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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2:42 minutes

Problem 15

Textbook Question

What hydrocarbon would you use to prepare the organoboron compound in Problem 14?

Verified step by step guidance

Analyze the structure of the organoboron compound provided in the image. The compound contains a boron atom bonded to two oxygen atoms in a cyclic structure (a catechol group) and a hydrocarbon chain attached to the boron atom.

Identify the hydrocarbon chain attached to the boron atom. In this case, the chain is a straight alkyl chain with five carbon atoms and a double bond between the second and third carbons, indicating it is 1-pentene.

Recall the hydroboration reaction mechanism, which involves the addition of borane (BH3) or a boron-containing reagent to an alkene. The boron atom adds to the less substituted carbon of the double bond, following anti-Markovnikov regioselectivity.

Determine the hydrocarbon needed for the reaction. Since the organoboron compound has a pentyl group with a double bond, the starting hydrocarbon should be 1-pentene, which will react with a boron reagent such as catecholborane.

Conclude that the hydrocarbon required to prepare the organoboron compound is 1-pentene, which undergoes hydroboration with catecholborane to yield the desired product.

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Key Concepts

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

Hydrocarbons

Hydrocarbons are organic compounds consisting entirely of hydrogen and carbon atoms. They serve as the fundamental building blocks for many organic reactions, including those involving organoboron compounds. Understanding the structure and reactivity of different types of hydrocarbons, such as alkanes, alkenes, and alkynes, is crucial for selecting the appropriate substrate for synthesis.

Organoboron Compounds

Organoboron compounds are organic molecules that contain boron atoms bonded to carbon. They are important intermediates in organic synthesis, particularly in cross-coupling reactions like the Suzuki reaction. Knowledge of how to prepare and utilize these compounds is essential for solving problems related to organic synthesis and reactivity.

Synthesis Strategies

Synthesis strategies in organic chemistry involve the methods and pathways used to create specific compounds from simpler starting materials. This includes understanding functional group transformations, reactivity patterns, and the selection of appropriate reagents. A solid grasp of these strategies is necessary to determine which hydrocarbon can effectively yield the desired organoboron compound.

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Related Practice

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

Textbook Question

a. Explain why a single pure product is obtained from hydroboration–oxidation of 2-butyne, whereas two products are obtained from hydroboration–oxidation of 2-pentyne.

b. Name two other internal alkynes that yield only one product upon hydroboration–oxidation.

Textbook Question

What are products of the following reactions?

Multiple Choice

Predict the major, organic product for the following reaction.

Textbook Question

Answer Problem 39, parts a–h, using 2-butyne as the starting material instead of propyne.

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

Textbook Question

Predict the major products of the following reactions.

d. trans-cyclodecene + peroxyacetic acid in acidic water

e. cis-cyclodecene + mCPBA in CH₂Cl₂, then dilute aqueous acid