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Question 47 of 69

Q.How is methyl cyanide obtained from acetamide ?

Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2017Subjective· 3mImportance★★★★★
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Amides are converted to nitriles by dehydration; a strong dehydrating agent like P2O5P_2O_5 removes a molecule of water from acetamide to give methyl cyanide.

Reaction: Acetamide (CH3CONH2CH_3CONH_2) is heated with a dehydrating agent — commonly phosphorus pentoxide (P2O5P_2O_5), though ZnCl2ZnCl_2 or POCl3POCl_3 can also be used — which abstracts a molecule of water from the amide:

CH3−C(=O)−NH2→heatP2O5CH3−C≡N+H2OCH_3-C(=O)-NH_2 \xrightarrow[\text{heat}]{P_2O_5} CH_3-C\equiv N + H_2O

The product is methyl cyanide, also called acetonitrile (CH3CNCH_3CN), a nitrile.

Mechanism (brief): P2O5P_2O_5 is a powerful dehydrating agent; it removes the elements of water (−H-H from N and −OH-OH equivalent from the carbonyl oxygen) from the amide functional group −CONH2-CONH_2, converting the C=OC=O/C−NH2C-NH_2 system into the C≡NC\equiv N (nitrile) triple bond, with loss of H2OH_2O.

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