Textbook Question
Predict the products of the following reactions.
(a)
(b)
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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 22c,d
Predict the products of the following reactions.
(c) 
(d) 
Verified step by step guidance1
Step 1: Analyze the reaction in part (a). The reactants include a ketone (acetophenone) and an amine (aniline) in the presence of an acid catalyst (H⁺). This is a typical reaction for imine formation, where the carbonyl group reacts with the amine to form a C=N bond.
Step 2: In part (a), the mechanism begins with the protonation of the carbonyl oxygen by H⁺, increasing the electrophilicity of the carbonyl carbon. The amine (PhNH₂) then attacks the carbonyl carbon, forming a tetrahedral intermediate.
Step 3: In part (a), the intermediate undergoes dehydration (loss of water) to form the imine product. The final product will have a C=N bond between the phenyl group of the amine and the carbonyl carbon of acetophenone.
Step 4: Analyze the reaction in part (b). The reactants include an aldehyde (acrolein), hydrazine (H₂N-NH₂), and an acid catalyst (H⁺). This is a typical reaction for hydrazone formation, where the aldehyde reacts with hydrazine to form a C=N bond.
Step 5: In part (b), the mechanism begins with the protonation of the carbonyl oxygen by H⁺, increasing the electrophilicity of the carbonyl carbon. Hydrazine attacks the carbonyl carbon, forming a tetrahedral intermediate. The intermediate undergoes dehydration (loss of water) to form the hydrazone product, which contains a C=N bond between the hydrazine and the aldehyde carbon.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Imine Formation
Imine formation occurs when a carbonyl compound (like an aldehyde or ketone) reacts with a primary amine. The reaction involves the nucleophilic attack of the amine on the carbonyl carbon, followed by the elimination of water. This process is crucial in organic synthesis, as imines can serve as intermediates in various reactions, including condensation and rearrangement.
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Imine Mechanism
Enamine Formation
Enamines are formed when a carbonyl compound reacts with a secondary amine. The reaction involves the nucleophilic attack of the amine on the carbonyl carbon, leading to the formation of a double bond between the nitrogen and the carbon adjacent to the carbonyl. Enamines are valuable intermediates in organic synthesis, particularly in alkylation and acylation reactions.
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Acid-Base Catalysis
Acid-base catalysis plays a significant role in the formation of imines and enamines. The presence of an acid (H+) can protonate the carbonyl oxygen, increasing the electrophilicity of the carbonyl carbon and facilitating the nucleophilic attack by the amine. This catalytic step is essential for enhancing the reaction rate and ensuring the successful formation of the desired products.
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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
Show what amines and carbonyl compounds combine to give the following derivatives.
(d)
611
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Textbook Question
Propose a mechanism for the hydrolysis of benzaldehyde methyl imine just shown.
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Textbook Question
Show what amines and carbonyl compounds combine to give the following derivatives.
(e)
611
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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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