Protecting Group
Hardchemistry
Primary amine protecting group often formed as sulfonamide using reagent:
Select the correct option:
Solution
Incorrect! Answer:
p-Toluenesulfonyl chloride (TsCl)
- Reagent: p-Toluenesulfonyl chloride (commonly called Tosyl chloride or TsCl).
- Reaction: R−NH2+Ts−ClPyridineR−NH−Ts+HCl.
- The Product: The result is a Sulfonamide.
- Properties: These groups are used as protecting groups because they are stable under both acidic and basic conditions. They also convert the amine from a nucleophile into a non-nucleophilic species, 'hiding' it during complex synthesis sequences.
- Note: This is also the reagent used in the Hinsberg Test to distinguish between 1∘,2∘, and 3∘ amines.
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About This Question
- Subject
- chemistry
- Chapter
- nitrogen organics
- Topic
- protecting group
- Difficulty
- Hard
- Year
- 2025
Solution
Correct Answer:
p-Toluenesulfonyl chloride (TsCl)
- Reagent: p-Toluenesulfonyl chloride (commonly called Tosyl chloride or TsCl).
- Reaction: R−NH2+Ts−ClPyridineR−NH−Ts+HCl.
- The Product: The result is a Sulfonamide.
- Properties: These groups are used as protecting groups because they are stable under both acidic and basic conditions. They also convert the amine from a nucleophile into a non-nucleophilic species, 'hiding' it during complex synthesis sequences.
- Note: This is also the reagent used in the Hinsberg Test to distinguish between 1∘,2∘, and 3∘ amines.
This hard difficulty chemistry question is from the chapter nitrogen organics, covering the topic of protecting group. It appeared in the 2025 exam.
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