1: 1.) 33percent NaNO2/H2O, conc. HCl, ethyl acrylate, 2.) Cu2O / 1.) acetone, ice cooling, 2.) 40 deg C, 2 h 2: 29.1 g / 25percent NaOH/H2O / methanol 4: 360 mg / 20percent HCl / 4 h / Ambient temperature 5: 220 mg / BBr3 / CH2Cl2 / 0.33 h / Ambient temperature 6: 200 mg / NaN3 / dimethylsulfoxide; H2O / 3 h / 90 °C 7: 1.) H2, 2.) HCl/Et2O / 1.) 10percent Pd/C / 1.) ethanol, 1 atm, r.t. View Scheme

hydrogen; palladium on activated charcoal in methanol; benzene

1: 72 percent / NaH / dimethylsulfoxide / 3 h / 60 °C 2: H2 / 10percent Pd/C / benzene; ethanol / 760 Torr / Ambient temperature View Scheme

1: 72 percent / NaH / dimethylsulfoxide / 3 h / 60 °C 2: H2 / 10percent Pd/C / benzene; ethanol / 760 Torr / Ambient temperature View Scheme

1: 1.) 47percent HBr, NaNO2, 2.) Cu2O / 1.) acetone, H2O, 5 deg C, 20 min, 2.) acetone, H2O, 35 deg C 2: 51.7 percent / 1 h / 120 °C 3: 82 percent / 2N HCl / ethanol / 15 h / Heating View Scheme

hydrogenchloride; sodium nitrite in water; acetone

copper(I) oxide; hydrogenchloride; water; ethyl acrylate; sodium nitrite 1.) acetone, ice cooling, 2.) 40 deg C, 2 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

copper(I) oxide; hydrogenchloride; water; sodium nitrite 1.) acetone, ice cooling, 2.) 40 deg C, 2 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

(i) NaNO2, aq. HCl, acetone, (ii) /BRN= 773866/, Cu2O; Multistep reaction;