Question:

The antifertility drug “Novestrol” can react with :

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Novestrol (ethynylestradiol type steroid) has a phenolic -OH ring, a tertiary alcohol and a C-C triple bond (no carbonyl).
Updated On: Nov 5, 2026
  • \(\mathrm{Br_2}\) /water; \(\mathrm{ZnCl_2}\) /HCl; \(\mathrm{FeCl_3}\)
  • \(\mathrm{Br_2}\) /water; \(\mathrm{ZnCl_2}\) /HCl; NaOCl
  • Alcoholic HCN; NaOCl; \(\mathrm{ZnCl_2}\) /HCl
  • \(\mathrm{ZnCl_2}\) /HCl; \(\mathrm{FeCl_3}\) ; Alcoholic HCN
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The Correct Option is A

Solution and Explanation

Novestrol (the antifertility drug, ethynylestradiol type) contains a phenolic ring bearing a free -OH, a tertiary alcohol group at C-17 and an ethynyl group; it has no C=O group.
1) Br2/water: reacts with the activated phenol ring (bromination).
2) ZnCl2/HCl (Lucas reagent): reacts with the tertiary alcohol to give a turbid chloride.
3) FeCl3: gives a coloured complex with the phenolic -OH.
NaOCl (haloform) needs a methyl ketone or CH3CH(OH)- group, and alcoholic HCN needs a carbonyl group; neither is present.
So only the set Br2/water, ZnCl2/HCl, FeCl3 works.
Answer: (1) Br2 /water; ZnCl2 /HCl; FeCl3
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