Upon heating 2-chloropropanoyl chloride with concentrated ammonia in a sealed vessel, a primary amide is formed but the chlorine atom at the beta carbon does not get substituted with an amino group, that is, the alkyl chloride portion of the molecule fails to undergo nucleophilic substitution.

Why is this so?

  • 1
    $\begingroup$ I'm guessing that the α-carbon is much more eletcophilic than the β-carbon, due to the presence of oxygen and the chlorine, so that leads nitrogen, to transform the 2-chloropropanoyl chloride to the corresponding amide rather than amine. $\endgroup$ – Αντώνιος Κελεσίδης Jul 22 '17 at 20:20

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