Question

1. Draw the product(s) of the following reactions HeCrO4 1. CH,COCVAICI 2. Zn (Hg)HCI 3. NBS (light) 1. KMnO4/H2SO4 og er CH3 NaNH2 NH3(0) 2. Show how you would synthesize the following compounds from toluene. OH O он Br

Answer 1

i) The benzylic carbon is converted into carboxylic acid with H, Cro. The reaction is as follows CH3 COOH H, Cro on sq CH3 COOH 1. CH.COCI/AICI CH, 2. Zn(Hg)/HCI CH3 NBS Y CH3 (Friedel Craft (reduction) (light) acylation) bromination at benzylic position iii) The benzylic carbon is converted into carboxylic acid with KMnO/H2SO4. The reaction is as follows brominalios da benzyic COOH 1. KMnO/H.SO COOH iv) The 2-chlorotoluene reacts with sodamine in liquid ammonia and forms benzyne which is coverted into ortho amino tolune and meta amino toluene. The reaction is as follows CH3 CH3 NaNH, NH2 CH3 CH3 CI NH, CD -NH₂