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Q.(a) Give an example of a primary alcohol that reacts with Lucas reagent at room temperature.

(b) Why is ether stored in a coloured/dark bottle?
(c) Carry out the following conversions:
(i) Phenol → Picric acid
(ii) Phenol → Salicylic acid
Tripura TbseHigher Secondary (+2 Stage) Examination 2026Subjective· 4mImportance★★★★★
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Benzylic/allylic primary alcohols react fast with Lucas reagent despite being 'primary' because their carbocations are resonance-stabilised; ethers autoxidise to peroxides in light so are stored in dark bottles; phenol is converted to picric acid via sulphonation then nitration, and to salicylic acid via the Kolbe-Schmidt carboxylation.

  1. Ordinarily, primary alcohols react only very slowly with Lucas reagent (since the SN1 mechanism needs a reasonably stable carbocation, and primary carbocations are unstable). However, benzyl alcohol (C6H5CH2OH), though a primary alcohol, reacts at room temperature because the intermediate benzylic carbocation (C6H5CH2+) is strongly stabilised by resonance delocalisation into the aromatic ring, so the SN1 substitution proceeds readily even without heating.
  2. Diethyl ether and similar ethers, on prolonged exposure to air and light, slowly undergo autoxidation to form organic peroxides, which are unstable and highly explosive on concentration/heating/distillation. Storing ether in a coloured (amber/dark) bottle blocks light, which is a key requirement for this photochemical peroxide-forming reaction, thereby minimising peroxide build-up and the associated explosion hazard. (c)(i) Phenol -> Picric acid: Direct nitration of phenol with concentrated HNO3 is not practical (side oxidation reactions occur), so phenol is first sulphonated with concentrated H2SO4 to give phenol-2,4-disulphonic acid, and this is then treated with concentrated HNO3, which both nitrates the ring and displaces/hydrolyses the sulphonic acid groups, giving 2,4,6-trinitrophenol (picric acid). …

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