Chapter 13: Problem 18
Aniline reacts with which of the following to form a Schiff's base: (a) Benzaldehyde (b) Acetone (c) Acetic acid (d) Both (a) and (b)
Short Answer
Expert verified
Aniline reacts with both benzaldehyde and acetone to form Schiff's bases, so the correct answers are (a) Benzaldehyde and (b) Acetone.
Step by step solution
01
Understanding Schiff's Bases
Schiff's bases are typically formed when an amine reacts with an aldehyde or ketone through a condensation reaction, resulting in the release of water and formation of a double bond between nitrogen and carbon (imine formation).
02
Analyzing Option (a) - Benzaldehyde
Benzaldehyde is an aldehyde which can react with aniline to form an imine linkage, thus leading to the formation of a Schiff's base. This is because it has a carbonyl group that is essential for the condensation reaction with an amine.
03
Analyzing Option (b) - Acetone
Acetone is a ketone which can also react with an amine to form a Schiff's base. The carbonyl group present in acetone is reactive towards nucleophilic attack by an amine, leading to imine formation.
04
Analyzing Option (c) - Acetic Acid
Acetic acid does not typically react with amines to form Schiff's bases because it does not contain a carbonyl group that is reactive towards amines in the same way that aldehydes and ketones are. Instead, it forms amides.
05
Conclusion
Aniline can react both with benzaldehyde (an aldehyde) and acetone (a ketone) to form a Schiff's base. Acetic acid does not participate in the formation of such bases with aniline.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Amine and Aldehyde Condensation Reaction
The condensation reaction between an amine and an aldehyde is a fundamental process in organic chemistry that leads to the formation of an imine, often referred to as a Schiff's base. This reaction involves the nucleophilic attack of the nitrogen atom in the amine on the carbonyl carbon of the aldehyde. As the nucleophile (amine) and electrophile (aldehyde) come together, they form an intermediate imine compound through the loss of a water molecule.
This elimination of water is what characterizes it as a condensation reaction. Typically, the reaction mechanism goes through a series of steps, starting with the formation of a carbinolamine intermediate, which then dehydrates to yield the imine product. To facilitate this understanding, it is essential to familiarize oneself with the structure of both reactants - amines having the generic formula 'R-NH2' and aldehydes represented as 'R-CHO' where 'R' can be a variety of alkyl or aryl groups.
This elimination of water is what characterizes it as a condensation reaction. Typically, the reaction mechanism goes through a series of steps, starting with the formation of a carbinolamine intermediate, which then dehydrates to yield the imine product. To facilitate this understanding, it is essential to familiarize oneself with the structure of both reactants - amines having the generic formula 'R-NH2' and aldehydes represented as 'R-CHO' where 'R' can be a variety of alkyl or aryl groups.
- An amine contains a basic nitrogen atom that can donate a pair of electrons.
- An aldehyde has a carbonyl group (C=O) with a partial positive charge on the carbon, making it susceptible to nucleophilic attack.
Imines in Organic Chemistry
In organic chemistry, imines are a class of compounds characterized by the presence of a carbon-nitrogen double bond (C=N), also known as an imine group. The formation of imines is a critical transformation and is involved in a wide variety of synthetic sequences and biological processes.
The creation of an imine, through the reaction between an amine and aldehyde, is a fine illustration of nitrogen's versatility in forming stable multiple bonds with carbon. Because of this reactivity, imines serve as intermediates in many reactions, including the synthesis of amines, alpha-amino acids, and heterocycles. They are also involved in the Strecker synthesis of amino acids and in the Ugi reaction, which is used to produce a wide array of compounds.
As intermediates, imines are often targeted for further transformation. They can undergo:
The creation of an imine, through the reaction between an amine and aldehyde, is a fine illustration of nitrogen's versatility in forming stable multiple bonds with carbon. Because of this reactivity, imines serve as intermediates in many reactions, including the synthesis of amines, alpha-amino acids, and heterocycles. They are also involved in the Strecker synthesis of amino acids and in the Ugi reaction, which is used to produce a wide array of compounds.
As intermediates, imines are often targeted for further transformation. They can undergo:
- Hydrogenation to form amines,
- Reaction with nucleophiles to form carbon-nitrogen bonds, or
- Hydrolysis back to the original aldehyde and amine.
Aniline Reactions
Aniline, an aromatic amine with the formula C6H5NH2, is a significant compound in organic chemistry. Its reactivity is largely governed by the amine group attached to the phenyl ring, which can participate in various reactions, one of which is with carbonyl compounds to form Schiff's bases.
Pivotal to understanding aniline's chemistry is its behavior as a nucleophile due to the lone pair of electrons on the nitrogen atom. When reacting with aldehydes, for instance, the nitrogen atom attacks the partially positive carbonyl carbon leading to the formation of a Schiff's base after water is eliminated.
Pivotal to understanding aniline's chemistry is its behavior as a nucleophile due to the lone pair of electrons on the nitrogen atom. When reacting with aldehydes, for instance, the nitrogen atom attacks the partially positive carbonyl carbon leading to the formation of a Schiff's base after water is eliminated.
Notable Reactions Involving Aniline
Aniline, due to its aromatic amine nature, also readily undergoes:- Electrophilic substitution reactions at the ortho and para positions of the benzene ring,
- Oxidation to form various products, depending on the conditions, and
- Acylation to give anilides, which are amides of aniline.