occurs instead? Why?

Textbook Question

Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While there can be multiple ways of doing each synthesis, the minimum number of steps necessary is indicated over each reaction arrow.

(b)

Textbook Question

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)

Textbook Question

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

(e)

Textbook Question

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

Textbook Question

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

Textbook Question

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

Key Concepts

Alkanes and Their Reactions

Functional Groups

Synthetic Pathways

Watch next

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