Chapter 10: Problem 10
Each of the following reaction types occurs during the Gabriel synthesis EXCEPT: a. decarboxylation. b. nucleophilic substitution. c. dehydration. d. hydrolysis.
Short Answer
Expert verified
c. dehydration.
Step by step solution
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
primary amines synthesis
The Gabriel synthesis is a popular method used to synthesize primary amines.
Primary amines are compounds that contain an -NH2 group, connected to an alkyl or aryl group. Gabriel synthesis takes a special approach to avoid over-alkylation, which is common in simpler methods.
To create these amines, the process starts with potassium phthalimide reacting with an alkyl halide. This initial step forms an N-alkyl phthalimide intermediate.
Thereafter, this intermediate undergoes hydrolysis and decarboxylation to finally yield a primary amine.
Primary amines are compounds that contain an -NH2 group, connected to an alkyl or aryl group. Gabriel synthesis takes a special approach to avoid over-alkylation, which is common in simpler methods.
To create these amines, the process starts with potassium phthalimide reacting with an alkyl halide. This initial step forms an N-alkyl phthalimide intermediate.
Thereafter, this intermediate undergoes hydrolysis and decarboxylation to finally yield a primary amine.
nucleophilic substitution
One of the most vital steps in Gabriel synthesis is nucleophilic substitution.
Nucleophilic substitution is a reaction where a nucleophile, which is a chemical species that donates an electron pair, replaces a leaving group in a molecule.
In the Gabriel synthesis, potassium phthalimide serves as the nucleophile.
The target for this nucleophile is the alkyl halide.
When potassium phthalimide attacks the alkyl halide, it results in the formation of the N-alkyl phthalimide intermediate.
This step is crucial for introducing the alkyl group to the nitrogen atom.
Nucleophilic substitution is a reaction where a nucleophile, which is a chemical species that donates an electron pair, replaces a leaving group in a molecule.
In the Gabriel synthesis, potassium phthalimide serves as the nucleophile.
The target for this nucleophile is the alkyl halide.
When potassium phthalimide attacks the alkyl halide, it results in the formation of the N-alkyl phthalimide intermediate.
This step is crucial for introducing the alkyl group to the nitrogen atom.
hydrolysis
Hydrolysis is another integral step in the Gabriel synthesis.
Hydrolysis is a chemical process where water is used to break down compounds.
For the Gabriel synthesis, hydrolysis happens in two parts: breaking the phthalimide ring and converting the intermediate to the final amine product.
The hydrolytic conditions break the bond between the nitrogen and the carbon atoms in the ring, forming phthalic acid and releasing the primary amine.
This step ensures that the amine is free from the phthalimide group, completing the synthesis.
Hydrolysis is a chemical process where water is used to break down compounds.
For the Gabriel synthesis, hydrolysis happens in two parts: breaking the phthalimide ring and converting the intermediate to the final amine product.
The hydrolytic conditions break the bond between the nitrogen and the carbon atoms in the ring, forming phthalic acid and releasing the primary amine.
This step ensures that the amine is free from the phthalimide group, completing the synthesis.
decarboxylation
Decarboxylation is the removal of a carboxyl group from a molecule, releasing carbon dioxide (CO2).
In Gabriel synthesis, decarboxylation occurs during the hydrolysis step.
When N-alkyl phthalimide undergoes hydrolysis, it breaks down into phthalic acid and a primary amine.
During this step, the removal of the carboxyl group as CO2 happens, leading to the simplification of the intermediate into the desired primary amine.
This step is necessary to obtain a pure primary amine at the end of the synthesis.
In Gabriel synthesis, decarboxylation occurs during the hydrolysis step.
When N-alkyl phthalimide undergoes hydrolysis, it breaks down into phthalic acid and a primary amine.
During this step, the removal of the carboxyl group as CO2 happens, leading to the simplification of the intermediate into the desired primary amine.
This step is necessary to obtain a pure primary amine at the end of the synthesis.
