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

13. Alcohols and Carbonyl Compounds

Nucleophilic Addition

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Nucleophilic Addition

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2:38 minutes

Problem 12b

Textbook Question

Predict the product of the following aldehyde and ketone addition reactions.
(b)

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Identify the functional groups present in the reactants. Aldehydes and ketones both contain a carbonyl group (C=O).

Determine the type of addition reaction. Aldehydes and ketones typically undergo nucleophilic addition reactions due to the electrophilic nature of the carbonyl carbon.

Identify the nucleophile in the reaction. Common nucleophiles include hydride ions (H-) from reducing agents or organometallic reagents like Grignard reagents (R-MgX).

Consider the mechanism of the reaction. The nucleophile will attack the electrophilic carbonyl carbon, leading to the formation of a tetrahedral intermediate.

Predict the final product. The addition of the nucleophile to the carbonyl group will result in the formation of an alcohol if the nucleophile is a hydride or an alkoxide if the nucleophile is an organometallic reagent.

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Key Concepts

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

Aldol Condensation

Aldol condensation is a reaction between aldehydes and ketones that involves the formation of a β-hydroxy aldehyde or ketone. This reaction occurs when an enolate ion, generated from a carbonyl compound, attacks another carbonyl carbon, leading to the formation of a new carbon-carbon bond. The product can further dehydrate to yield an α,β-unsaturated carbonyl compound.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom in a carbonyl group. This process is crucial in the formation of alcohols, aldehydes, and ketones. Understanding the reactivity of carbonyl compounds and the nature of nucleophiles is essential for predicting the products of reactions involving aldehydes and ketones.

Reaction Mechanism

A reaction mechanism is a step-by-step description of the pathway taken during a chemical reaction. It outlines the sequence of elementary steps, including bond breaking and forming, that lead to the final products. Analyzing the mechanism helps in predicting the products of reactions involving aldehydes and ketones, as it provides insight into the intermediates and transition states formed during the reaction.

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Related Practice

Textbook Question

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(c)

Textbook Question

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(b)

Textbook Question

Show how you would accomplish the following syntheses.

b. cyclopentanecarbaldehyde → 2-cyclopentyl-2-hydroxyacetic acid

Textbook Question

Propose a mechanism for the following reactions:

Textbook Question

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

(a)

Textbook Question

Classify the following nucleophiles as strong, weak, or intermediate. Would you expect each to add to a carbonyl directly or wait for a carbocation to form?

(d)

Textbook Question

Based on the analysis you used in Assessment 17.3, which carbonyl would you expect to react most quickly with a nucleophile?

(a)

Textbook Question

Why is a ketone more reactive/electrophilic than an ester?

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