Question

6). (10 points) Predict the mononitration products of the following compounds. a) o-nitrotoluene b) m-chlorotoluene c) o-bromobenzoic acid d) p-methoxybenzoic acid e) m-cresol (m-methylphenol) (Two products) (Three products) (Two products) (One product) (Three products) 7). (12 points) Show how you would synthesize the following aromatic derivatives from benzene. You don't have to show mechanisms just show synthesis pathways. a) p-tert-butylnitrobenzene b) p-toluenesulfonic acid c) p-chlorotoluene glad noeg banorte

Answer 1

CH Ha 504. o-nitrotolume (tonomnad - Hy as Osthoand- para doreeting, whereas - No, ir nuta directing. In the first product no entes para to - CH, and muta to. - No, In the second product -NO, anters. ortho to - CH₃ and mata to No. Oridy ist. one is formed.. ен, (0) B H MOs+ , E 10- + + -ce H₂SO4 m-chlasotoluene CH3 Moa (fornud). сH, | 아, La ay be - CH₃ and - el both are ortho and para directing so. the three products, while obtained accordingly, but due to steric reason. only. (HE M O2) is formed

COOH Br HNO3 + H₂SO4. COOH Br. HNO3 + H2564, ET EL MOL QM (formad) COOH Bn. + EU o-bromo benzoic acid -000H as meta directing, -Br is ortho and para dereeting. In the first product. Ho, enters meta to cook and ortho to Br. In the second product. - NO₂ enters meta to - cooh and para to Br. Only second product is formed. OME NOL d) - Me MO ом Bu HNO3 + H2SO4 B COOH COOH p-methoxy benzoic acid -ome is ortho and para directing, cook is nuta. available for - No, déricting. So, only one position is to enter, ortho to -ome and para mutato .cooh. - Me Me No 1 Elon HNO3 + Hasoy, BMO + B ont m-esesol C (formed) . -CHis ortho and para directing, -OH is also ortho and pasa directing. In the first product. -HO, enters ortho to both -CH and -Oh, In the second product - No enters para to -CH₂ and ortho to -oh. In the third product -No enters ortho to - CH₃ and pasa to -OH. Only second one (me HOL) is formed OH тон NO HNO, Hg504 NO - p-tert-butyl nitrobenzene tert-butyl benzene is electron donating, so os tho and para derecting. Since - test butyl is bulky group. so nitration occurs at passa para position to. give p-test-butylnitrobenzene as major product.

CHU Anky. As SOH p-tolecane sulfonic acid CH CH₃ Cl. an 5 El . & anhy. Allh Felh major. p-chloro toluene