The photoreactions of benzaldehyde in benzene, ethanol, and 1-hexyne have been studied. Irradiation of benzaldehyde in benzene produces benzoin (I), hydrobenzoin (II), and deoxybenzoin (III). Irradiation of benzoin (I) in this solvent results in benzaldehyde formation as well as small amounts of (II) and (III). The ethanol irradiation of benzaldehyde resulted, predominantly, in the formation of (II) with (I) formed in small amounts. The photolysis of benzaldehyde in 1-hexyne produces (I), (II), (III) cis-2-heptenophenone (VII), trans-2-heptenophenone (VIII), heptanophenone (IX), and 2-(n-butyl)- 1,4-diphenyl-1,4-butanedione (X). Mechanistic pathways for the formation of these photoproducts are discussed. Separation and characterization of cis- and trans-2- heptenophenone was accomplished. The photoisomerization of these two isomers results in the formation of cis-2-heptenophenone in 94 per cent yield.
College and Department
Chemistry and Biochemistry
BYU ScholarsArchive Citation
Knudsen, Ronald Douglas, "The solution photochemistry of benzaldehyde in benzene, ethanol, and 1-hexyne" (1974). Theses and Dissertations. 8292.
Aldehydes, Botanical chemistry