Acid chlorides can be converted into primary amines with the loss of a single carbon atom via the Curtius rearrangement. The rea
ction involves treating an acid chloride with sodium azide to form an acyl azide. The acyl azide then loses N2 to give an isocyanate, which is hydrolyzed to release CO2 and the primary amine. Draw curved arrows to show the movement of electrons in this step of the mechanism.
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