An organic reaction used to convert an aryl diazonium salt into an aryl halide using a copper(I) halide catalyst is called:
- (a)Sandmeyer reaction
- (b)Balz-Schiemann reaction
- (c)Finkelstein reaction
- (d)Gattermann reaction
Answer
Why
Correct — A. The Sandmeyer reaction is the one defined by the catalyst the question names: an aryl diazonium salt treated with a copper(I) halide in the matching acid, with nitrogen leaving as gas.
ArN₂⁺Cl⁻ + CuCl → ArCl + N₂
ArN₂⁺Br⁻ + CuBr → ArBr + N₂
The same route with CuCN puts a cyanide group on the ring, which is why Sandmeyer is taught as the general way of replacing the −N₂⁺ group left behind by an amine. That is option (a).
Why the others are wrong
- (b)Balz-Schiemann reaction — The Balz-Schiemann reaction makes an aryl fluoride, by isolating the diazonium tetrafluoroborate and heating it. No copper is involved anywhere in it.
- (c)Finkelstein reaction — The Finkelstein reaction is a halide exchange on an alkyl halide, using NaI in dry acetone to give the iodide. It begins from no diazonium salt at all.
- (d)Gattermann reaction — The Gattermann reaction reaches the same aryl halide but with copper powder and HX in place of the copper(I) salt. The question specifies a copper(I) halide, which names Sandmeyer.
Concept
Diazonium chemistry is the classroom route from aniline to almost any substituted benzene.
Aniline with NaNO₂ and HCl at 0-5 °C gives benzenediazonium chloride. That step is diazotisation, and the low temperature matters because the salt decomposes on warming.
The −N₂⁺ group is then swapped for Cl, Br, CN, I, F or OH, and each swap carries its own name. Learn which reagent goes with which name, because SSC asks the name from the reagent.
Gattermann is a name attached to more than one reaction in textbooks, including an aldehyde synthesis. Here the intended contrast is the diazonium variant, which differs from Sandmeyer only in using copper powder instead of a copper(I) salt.
Key facts
- The Sandmeyer reaction converts an aryl diazonium salt into an aryl chloride, bromide or cyanide using CuCl, CuBr or CuCN.
- Benzenediazonium chloride is prepared from aniline with NaNO2 and HCl at 0-5 °C.
- The Balz-Schiemann reaction gives an aryl fluoride by heating the diazonium tetrafluoroborate.
- The Finkelstein reaction exchanges halogen on an alkyl halide using NaI in dry acetone.
Study next
Common traps
- Choosing Gattermann because it also yields an aryl halide, when the question names a copper(I) halide catalyst.
- Choosing Finkelstein on the word halide alone, when it acts on alkyl halides and needs no diazonium salt.
SSC asks named reagents and named reactions as straight recall, without a mechanism. The Grignard reagent from haloalkanes and magnesium is asked on 11 Sep 2024, 12:30, General Awareness Q.8.
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