UPSC Civil Services (Mains), Chemistry optional · 2022 · Paper II
Q4(b)(ii). p-Nitrotoluene to m-nitrotoluene
Question
How will you convert p-nitrotoluene to m-nitrotoluene?
Answer in brief
Reduce NO₂ to NH₂, acetylate, nitrate ortho to NHAc (meta to CH₃), hydrolyse, then remove NH₂ through the diazonium salt with H₃PO₂.
Part of VKC Basic
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The full model answer
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Coversm-nitrotoluenediazonium saltH₃PO₂ deaminationdirecting groupacetanilide nitration
All parts of Question 4
- 4(a)(i) trans-But-2-ene with perbenzoic acid, then hydroxide10 marks
- 4(a)(ii) Loss of optical activity of an imine with sodium ethoxide5 marks
- 4(b)(i) Dibromocyclopentanes from cyclopentane and excess bromine10 marks
- 4(b)(ii) p-Nitrotoluene to m-nitrotoluene5 marks
- 4(c) Phenol to coumarin20 marks