Question

4. When 10 g of benzene (Molar mass 78 g/mol) reacts with 9 mL of concentrated HNO3 (16 M) and 9 mL of H2SO4 (18 M), 8.1 g of nitrobenzene (molar mass 123 g/mol) and 1.2 g of an unknown compound with a high boiling point are obtained. a. Identify the limiting reagent. b. Calculate the percent yield of nitrobenzene. c. Give the name and structure of the most probable side product with the high melting point. d. Explain, with the aid of a mechanism, the role of H2SO4 in the reaction. e. Supposing the crystalline compound (1.2 g) has the formula C&H4N204, calculate the yield of this side product. 5. The nitration of furan leads preferentially to 1- nitrofuran rather than the 2-nitrofuran isomer. Explain by considering carefully the stability of the o-complex leading to each isomer. NO2 NO2 NO2 Pyridine N-oxides can also react in electrophilic aromatic substitutions. In the reaction below, only a single product is obtained. Use resonance structures to justify the selective formation of this product. 6. NO2 HNO3 H2SO4 ON

Answer 1

NO 2 AIO ueno Com pound Now O mol u mo! 어 ßente h e Co.na Me!nJ L molert HNUsし0.N4undr)

yiele/ IS-72 る aie RDs n Nさ MAM kAo/ 어 나 Can be formed 0-128 mols

ed 2. 久1.5 ND No

A/C 2. A1O 0L NO