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

Acetylide

Organic Chemistry

9. Alkenes and Alkynes

Acetylide

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5:06 minutes

Problem 39j

Textbook Question

What is the major product of the reaction of 1 mol of propyne with each of the following reagents?
j. the product of part i followed by 1-chloropropane

Verified step by step guidance

Step 1: Begin by analyzing the reaction in part i. Propyne (CH≡C-CH₃) reacts with the reagent specified in part i. Determine the product formed in part i before proceeding to part j.

Step 2: Once the product of part i is identified, consider the reaction of this product with 1-chloropropane (CH₃-CH₂-CH₂-Cl). This step involves understanding the type of reaction mechanism that will occur, such as nucleophilic substitution or addition.

Step 3: Identify the functional groups present in the product of part i and in 1-chloropropane. Determine how these groups interact chemically, considering factors like electrophilicity, nucleophilicity, and steric hindrance.

Step 4: Predict the major product of the reaction based on the mechanism. For example, if the reaction involves nucleophilic substitution, identify the leaving group and the nucleophile, and predict the structure of the resulting compound.

Step 5: Verify the stability of the major product formed. Consider factors such as resonance stabilization, steric effects, and electronic effects to confirm that the predicted product is indeed the major product of the reaction.

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Key Concepts

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

Alkyne Reactivity

Alkynes, such as propyne, are unsaturated hydrocarbons that contain a carbon-carbon triple bond. This triple bond makes them highly reactive, particularly in addition reactions. Understanding how alkynes react with various reagents is crucial for predicting the products of these reactions, including the formation of alkenes or alkanes depending on the conditions and reagents used.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of the question, 1-chloropropane can act as a nucleophile, and understanding how it interacts with the product from the first reaction is essential for determining the final product. This concept is key in predicting the outcome of reactions involving alkyl halides.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX to an alkene or alkyne, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the regioselectivity of reactions involving propyne and other unsaturated hydrocarbons, guiding the formation of major products when reacting with electrophiles or during nucleophilic substitutions.

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Related Practice

Textbook Question

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

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.]

(a)

Textbook Question

Show how you would accomplish the following synthetic transformations. Show all intermediates.

c. but-1-yne → oct-3-yne

Multiple Choice

Predict the major, organic product of the following reaction.

Textbook Question

What is the major product of the reaction of 1 mol of propyne with each of the following reagents?

i. sodium amide

Textbook Question

Show how you might synthesize the following compounds, using acetylene and any suitable alkyl halides as your starting materials. If the compound given cannot be synthesized by this method, explain why.

a. hex-1-yne

b. hex-2-yne

c. hex-3-yne

Textbook Question

Give two sets of reactants (each set including an alkyl halide and a nucleophile) that could be used to synthesize the following alkyne:

CH₃CH₂C≡CCH₂CH₂CH₂CH₃

Textbook Question

Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]

(a)

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What is the major product of the reaction of 1 mol of propyne with each of the following reagents? j. the product of part i followed by 1-chloropropane

Key Concepts

Alkyne Reactivity

Nucleophilic Substitution

Markovnikov's Rule

Watch next

What is the major product of the reaction of 1 mol of propyne with each of the following reagents?
j. the product of part i followed by 1-chloropropane