Scrabble?! CYANOETHYLATION

Definitions of CYANOETHYLATION in various dictionaries:

Cyanethylation is a nucleophilic addition reaction. A molecule of acrylonitrile is added to a nucleophile, for example an alcohol, thiol or an amine. Y H + H 2 C = C H − C N ⟶ Y − C H 2 − C H 2 − C N {\displaystyle \mathrm {YH+H_{2}C{=}CH{-}CN\longrightarrow Y{-}CH_{2}{-}CH_{2}{-}CN} } Due to the mesomeric stabilization of acrylonitrile and the electron withdrawing nitrile group, the β-carbon atom (the carbon atom that is furthest from the nitrile group) is positively polarized and therefore acts as a Michael acceptor. This leads to an approaching of the nucleophile to the β-carbon atom, which initiates the reaction. The reaction is terminated by absorption of a proton from the solvent by the intermediate product. In industrial applications, the reaction is normally catalyzed by a base that polarizes or (negatively) charges the nucleophile and thus accelerates the reaction.Cyanethylation is used especially in the industrial pharmaceutical and dye sector, since this reaction extends the nucleophile bearing molecule by three carbon atoms plus the -C≡N bond can afterwards be removed or modified by (for example) reduction. Cyanethylation is also used in technical polymerization. If cyanethylation takes place in a medium that cannot release a proton to the product at the end of the reaction, an anionic polymerization occurs. Due to the lack of protonation, the α-carbon atom remains negatively charged, causing the individual cyanethylation products to polymerise.