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 23a,b,c
Show what amines and carbonyl compounds combine to give the following derivatives.
(a) 
(b) 
(c) 
Verified step by step guidance1
Step 1: Analyze the given derivatives in the images. Each derivative is formed by the reaction of an amine with a carbonyl compound. Identify the functional groups present in each derivative to deduce the starting materials.
Step 2: For derivative (a), observe the structure. It contains a hydrazone functional group (-C=N-NH2). This suggests that the derivative is formed by the reaction of a hydrazine (H2N-NH2) with an aldehyde or ketone. The carbonyl compound here is likely an aldehyde due to the presence of a hydrogen atom attached to the carbonyl carbon.
Step 3: For derivative (b), observe the structure. It contains an oxime functional group (-C=N-OH). Oximes are formed by the reaction of hydroxylamine (NH2OH) with a carbonyl compound. The cyclic structure indicates that the carbonyl compound is a cyclohexanone.
Step 4: For derivative (c), observe the structure. It contains a Schiff base functional group (-C=N-NHPh). Schiff bases are formed by the reaction of a primary amine (in this case, aniline, NH2Ph) with a carbonyl compound. The cyclic structure indicates that the carbonyl compound is likely cyclopentanone.
Step 5: Summarize the reactions: (a) Hydrazine reacts with an aldehyde to form the hydrazone derivative. (b) Hydroxylamine reacts with cyclohexanone to form the oxime derivative. (c) Aniline reacts with cyclopentanone to form the Schiff base derivative.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Amines
Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can be classified as primary, secondary, or tertiary based on the number of carbon-containing groups attached to the nitrogen atom. Amines are nucleophilic and can react with carbonyl compounds to form imines or enamines, depending on the reaction conditions.
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Reductive Amination
Carbonyl Compounds
Carbonyl compounds contain a carbon atom double-bonded to an oxygen atom (C=O). This functional group is characteristic of aldehydes and ketones, which are key reactants in organic synthesis. The electrophilic nature of the carbonyl carbon allows it to react with nucleophiles, such as amines, leading to the formation of derivatives like imines and enamines through condensation reactions.
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Imines and Enamines
Imines and enamines are derivatives formed from the reaction of amines with carbonyl compounds. Imines are formed when a primary amine reacts with a carbonyl compound, resulting in a C=N bond. Enamines, on the other hand, are formed from secondary amines and feature a C=C bond adjacent to a nitrogen atom. Both structures are important in organic synthesis and can serve as intermediates in various chemical reactions.
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Related Practice
Textbook Question
Predict the products of the following reactions.
(c)
(d)
1350
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Textbook Question
Show what amines and carbonyl compounds combine to give the following derivatives.
(f)
640
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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
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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