ABSTRACT
Ketones and aldehydes, along with alkenes and alcohols, are among the most common and most used class of organic molecules. Alkyne anions are nucleophiles and they react with alkyl halides to give internal alkynes. Alkyne anions also react as a nucleophile with aldehydes or ketones to give an acyl addition product, the alkoxide. The most common reactions are nucleophilic acyl addition to the carbonyl and acid–base reactions involving protonation of the carbonyl oxygen to form an oxocarbenium ion. The consequence of adding a large excess of water to an acetal is to remove the acetal group, shifting the equilibrium back to the carbonyl group. The product is 1-ethylcyclohexanol where the nucleophilic carbon of the Grignard reagent attacks the electropositive carbonyl carbon, forming a new carbon–carbon bond and producing an alkoxide. A strong carbon–carbon bond is formed when the nucleophilic Grignard reagents attacks the π-bond of the carbonyl.
