Textbook Question
Propose mechanisms for the three imine-forming reactions just shown.
1900
views
Ch. 18 - Ketones and Aldehydes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 19a,b,c
Give the structures of the carbonyl compound and the amine used to form the following imines.
(a) 
(b) 
(c) 
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. The reaction involves the nucleophilic attack of the amine on the carbonyl carbon, followed by dehydration to form the imine.
Step 2: Analyze structure (a). The imine shown has a double bond between the carbon and nitrogen, with two methyl groups attached to the carbon. This indicates that the carbonyl compound used was acetone (CH₃COCH₃), and the amine used was ammonia (NH₃).
Step 3: Analyze structure (b). The imine has a cyclopentyl group attached to the carbon and a CHCH₃ group attached to the nitrogen. This suggests that the carbonyl compound was cyclopentanone (C₅H₈O), and the amine used was ethylamine (CH₃CH₂NH₂).
Step 4: Analyze structure (c). The imine is a cyclic structure with a nitrogen atom incorporated into the ring. This indicates that the carbonyl compound was cyclohexanone (C₆H₁₀O), and the amine used was ammonia (NH₃).
Step 5: Summarize the findings. For each imine: (a) Acetone and ammonia, (b) Cyclopentanone and ethylamine, (c) Cyclohexanone and ammonia. These combinations of carbonyl compounds and amines lead to the respective imines shown in the problem.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
5mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carbonyl Compounds
Carbonyl compounds contain a carbon atom double-bonded to an oxygen atom (C=O). This functional group is pivotal in organic chemistry, as it is involved in various reactions, including the formation of imines. Common examples include aldehydes and ketones, which can react with amines to form imines through a condensation reaction, releasing water.
Recommended video:
Guided course
01:40
Defining meso compounds.
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 carbonyl compounds to form imines. Amines can be classified as primary, secondary, or tertiary based on the number of carbon groups attached to the nitrogen.
Recommended video:
Guided course
07:12Reductive Amination
Imines
Imines are compounds characterized by a carbon-nitrogen double bond (C=N), formed when a carbonyl compound reacts with an amine. This reaction typically involves the nucleophilic attack of the amine on the carbonyl carbon, followed by dehydration. Imines are important intermediates in organic synthesis and can undergo further reactions, such as hydrolysis or reduction.
Recommended video:
Guided course
06:23Imine Mechanism
Related Practice
Textbook Question
Give the structures of the carbonyl compound and the amine used to form the following imines.
(d)
(e)
(f)
1637
views
1
rank
Textbook Question
Show how hex-1-yne might be converted to
d. 1,1,2,2-tetrabromohexane.
962
views
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.
848
views
Textbook Question
Propose a mechanism for the hydrolysis of benzaldehyde methyl imine just shown.
1734
views
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.
937
views