Q.How will you prepare
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Start your 14-day free trial to unlock the full solution →Step 1. (i) Acetic anhydride from acetic acid: heat acetic acid with the dehydrating agent P2O5 (Section 12.12.C.5/12.14.3.1) -- 2 CH3COOH + P2O5 gives (CH3CO)2O + H2O.
Step 2. (ii) Ethyl acetate from methyl acetate: react methyl acetate with excess ethanol (H+ catalyst) -- transesterification (Section 12.14.4.3) exchanges the alcohol portion, giving ethyl acetate + methanol.
Step 3. (iii) Acetamide from methyl cyanide: treat methyl cyanide with cold concentrated HCl -- PARTIAL hydrolysis of the nitrile (Section 12.14.5.1, method 3) stops at the amide, CH3CONH2, rather than going on to the free acid.
Step 4. (iv) Lactic acid from ethanal: ethanal + HCN gives the cyanohydrin (lactonitrile), CH3CH(OH)CN (Section 12.5.A.1); acid hydrolysis of this nitrile then gives lactic acid, CH3CH(OH)COOH.
Step 5. (v) Acetophenone from acetyl chloride: react acetyl chloride with benzene in the presence of anhydrous AlCl3 -- Friedel-Crafts acylation (Section 12.3.D.2) -- giving acetophenone + HCl.
Step 6. (vi) Ethane from sodium acetate: electrolyse an aqueous solution of sodium acetate -- Kolbe's electrolytic decarboxylation (Section 12.12.C.3) -- 2 CH3COONa gives C2H6 (at the anode) + 2 CO2 + 2 Na.
Step 7. (vii) Benzoic acid from toluene: oxidise toluene with hot alkaline KMnO4, then acidify (Section 12.10.6) -- the entire methyl side chain is oxidised to -COOH, giving benzoic acid.
Step 8. (viii) Malachite green from benzaldehyde: condense benzaldehyde with two equivalents of N,N-dimethylaniline in the presence of concentrated H2SO4 (Section 12.5.F.7), giving the leuco base, which is then oxidised to the fully conjugated dye, malachite green.
Step 9. (ix) Cinnamic acid from benzaldehyde: condense benzaldehyde with malonic acid in the presence of pyridine (the Knoevenagel reaction, Section 12.5.F.5) -- the intermediate unsaturated diacid spontaneously decarboxylates to give cinnamic acid directly (Perkin's reaction, with acetic anhydride/sodium acetate, gives the identical product by a different route). …
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