Haloalkanes And Haloarenes Test

Result

Haloalkanes And Haloarenes Test - 9

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Question 1
1 / -0

When methyl iodide is treated with NaCN in ethanol, the major organic product is ______ that is generated through an ______ mechanism.

A
CH₃CN, S_N²

B
CH₃NC, S_N¹

C
CH₃NC, S_N²

D
None of these

Solution

Methyl iodide being a primary alkyl halide will undergo nucleophilic substitution by S_N² even though polar protic solvents are not as effective for S_N² reaction as polar aprotic ones because the molecule is stearically unhindered; moreover, 1^o carbocation is not stable.

– CN is an excellent ambident nucleophile, but the product formed is a cyanide instead of an isocyanide as the C-C bond is more stable than the C-N bond. Hence, the product is CH₃CN.