Carbonyl compounds undergo a variety of nucleophilic reactions. Which of the following derivatives of cyclohexanone is formed strictly via a nucleophilic addition mechanism, without any subsequent elimination of a small molecule like water?

Step-by-step solution

The formation of cyclohexanone cyanohydrin involves the reaction of cyclohexanone with hydrogen cyanide (HCN). The cyanide ion ( CN^- ) acts as a nucleophile and attacks the electrophilic carbonyl carbon, forming a tetrahedral alkoxide intermediate. This intermediate is then protonated to yield the cyanohydrin. The entire process is a pure nucleophilic addition reaction, and no small molecule like water is eliminated. In contrast, the formation of cyclohexanone oxime (from hydroxylamine), cyclohexanone semicarbazon