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

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

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2:02 minutes

Problem 50l

Textbook Question

Predict the products of the following reactions.
(l)

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Step 1: Identify the functional groups in the reactants. The cyclic compound contains a ketone and an ester functional group. The second reactant is ethylene glycol (HOCH₂CH₂OH), which is a diol (contains two hydroxyl groups). The reaction occurs under acidic conditions (H⁺).

Step 2: Recognize the type of reaction. This is an acetal formation reaction, where a ketone reacts with a diol under acidic conditions to form a cyclic acetal. Acetals are stable compounds often used to protect carbonyl groups in organic synthesis.

Step 3: Understand the mechanism. The reaction begins with protonation of the ketone oxygen by the acid catalyst, making the carbonyl carbon more electrophilic. The diol then attacks the carbonyl carbon, forming a tetrahedral intermediate.

Step 4: The intermediate undergoes proton transfer and elimination of water to form a hemiacetal. The second hydroxyl group of the diol then attacks the hemiacetal carbon, leading to the formation of a cyclic acetal after another elimination of water.

Step 5: Predict the product. The cyclic acetal formed will have the diol incorporated into the structure, with the two oxygen atoms of the diol forming a ring with the original carbonyl carbon. This protects the ketone group in the molecule.

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Key Concepts

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

Acid-Catalyzed Reactions

Acid-catalyzed reactions involve the use of an acid to increase the rate of a chemical reaction. In organic chemistry, acids can protonate reactants, making them more electrophilic and facilitating nucleophilic attacks. This is particularly important in reactions involving alcohols and carbonyl compounds, where the acid can enhance the reactivity of the carbonyl carbon.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically found in carbonyl groups. In this case, the alcohol acts as a nucleophile, attacking the electrophilic carbon of the cyclic compound's carbonyl, leading to the formation of a new bond and the potential for product formation.

Cyclic Compounds and Ring Strain

Cyclic compounds are molecules that contain a ring structure, which can introduce ring strain depending on the size and substituents of the ring. In the context of the reaction, the cyclic compound may have specific steric and electronic properties that influence its reactivity with the alcohol. Understanding the stability and strain of the ring is crucial for predicting the outcome of the reaction.

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Related Practice

Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(e) cyclohexylamine → N-cyclohexylacetamide

(f) bromocyclohexane → dicyclohexylmethanol

Textbook Question

Predict the products of the following reactions.

(a)

Textbook Question

Predict the products of the following reactions.

(b)

Textbook Question

Predict the products of the following reactions.

(k)

Textbook Question

Show how you would accomplish the following syntheses in good yields.

(g)

Textbook Question

Propose a mechanism for the reaction of benzyl acetate with methylamine. Label the attacking nucleophile and the leaving group, and draw the transition state in which the leaving group leaves.

Textbook Question

1. Propose a mechanism for the acid-catalyzed reaction of salicylic acid with acetic anhydride.

2. Explain why a single drop of sulfuric acid dramatically increases the reaction rate.

Textbook Question

Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.

(d) succinic acid monomethyl ester

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Predict the products of the following reactions.(l)

Key Concepts

Acid-Catalyzed Reactions

Nucleophilic Addition

Cyclic Compounds and Ring Strain

Watch next

Predict the products of the following reactions.
(l)