Textbook Question
Give the structures of the carbonyl compound and the amine used to form the following imines.
(d)
(e)
(f)
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Ch. 18 - Ketones and Aldehydes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 18, Problem 22a,b
Predict the products of the following reactions.
(a) 
(b) 
Verified step by step guidance1
Step 1: Analyze the reactants and reaction conditions for both parts (a) and (b). In (a), the reactants are cyclohexanone and hydroxylamine (NH2OH) under acidic conditions (H+). In (b), the reactants are bicyclo[2.2.1]heptan-2-one and hydrazine (NH2NH2) under acidic conditions (H+).
Step 2: Recognize the type of reaction occurring. In (a), hydroxylamine reacts with a ketone to form an oxime. This is a condensation reaction where the oxygen of the ketone is replaced by the nitrogen of hydroxylamine. In (b), hydrazine reacts with a ketone to form a hydrazone, which is also a condensation reaction.
Step 3: For (a), the mechanism involves nucleophilic attack by the nitrogen of hydroxylamine on the carbonyl carbon of cyclohexanone, followed by proton transfers and elimination of water to form the oxime. The product will have the structure R-C=N-OH, where R is the cyclohexane ring.
Step 4: For (b), the mechanism involves nucleophilic attack by the nitrogen of hydrazine on the carbonyl carbon of bicyclo[2.2.1]heptan-2-one, followed by proton transfers and elimination of water to form the hydrazone. The product will have the structure R-C=N-NH2, where R is the bicyclo[2.2.1]heptane ring.
Step 5: Verify the stereochemistry and connectivity of the products. Since both reactions involve planar carbonyl groups, the stereochemistry of the products will depend on the orientation of the reactants during the reaction. Ensure the final products are correctly drawn with the appropriate functional groups (oxime for (a) and hydrazone for (b)).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Imine and Enamine Formation
Imine and enamine formation are key reactions in organic chemistry involving the condensation of carbonyl compounds with amines. An imine is formed when a primary amine reacts with a carbonyl compound, resulting in the loss of water. In contrast, enamines are formed from secondary amines and involve a similar condensation process, but with a double bond between the nitrogen and the adjacent carbon.
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Enamine Mechanism
Acid-Catalyzed Reactions
Acid-catalyzed reactions are chemical processes that require an acid to facilitate the reaction. In the context of imine and enamine formation, the presence of an acid (H+) helps protonate the carbonyl oxygen, increasing the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack by the amine. This step is crucial for the successful formation of the desired products.
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Nucleophilic Addition
Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic center, typically a carbonyl carbon. In the reactions presented, the amine acts as the nucleophile, attacking the electrophilic carbon of the carbonyl group. This step is essential for forming the intermediate that ultimately leads to the production of imines or enamines.
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Related Practice
Textbook Question
Show what amines and carbonyl compounds combine to give the following derivatives.
(a)
(b)
(c)
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Textbook Question
Predict the products of the following reactions.
(c)
(d)
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Textbook Question
Show what amines and carbonyl compounds combine to give the following derivatives.
(d)
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Textbook Question
Propose a mechanism for the hydrolysis of benzaldehyde methyl imine just shown.
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Textbook Question
2,4-Dinitrophenylhydrazine is frequently used for making derivatives of ketones and aldehydes because the products (2,4-dinitrophenylhydrazones, called 2,4-DNP derivatives) are even more likely than the phenylhydrazones to be solids with sharp melting points. Propose a mechanism for the reaction of acetone with 2,4-dinitrophenylhydrazine in a mildly acidic solution.
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