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

9. Alkenes and Alkynes

Alkynide Synthesis

Organic Chemistry

9. Alkenes and Alkynes

Alkynide Synthesis

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6:02 minutes

Problem 28e

Textbook Question

How could the following compounds be synthesized from acetylene?
e.

Verified step by step guidance

Step 1: Begin with acetylene (C≡CH) as the starting material. Acetylene is a versatile precursor in organic synthesis due to its triple bond, which can undergo various reactions to form longer carbon chains.

Step 2: Perform a chain elongation reaction using alkylation. Treat acetylene with sodium amide (NaNH₂) to generate the acetylide ion (C≡C⁻). Then, react the acetylide ion with an alkyl halide, such as 1-bromopropane (CH₃CH₂CH₂Br), to form a longer alkyne chain (CH₃CH₂CH₂C≡CH).

Step 3: Hydrogenate the alkyne partially to form an alkene. Use a Lindlar catalyst to selectively reduce the triple bond to a cis-alkene (CH₃CH₂CH₂CH=CH₂). This step ensures the compound retains unsaturation for further functionalization.

Step 4: Perform hydroboration-oxidation to convert the alkene into an alcohol. React the alkene (CH₃CH₂CH₂CH=CH₂) with BH₃·THF followed by oxidation with hydrogen peroxide (H₂O₂) in a basic medium (NaOH). This yields a primary alcohol (CH₃CH₂CH₂CH₂CH₂OH).

Step 5: Oxidize the alcohol to a ketone. Use an oxidizing agent such as PCC (Pyridinium Chlorochromate) or Jones reagent (CrO₃/H₂SO₄) to convert the alcohol (CH₃CH₂CH₂CH₂CH₂OH) into the desired ketone (CH₃CH₂CH₂CH₂CO).

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Key Concepts

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

Acetylene Reactivity

Acetylene (C2H2) is a highly reactive alkyne that can undergo various reactions, including addition reactions with electrophiles. Understanding its reactivity is crucial for synthesizing more complex compounds. The triple bond in acetylene can be broken to form new bonds with other atoms or groups, allowing for the construction of diverse organic molecules.

Functional Group Transformations

Functional groups are specific groups of atoms within molecules that determine their chemical reactivity. In organic synthesis, transforming one functional group into another is a common strategy. Recognizing how to manipulate functional groups during the synthesis process is essential for creating the desired compounds from acetylene.

Synthetic Pathways

Synthetic pathways refer to the series of chemical reactions that lead to the formation of a target compound from starting materials. In the context of synthesizing compounds from acetylene, it is important to identify the appropriate sequence of reactions, including any necessary reagents and conditions, to achieve the desired transformation efficiently.

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Related Practice

Textbook Question

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

a. CH₃CH₂CH₂Br→CH₃CH₂CH₂CH₂CH₃

Textbook Question

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

Textbook Question

How could the following compounds be synthesized from acetylene?

c. CH₃CH═CH₂

Textbook Question

How could the following compounds be synthesized from acetylene?

Textbook Question

The fragrance of (Z)-1-phenylhex-2-en-1-ol resembles that of roses, with a delicate citrus edge. Show how you would synthesize this compound from benzaldehyde (PhCHO) and any other reagents you need.

Textbook Question

Show how you would convert

d. but-1-yne to cis-hex-3-ene.

Textbook Question

Show how you would synthesize the following compounds from acetylene and any other needed reagents:

(a) 6-phenylhex-1-en-4-yne

(b) cis-1-phenylpent-2-ene

Textbook Question

Muscalure, the sex attractant of the common housefly, is cis-tricos-9-ene. Most syntheses of alkenes give the more stable trans isomer as the major product. Devise a synthesis of muscalure from acetylene and other compounds of your choice. Your synthesis must give specifically the cis isomer of muscalure.

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How could the following compounds be synthesized from acetylene?e.

Key Concepts

Acetylene Reactivity

Functional Group Transformations

Synthetic Pathways

Watch next

How could the following compounds be synthesized from acetylene?
e.