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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4:17 minutes

Problem 8c

Textbook Question

Predict the product of the following aldehyde/ketone syntheses.
(c)

Verified step by step guidance

Identify the starting materials and reagents used in the synthesis. Aldehyde and ketone syntheses often involve specific reactions such as oxidation of alcohols, hydration of alkynes, or Friedel-Crafts acylation.

Determine the functional group transformations involved. For example, if the starting material is a primary alcohol, it can be oxidized to an aldehyde using reagents like PCC (Pyridinium chlorochromate). If it is a secondary alcohol, it can be oxidized to a ketone using reagents like chromic acid (H₂CrO₄).

Analyze the reaction mechanism. For instance, in the oxidation of alcohols, the hydroxyl group is converted into a carbonyl group through the loss of hydrogen atoms and the addition of oxygen.

Consider any regioselectivity or stereoselectivity in the reaction. For example, in the hydration of alkynes, the Markovnikov or anti-Markovnikov rule may dictate the position of the carbonyl group in the product.

Draw the structure of the predicted product based on the reaction type, starting material, and reagents. Ensure that the product contains the correct functional group (aldehyde or ketone) and that the carbon skeleton remains consistent with the starting material.

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Key Concepts

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

Aldehydes and Ketones

Aldehydes and ketones are organic compounds characterized by the presence of a carbonyl group (C=O). Aldehydes have at least one hydrogen atom attached to the carbonyl carbon, while ketones have two carbon groups attached. Understanding their structure is crucial for predicting reaction products in organic synthesis.

Nucleophilic Addition Reactions

Nucleophilic addition reactions are fundamental in organic chemistry, particularly for carbonyl compounds. In these reactions, a nucleophile attacks the electrophilic carbon of the carbonyl group, leading to the formation of a tetrahedral intermediate. This process is key to predicting the products formed when aldehydes or ketones react with various nucleophiles.

Synthesis Pathways

Synthesis pathways refer to the step-by-step methods used to create organic compounds from simpler substances. In the context of aldehyde and ketone syntheses, understanding different pathways, such as oxidation of alcohols or reactions with Grignard reagents, is essential for predicting the final products. Familiarity with these pathways allows chemists to design efficient synthetic routes.

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Related Practice

Textbook Question

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

j. trans-hex-2-ene → cis-hex-2-ene

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

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

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

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Predict the product of the following aldehyde/ketone syntheses.(c)

Key Concepts

Aldehydes and Ketones

Nucleophilic Addition Reactions

Synthesis Pathways

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Predict the product of the following aldehyde/ketone syntheses.
(c)