The reactions of calcium carbide with cyclohexanone in the presence of potassium hydroxide in toluene, hexanes, and naphthalene-hexanes solvent systems

• Main Authors: Avila, Jose Carlo B., Tenido, Peter Immanuel DL
• Format: text
• Language: English
• Published: Animo Repository 2011
• Online Access: https://animorepository.dlsu.edu.ph/etd_bachelors/10461
• Institution: De La Salle University

The reaction of calcium carbide, CaC2, with two equivalents of cyclohexanone in the presence of potassium hydroxide, KOH, in toluene solvent produced the acetylenic diol, 1,1-ethyne-1,2-diyldicylohexanole in 6.1% yield, while the same reaction done in hexanes produced the acetylenic diol in 5.7% yield. Interestingly, the reaction in naphthalene-hexanes produced a crystalline product previously unreported in similar reactions. Mass and infrared spectra were used to identify the new crystalline product as 1-hydroxy-1,1’:’,13-ter(cyclohexan)-13(3’)-en-2’-one, a product formed by aldol condensations. Physical observations of the reactions as they proceeded may indicate that the reaction proceeds through the formation of a complex, evidenced by intense changes in color and solid formation upon the addition of cyclohexanone, although the nature, structure, and properties of the complexes were no longer studied. The study was based on the assumption that solvent capable of forming coordination bonds with cations facilitate the reaction, although present results cannot conclude as to whether this hypothesis is correct.