protecting group

Question

Primary amine protecting group often formed as sulfonamide using reagent:

RankGuru · Accepted Answer

1. **Reagent**: **$p$-Toluenesulfonyl chloride** (commonly called **Tosyl chloride** or **TsCl**).
2. **Reaction**: $R-NH_2 + Ts-Cl \xrightarrow{Pyridine} R-NH-Ts + HCl$.
3. **The Product**: The result is a **Sulfonamide**.
4. **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.
5. **Note**: This is also the reagent used in the **Hinsberg Test** to distinguish between $1^\circ, 2^\circ,$ and $3^\circ$ amines.

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protecting group

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