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

10. Addition Reactions

Alkyne Hydroboration

Organic Chemistry

10. Addition Reactions

Alkyne Hydroboration

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2:20 minutes

Problem 46a

Textbook Question

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

Verified step by step guidance

Identify the target compound structure from the image and determine the functional groups present. This will help in planning the synthetic route from ethyne.

Recognize that ethyne (C₂H₂) is a simple alkyne with a triple bond, which can undergo various reactions such as addition, substitution, and oxidation to form different functional groups.

Consider the addition of hydrogen (hydrogenation) to ethyne to form ethene (C₂H₄) or ethane (C₂H₆), depending on the degree of hydrogenation. This step is crucial if the target compound contains single or double bonds.

If the target compound contains a halogen, consider halogenation reactions. Ethyne can react with halogens like Br₂ or Cl₂ to form dihaloalkenes or tetrahaloalkanes, depending on the reaction conditions.

For the introduction of functional groups such as alcohols, aldehydes, or ketones, consider hydroboration-oxidation or hydration reactions. Ethyne can be converted to an aldehyde or ketone through hydroboration followed by oxidation, or to an alcohol through hydration.

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Key Concepts

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

Ethyne as a Building Block

Ethyne, also known as acetylene, is a simple alkyne that serves as a versatile building block in organic synthesis. Its triple bond allows for various reactions, including addition reactions with electrophiles, which can lead to the formation of more complex molecules. Understanding how to manipulate ethyne's reactivity is crucial for synthesizing target compounds.

Reactions of Alkynes

Alkynes undergo a variety of chemical reactions, including hydrogenation, halogenation, and hydroboration. These reactions can modify the triple bond to form double bonds or single bonds, allowing for the construction of different functional groups. Familiarity with these reaction mechanisms is essential for predicting the products when starting from ethyne.

Functional Group Transformations

Functional group transformations involve converting one functional group into another, which is a key strategy in organic synthesis. By understanding how to perform these transformations, such as converting alkynes to alcohols or ketones, chemists can design pathways to synthesize desired compounds from ethyne. This concept is fundamental for planning synthetic routes in organic chemistry.

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Related Practice

Textbook Question

Predict the products of reaction of pent-1-yne with the following reagents.

j. NaNH₂

k. H₂SO₄/HgSO₄, H₂O

l. Sia₂BH, then H₂O₂, ^–OH

Textbook Question

Draw the ketone(s) you would expect to form by treating the following alkynes under the conditions of hydroboration–oxidation: (a) 6-methyloct-1-yne, (b) 1,10-dicyclohexyldec-5-yne, and (c) 5-phenylhex-2-yne.

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Textbook Question

For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (vii) 1. BH₃ 2. H₂O₂, NaOH. If you expect two products, show both.

(c)

Textbook Question

Predict the product of the following aldehyde/ketone syntheses.

(c)

Textbook Question

What are products of the following reactions?

Textbook Question

The following functional-group interchange is a useful synthesis of aldehydes.

(a) What reagents were used in this chapter for this transformation? Give an example to illustrate this method.

(b) This functional-group interchange can also be accomplished using the following sequence.

Propose mechanisms for these steps.

Textbook Question

For each of the following alkynes, draw the products obtained from (1) the acid-catalyzed addition of water (mercuric ion is added for part a) and from (2) hydroboration–oxidation:

a. 1-butyne

Textbook Question

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

e. aqueous H₂SO₄, HgSO₄

f. R₂BH in THF followed by H₂O₂/HO⁻/H₂O

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