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

Previous problemNext problem

2:30 minutes

Problem 29f

Textbook Question

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.
(f)

Verified step by step guidance

Step 1: Identify the functional group transformation. The starting material contains a bromine atom attached to a carbon chain, and the product contains a terminal alkyne (-C≡CH). This suggests that the bromine atom will be replaced by an alkyne group through an elimination reaction followed by alkyne formation.

Step 2: Perform an elimination reaction to remove the bromine atom and form an alkene. Use a strong base such as potassium tert-butoxide (KOtBu) or sodium amide (NaNH2) to deprotonate the β-hydrogen and eliminate HBr, forming a double bond (alkene).

Step 3: Convert the alkene to a terminal alkyne. Treat the alkene with a strong base like sodium amide (NaNH2) in liquid ammonia (NH3) to generate the acetylide ion, followed by protonation with water or an acid to form the terminal alkyne.

Step 4: Ensure the carbonyl group (C=O) remains intact during the reaction. The reagents used for elimination and alkyne formation should not interfere with the ketone functional group.

Step 5: Verify the structure of the product. The final product should have the terminal alkyne (-C≡CH) attached to the carbon chain, with the ketone group (C=O) preserved at the original position.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Organic Synthesis

Organic synthesis is the process of constructing organic compounds through chemical reactions. It involves the strategic selection of starting materials and reagents to achieve desired products. Understanding the principles of synthesis is crucial for designing pathways that efficiently convert reactants into target molecules while considering factors like yield and selectivity.

Reagents and Reaction Mechanisms

Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. Each reagent can influence the reaction mechanism, which describes the step-by-step process of how reactants are converted into products. Familiarity with common reagents and their mechanisms is essential for predicting the outcomes of synthetic routes.

Functional Groups

Functional groups are specific groups of atoms within molecules that determine the chemical properties and reactivity of those molecules. Recognizing functional groups is vital in organic chemistry, as they guide the selection of appropriate reactions and reagents for synthesis. Understanding how different functional groups interact can help in predicting the behavior of compounds during chemical transformations.

Watch next

Master Sodium Alkynide Alkylation with a bite sized video explanation from Johnny

Start learning