Question

draw a mechanism for methyl 3 benzoate

2. For the nitration of methyl benzoate: Which product did you get? What evidence doyou have for this? Wasyourproduct pure? Whatevidence do you have for this? Explain your a. b. evidence. c. Draw the mechanism for the product you got. d. Calculate percent yield. Show your work

Answer 1

Nitration of Methyl Benzoate -> The nitration of methyl benzoale to prepare methy) m-nitrobenzoate is an example of electrophelie aromatie substitution reactions, 90) which a hydrogen atom of aromatie ring as sreplaced by a nitro group. - This Yeaction as carried out with a mixture of concentrated sulfuric acid reacts with nitric acid. reaction l H2SO4 l NO2 HNO3 → The Carbo methoxy group (Meta directing group) directs the aromatic substitution preferably to those positions that are meta to pt. → meta product is the principle product , impurities will include that small amounts of ortho & para isomers., dinitration product ave vory poor quantities [negligible con removed when desired Product is washed with methond & purified by recrystallization ] Mechanism E step o : formation of Hinog ta tip 504 - NO, + 430®+ 24.5.

step o formation of s-complexe QLO-CH3 Rate Determing step 7 (slow) + NO =2=0 O 2- O o=2+ 6- complexe. step @ Falmation of product соос+3 COOCH3... VANO +20 calculation of % of yield Melting point of m-nitro benzoate 78-80°C Mass of the methyl benzoate = 3-05009 mass product = 39.22259 mass filter paper = 0.69639 mass final product = 2.6996 g C645 CO, Ctz + H₂. Noz Coty CO2 CH3 NO2 + Heo bell-off molar mass of C H5 COCH3 = 136.1487 mass of C H5CO, CH3 = 3.05009

Number of mole = 3:0500 , 0.022 mol 136.1487 1 mol of C6H5CO2 CH3 needed to produce Of Chei CO2 CH3 NO2 i moli needed to produce 0.022 mol of Chi CO₂ CH3 needed to produce o mol of CH4CO₂ CH 3 NO2 molar mass of cotti co, CH3ND, = 181:1463 The Theoreticay yield of product = 0.022 mol x 181 =1463 Troll : 3.98529 Actual yield = 38.52629 % of yield of product = 206996.9 x 100% 3.98529 = 67.741