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

Oxymercuration

Organic Chemistry

10. Addition Reactions

Oxymercuration

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2:54 minutes

Problem 8d

Textbook Question

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

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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 hydration of alkynes, the addition of water in the presence of an acid catalyst (H₂SO₄) and mercuric sulfate (HgSO₄) leads to the formation of an enol intermediate, which tautomerizes to a ketone.

Consider regioselectivity and stereoselectivity, if applicable. For example, in the hydration of an unsymmetrical alkyne, Markovnikov's rule dictates that the carbon with fewer hydrogens will receive the hydroxyl group, leading to the formation of a specific ketone.

Draw the final product based on the reaction pathway and the reagents used. Ensure that the structure reflects the correct functional group (aldehyde or ketone) and any regioselective or stereoselective outcomes of the reaction.

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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 the carbonyl group at the end of the carbon chain, while ketones have it within the chain. Understanding their structure is crucial for predicting reaction outcomes, as the reactivity of the carbonyl group plays a significant role in various organic reactions.

Nucleophilic Addition Reactions

Nucleophilic addition reactions are fundamental processes in organic chemistry where a nucleophile attacks the electrophilic carbon of a carbonyl group. This reaction is key in the synthesis of aldehydes and ketones, leading to the formation of alcohols or other functional groups. Recognizing the nature of the nucleophile and the conditions of the reaction is essential for predicting the products formed.

Functional Group Transformations

Functional group transformations involve the conversion of one functional group into another through chemical reactions. In the context of aldehyde and ketone syntheses, understanding how to manipulate these groups allows chemists to design pathways to desired products. This concept is vital for predicting the outcome of reactions and for synthesizing complex organic molecules.

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Related Practice

Textbook Question

Would you expect the following to produce an equal or unequal mixture of stereoisomers?

(a)

Textbook Question

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(h)

Textbook Question

For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (vi) H₂SO₄, HgSO₄, H₂O. If you expect two products, show both.

(c)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (ii) 1. Hg(OAc)₂ 2. NaBH₄.If there is no reaction, write 'no reaction.'

(a)

Textbook Question

Would you expect the following to produce an equal or unequal mixture of stereoisomers?

(c)

Textbook Question

Predict the product of each of the following alcohol synthesis reactions.

(a)

Textbook Question

In 1973, Caine and Tuller reported a synthesis of racemic oplapanone, a sesquiterpene isolated from Oplopanax japonicus (a deciduous shrub) involving a reaction we learned in this chapter. Predict the product of the reaction shown. (Caine, D.; Tuller, F. N. J. Org. Chem. 1973, 38, 3663.)

Textbook Question

Assessment 8.74 revealed that oxymercuration could be used to make cyclic esters. Suggest a likely mechanism for this transformation.

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

Key Concepts

Aldehydes and Ketones

Nucleophilic Addition Reactions

Functional Group Transformations

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