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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3:15 minutes

Problem 28d

Textbook Question

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

Verified step by step guidance

Step 1: Begin with acetylene (C≡CH), a simple alkyne. The goal is to transform this molecule into the target compound, which is 2,2-dichloro-3,3-dimethylbutane.

Step 2: Perform a reaction to convert acetylene into a substituted alkyne. React acetylene with methyl iodide (CH3I) in the presence of a strong base like sodium amide (NaNH2). This will yield propyne (CH≡CCH3).

Step 3: Carry out a second alkylation reaction to further substitute the alkyne. React propyne with another equivalent of methyl iodide (CH3I) in the presence of NaNH2 to form 2-butyne (CH3C≡CCH3).

Step 4: Hydrogenate the alkyne to form the corresponding alkane. Use a Lindlar catalyst for partial hydrogenation to form 2-butene (CH3CH=CHCH3), or use a standard catalyst like Pd/C for complete hydrogenation to form butane (CH3CH2CH2CH3).

Step 5: Add chlorine atoms to the molecule. React the alkane or alkene with chlorine gas (Cl2) under UV light or appropriate conditions to form the desired compound, 2,2-dichloro-3,3-dimethylbutane. Ensure the reaction conditions favor substitution at the correct positions.

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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 simple alkyne that can undergo various reactions due to its triple bond. It can participate in addition reactions, where reagents add across the triple bond, and can also be used in coupling reactions to form larger carbon frameworks. Understanding the reactivity of acetylene is crucial for determining how to synthesize more complex compounds from it.

Functional Group Transformations

Functional group transformations involve changing one functional group in a molecule to another, which is essential in organic synthesis. This concept is important when synthesizing compounds from acetylene, as it may require converting the alkyne into alcohols, aldehydes, or other functional groups through various reactions like hydroboration, oxidation, or halogenation.

Synthetic Pathways

Synthetic pathways refer to the step-by-step methods used to construct a target molecule from simpler starting materials. In the context of synthesizing compounds from acetylene, it is important to outline a logical sequence of reactions that efficiently build the desired structure, taking into account the necessary reagents, conditions, and potential side reactions.

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Related Practice

Textbook Question

Show how the following compounds can be synthesized starting with ethyne:

b. trans-3-heptene

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

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