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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3:53 minutes

Problem 106b

Textbook Question

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

Verified step by step guidance

Identify the functional groups present in the target compound and the starting material. This will help in determining the type of reactions needed to transform the starting material into the target compound.

Determine the carbon skeleton of the target compound and compare it with the starting material. Check if there is a need for carbon-carbon bond formation or cleavage.

Consider the reagents and conditions required for each transformation. For example, if the target compound has an alcohol group and the starting material is an alkene, an oxymercuration-demercuration reaction might be appropriate.

Plan the synthesis by outlining a sequence of reactions that will convert the starting material into the target compound. This may involve multiple steps, such as functional group interconversion, protection/deprotection of functional groups, or rearrangement reactions.

Verify the proposed synthetic route by ensuring that each step is feasible under the given conditions and that the overall transformation is efficient and practical.

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Key Concepts

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

Synthetic Pathways

Synthetic pathways refer to the series of chemical reactions and transformations that convert starting materials into desired products. Understanding these pathways is crucial for designing a synthesis, as it involves selecting appropriate reagents, reaction conditions, and mechanisms to achieve the target compound efficiently.

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 in both starting materials and target compounds is essential for predicting reactivity and determining the necessary transformations during synthesis.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step sequence of elementary reactions that occur during a chemical transformation. A solid grasp of mechanisms helps chemists understand how and why reactions occur, allowing for the prediction of products and the optimization of synthetic routes.

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Related Practice

Textbook Question

Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.

(d)

Textbook Question

Show how the following compounds can be prepared, using ethyne as one of the starting materials:

2. 1-phenyl-2-butyn-1-ol

Textbook Question

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

g. pentanal, CH₃CH₂CH₂CH₂CHO

h. pentan-2-one, CH₃–CO–CH₂CH₂CH₃

i. (±) 3,4-dibromohexane

Textbook Question

How can the following compounds be prepared using ethyne as the starting material?

Textbook Question

Suggest a method for synthesizing the following alkynes using an alkyne and an alkyl halide. [There are two correct answers for each product.]

(c)

Textbook Question

When doing synthesis, you will often find yourself repeating the same series of steps. To see this in action, synthesize the following aldehydes beginning with an organic molecule containing three carbons or fewer.

(d)

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:

Textbook Question

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

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

Key Concepts

Synthetic Pathways

Functional Groups

Reaction Mechanisms

Watch next

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