Question of 135
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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Start your 14-day free trial to unlock the full solution →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.
- 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.
- 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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