H3C 1. NaN3 2. H₂O, heat H3C CI Acid chlorides can be converted into primary amines with the loss of a single carbon atom via the Curtius rearrangement. The reaction involves treating an acid chloride with sodiur 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. Arrow-pushing Instructions →X™ NH H :A CH3NH2 + CO₂ H-A N₂ + NaCl HạC—NH, CO₂ H-A :A

H3C 1. NaN3 2. H₂O, heat H3C CI Acid chlorides can be converted into primary amines with the loss of a single carbon atom via the Curtius rearrangement. The reaction involves treating an acid chloride with sodiur 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. Arrow-pushing Instructions →X™ NH H :A CH3NH2 + CO₂ H-A N₂ + NaCl HạC—NH, CO₂ H-A :A

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.59P

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