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May 6, 2024

Organic chemistry- must draw out the mechanism

draw the mechanism of amide molecule CH3CONH2 with thionyl chloride (SOCl2). The reaction should include all intermediate steps, proper electron arrow movement, lone pairs, and charges. Must draw out the mechanism, don’t just write it out. Draw the molecule, show arrow movements and lone pair

Oxygen attack on sulfur opening the S=O bond and releasing a Cl anion atom – Missing the pi bond to the carbonyl. Lone pair in N forming double bond with carbonyl carbon and opening pi bond with carbonyl oxygen to reestablishing a neutral charge on the oxygen. Cl anion in amides will deprotonate – essential step that is different here due to acidity of the H on a positively charged N to establish a neutral N atom. The lone pair available on the N can add to the pi system to form the triple bond for a nitrile releasing the O-SSOCl fragement. of the H on the N to form a triple bond by -O-SOCl anion to form nitrile

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