Chloroformates have the functional group \(\mathrm{R}-\mathrm{O} \mathrm{Cl}\), in which \(\mathrm{R}\) is often a tertbutyl or benzyl group. A chloroformate is used in the following synthesis of the antibacterial drug, linezolid (Zyvox). Based on your knowledge of carboxylic acid derivatives, predict the product of the following transformation used in a synthesis of linezolid (Zyvox). The new functional group created is called a carbamate. Carbamates are often used as protecting groups for amine groups during complex syntheses.

Short Answer

Expert verified
Answer: The product of this reaction is a carbamate, with the general structure R-N(H)C(O)R', where R is the group from the amine-containing compound, and R' is the tertbutyl or benzyl group from the chloroformate.

Step by step solution

01

Identify the reaction participants

The reactants of this transformation are a chloroformate compound, with the general structure \(\mathrm{R}-\mathrm{O} \mathrm{Cl}\), and an amine-containing compound. We don't have the specific structures, but we can still work with the general structures.
02

Understand the reactivity of chloroformates

Chloroformates are a type of carboxylic acid derivative. They are electrophilic species that can react with nucleophiles, such as amines. The chlorine atom is a good leaving group due to its high electronegativity, which facilitates the nucleophilic attack.
03

Reaction of chloroformate with an amine

In this step, the nucleophilic nitrogen atom of the amine will attack the electrophilic carbon atom of the chloroformate, resulting in a transfer of the bonding electrons between the carbon and the chlorine atom. The chlorine atom will leave as a chloride ion. The net result is the formation of a new carbon-nitrogen bond between the chloroformate and the amine.
04

Formation of a carbamate functional group

After the bond formation between the amine and the chloroformate, a carbamate group is formed. The general structure of a carbamate is \(\mathrm{R}-\mathrm{N}(\mathrm{H})\mathrm{C}(\mathrm{O})\mathrm{R}'\), where \(\mathrm{R}\) is the molecule containing the amine group, and \(\mathrm{R}'\) is the tertbutyl or benzyl group from the original chloroformate.
05

Final product prediction

Based on the reaction mechanism described above, we predict that the product of this transformation will be a carbamate. The \(\mathrm{R}\) group from the amine-containing compound and the \(\mathrm{R}'\) group from the chloroformate will form the new functional group in the product: \(\mathrm{R}-\mathrm{N}(\mathrm{H})\mathrm{C}(\mathrm{O})\mathrm{R}'\). This carbamate group is often used as a protecting group during complex syntheses, such as the one for linezolid (Zyvox).

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