Chapter 10: Problem 9
During the Gabriel synthesis, phthalimide serves as the: a. nucleophile. b. base. c. leaving group. d. electrophile.
Short Answer
Expert verified
a. nucleophile
Step by step solution
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Phthalimide
In the Gabriel synthesis, phthalimide is a crucial reagent. It is an organic compound that contains a nitrogen atom, making it highly reactive when converted into its anion form.
When phthalimide reacts with a strong base like potassium hydroxide (KOH), it forms the phthalimide anion, a powerful nucleophile. This anion is highly reactive and ready to engage in further chemical reactions.
Phthalimide itself is quite stable, but its derivative, the phthalimide anion, is what actually participates in the Gabriel synthesis, attacking the alkyl halide to eventually form the desired primary amine.
Understanding the role of phthalimide sets the stage for grasping the entire Gabriel synthesis process.
When phthalimide reacts with a strong base like potassium hydroxide (KOH), it forms the phthalimide anion, a powerful nucleophile. This anion is highly reactive and ready to engage in further chemical reactions.
Phthalimide itself is quite stable, but its derivative, the phthalimide anion, is what actually participates in the Gabriel synthesis, attacking the alkyl halide to eventually form the desired primary amine.
Understanding the role of phthalimide sets the stage for grasping the entire Gabriel synthesis process.
Primary Amine Synthesis
The Gabriel synthesis is specifically designed to produce primary amines. Here’s a step-by-step breakdown:
This process is highly efficient and avoids complications like polysubstitution, making it an excellent method for synthesizing pure primary amines.
The Gabriel synthesis is often preferred in organic chemistry because it provides a clear, straightforward pathway for creating primary amines from relatively simple starting materials.
- First, phthalimide reacts with a strong base (like KOH), converting it into the phthalimide anion.
- Next, this anion reacts with an alkyl halide. The alkyl group from the alkyl halide replaces one hydrogen on the nitrogen atom.
- The resulting compound is N-alkylphthalimide.
- Finally, hydrolysis breaks the N-alkylphthalimide, yielding the primary amine and phthalic acid.
This process is highly efficient and avoids complications like polysubstitution, making it an excellent method for synthesizing pure primary amines.
The Gabriel synthesis is often preferred in organic chemistry because it provides a clear, straightforward pathway for creating primary amines from relatively simple starting materials.
Nucleophile
A nucleophile is a chemical species that donates an electron pair to form a chemical bond in reaction. In the context of the Gabriel synthesis, the phthalimide anion serves as a strong nucleophile.
Nucleophiles are characterized by their high electron density and their ability to attack electrophiles (electron-deficient atoms). Here’s how nucleophiles like the phthalimide anion work in the Gabriel synthesis:
Understanding the role of nucleophiles helps clarify why phthalimide is so effective in the Gabriel synthesis for producing primary amines.
The strength of the nucleophile often determines the efficiency of the entire synthesis process, making it a key concept in organic chemistry.
Nucleophiles are characterized by their high electron density and their ability to attack electrophiles (electron-deficient atoms). Here’s how nucleophiles like the phthalimide anion work in the Gabriel synthesis:
- The phthalimide anion, rich in electrons, seeks out an alkyl halide because the carbon atom bonded to the halide is electron-poor.
- This interaction allows the phthalimide anion to replace the halide, forming a new carbon-nitrogen bond.
- The result is a stable N-alkylphthalimide, which can be further processed to yield a primary amine.
Understanding the role of nucleophiles helps clarify why phthalimide is so effective in the Gabriel synthesis for producing primary amines.
The strength of the nucleophile often determines the efficiency of the entire synthesis process, making it a key concept in organic chemistry.
