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 19d,e,f
Give the structures of the carbonyl compound and the amine used to form the following imines.
(d) 
(e) 
(f) 
Verified step by step guidance1
Step 1: Understand the reaction that forms imines. Imines are formed by the condensation reaction between a carbonyl compound (aldehyde or ketone) and a primary amine. During this reaction, the oxygen from the carbonyl group is replaced by the nitrogen from the amine, forming a C=N bond.
Step 2: Analyze structure (a). The imine shown has a C=N bond within a bicyclic structure. To deduce the starting materials, identify the carbon atom bonded to the nitrogen in the imine. This carbon was originally part of a carbonyl group (likely a ketone). The nitrogen atom came from a primary amine. The carbonyl compound would be cyclohexanone, and the amine would be cyclohexylamine.
Step 3: Analyze structure (b). The imine shown has a C=N bond within a bicyclic structure similar to (a). The carbonyl compound would again be cyclohexanone, but the amine would be a different primary amine, specifically cyclohexylamine with a different substitution pattern.
Step 4: Analyze structure (c). The imine shown has a C=N bond attached to a benzene ring and a methyl group on the nitrogen. The carbonyl compound would be benzaldehyde (an aldehyde with a benzene ring), and the amine would be methylamine (a primary amine with a single methyl group).
Step 5: Summarize the process. For each imine, identify the carbonyl compound and the amine by analyzing the structure of the imine and tracing back to the original reactants. This involves recognizing the C=N bond and determining the source of the carbon and nitrogen atoms in the imine.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carbonyl Compounds
Carbonyl compounds are organic molecules characterized by the presence of a carbonyl group (C=O). This functional group is pivotal in organic chemistry as it participates in various reactions, including nucleophilic addition, which is essential for forming imines. Common examples include aldehydes and ketones, which can react with amines to produce imines.
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Defining meso compounds.
Imines
Imines are a class of compounds formed by the reaction of a carbonyl compound with an amine, resulting in a C=N bond. This reaction typically involves the nucleophilic attack of the amine on the carbonyl carbon, followed by the elimination of water. Imines are important intermediates in organic synthesis and can be further transformed into various functional groups.
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Amines
Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can act as nucleophiles due to the lone pair of electrons on the nitrogen atom, allowing them to react with electrophiles such as carbonyl compounds. Understanding the structure and reactivity of amines is crucial for predicting their behavior in imine formation.
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Related Practice
Textbook Question
Show how hex-1-yne might be converted to
d. 1,1,2,2-tetrabromohexane.
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Textbook Question
Give the structures of the carbonyl compound and the amine used to form the following imines.
(a)
(b)
(c)
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Textbook Question
Depending on the reaction conditions, two different imines of formula C8H9N might be formed by the reaction of benzaldehyde with methylamine. Explain, and give the structures of the two imines.
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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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