Acrolein (H2C CHCH O) reacts with sodium azide (NaN3) in aqueous acetic acid to form a

Chapter 20, Problem 20.25

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Acrolein (H2C CHCH O) reacts with sodium azide (NaN3) in aqueous acetic acid to form a compound, C3H5N3O in 71% yield. Propanal (CH3CH2CH O), when subjected to the same reaction conditions, is recovered unchanged. Suggest a structure for the product formed from acrolein, and offer an explanation for the difference in reactivity between acrolein and propanal.

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