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Question of 135

Q.Write the names of reagent and equation for the preparation of the following Ether by Williamson's synthesis.

(i) 1 - propoxy propane
(ii) Ethoxy benzene
(iii) 2-Methoxy-2-Methyl propane
(iv) 1-Methoxy ethane
Gujarat GsebGSEB Higher Secondary Certificate (HSC) Examination 2025Subjective· 4mImportance★★★★★
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Williamson's synthesis reacts a sodium alkoxide/phenoxide (nucleophile) with a primary alkyl halide (SN2 electrophile) to form the ether; when one side is bulky/tertiary, that side must be used as the ALKOXIDE, not the halide, to avoid elimination.

General Williamson synthesis: R-O-Na + R'-X --> R-O-R' + NaX (an SN2 reaction; R'-X should be primary/unhindered, since a secondary/tertiary halide favours E2 elimination with the strongly basic alkoxide instead of substitution).

  1. 1-Propoxypropane, CH3CH2CH2-O-CH2CH2CH3 (a symmetrical ether): CH3CH2CH2-ONa (sodium propoxide) + CH3CH2CH2-Br (1-bromopropane) --> CH3CH2CH2-O-CH2CH2CH3 + NaBr
  2. Ethoxybenzene, C6H5-O-C2H5 (phenetole): C6H5-ONa (sodium phenoxide) + C2H5Br (bromoethane) --> C6H5-O-C2H5 + NaBr (Aryl halides cannot be used as the electrophile in Williamson synthesis - the C-X bond of an aryl halide resists SN2 - so the phenol must be the nucleophile/alkoxide side, and the alkyl halide the electrophile.)
  3. 2-Methoxy-2-methylpropane, (CH3)3C-O-CH3 (MTBE): …

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