475091-53-3

Upstream product

• 100-19-6 (4-nitrophenyl)ethanone 
• 318503-30-9 4-(4'-nitrophenyl)-4-hydroxypentan-2-one 

Downstream Products

• 475091-54-4 4-bromo-4-(4'-nitrophenyl)pentan-2-one 
• 318503-30-9 4-(4'-nitrophenyl)-4-hydroxypentan-2-one 

Relevant academic research and scientific papers

Competing base-promoted E2 and E1 reactions of an acidic tertiary substrate

The solvolysis of 4-chloro-4-(4′-nitrophenyl)pentan-2-one (1-Cl) in aqueous acetonitrile yields the alcohol 4-hydroxy-4-(4′-nitrophenyl)pentan-2-one (1-OH) and the elimination products 4-(4′-nitrophenyl)-2-oxopent-4-ene (2), (E)-4-(4′-nitrophenyl)-2-oxopent-3-ene (3), and (Z)-4-(4′-nitrophenyl)-2-oxopent-3-ene (4). Addition of thiocyanate ion does not increase the total reaction rate in 25 vol% acetonitrile in water, but gives rise to the substitution products 1-SCN and 1-NCS, at the expense of 1-OH, and a small increase in the fraction of alkene 3. Addition of acetate ion and other weak bases gives rise to base-promoted E2 (or E1cB) to give alkene 3 (and 4). The Bronsted parameter for this reaction was measured as β = 0.76. Water-promoted E2 (or E1cB) reaction was not observed.