Question

in a synthesis of acetanilide experiment, i performed recrystalization. i used my recovered product to test for impurities. My TLC and melting point analysis seems as if there are no impurities however my nmr shows an impurity maybe consistent with hydrolysis of acetanilide. (50mg was mixed with 400 microliters of deuterated chloroform for NMR) the impurity that im talking about can be seen below with label “figure this out”

is the peak because hydrolysis?

When could have hydrolysis happened and why?

n" (m) 7,28 A (s) 8.51 #H-3 #H-5 H=1 1 3 4 5 6 7 f1 (ppm) O (m, 5H), 2.11 (s, 3H). 6.70- fi9ure out thi 46' F2 TMJ caliDranion andard

Answer 1

Acetanilide singlet at 2.11 ppm CHз H H н H multiplet at 7.28 ppm which integrates 5 H The hydrolysis product H нӧ. CH3 CHЗ н* -CH3 O-H O: -H - H NH2 -CНз CH3 но но -singlet at 2.11 ppm CH3 но аcetic acid singlet at 8.5 ppm probable impurity