Question

Q 2(a) [60 Marks] Provide Products 1-3 for the first three reaction sequences, and give Reagents 1-3 for the final reaction sequence. Make sure to include your rough work (intermediates can be shown, but mechanisms not required) to show how you arrived at answers in each case. 1. NaNO2, HCI, 0 °C Product 1 HNY 2. HBF4 Br OCH3 NEN Product 2 1. Cl2, FeCl2 2. HNO3, H2SO4, heat Product 3 3. NaOCH3, heat 4. Sn, HCI 5. NaNO2, HCI, 0 °C 6. CuBr OH Reagents 1 Reagents 2 Reagents 3 PhH

Answer 1

Q-2 (a) HBFG NaNo, + Hrd - Hal 0-5°C -87_. . HNT HT BY (o-Bromo. ( Aniline (o-Bromo Benzene- diazonium - chloride -N2₂ - BF 4 ) - By- 1- Bromo 2-Fluro Benzene C o -Bromo Aniline Hal at o 5°c and diazonium chloride producedo -Bromo and Than heated React with sodiury nitrite and produced o- Bromo Benzene- Then React with HBF4 and Benzene diazonium fluro Borate gives - Boomo 2-fluro Benzene -octa OCH3 OCH3 NON ! NENO LOI NENKY CH3 P methyl Anisole Benzene diazonium chloride (Diazo dye) s p -methyl anisole React with Benzene diar - chloride and produced diazo dye.

HNO H2SO4 heat Benzene NO2 chloro- Benzene Hochlorot 4- Nitro 3 enzeтe A ochy NaocHz nect sn, Hed Reduction -Nach NO P-nitro Anisole INaNo Hel LOCH, LOCHA Cu-B8 A - N2,-euce 20 BY P-methoxy Benzene diazoninen chloride (P-Bromo Anisole

CH, CH J Mg Br 7- [o] . Рcc weak oxidant Benzaldehyde (Benzy \ - Alcohol -oms 87 tell, CH₂ Рcc г. strong КММ Weak or oxidant ( Ethye Phenyl ketone OR CH₂ CH₂ mg Br COD_ PCC weak oxidant Hito ---PCE OR kmnoul Ph hered Benzaldehyde and 1 Benzyl Alcohol React with weak oxidant pyridinium- chloro chromate CPCC) and produced Benzaldeh then react grignard reagent (CH₂ CH₂ mg Br, Hato) and then once again oxidation and produced ethre. methyl ketone, GRAPETOWY