Q5(d). Photodecarbonylation of diphenylcyclopropenone
Formulate the product(s) and give the mechanism for the following reaction:
[structure] → (hν)
Answer in brief
PhC≡CPh + ⁻:C≡O:⁺ diphenylacetylene and carbon monoxide, by photochemical decarbonylation through a biradical (or concerted cheletropic loss of CO).
With any Mains test series
Read the key points and the full model answer with a Mains test series
Every Mains test series (Civil Services, IFoS or Geo-Scientist) opens the solved IFoS Mains PYQ answers, the notes, the handbook and the daily answer archive until your Mains. The first test of each series is free. Civil Services and Geo-Scientist Mains PYQ solutions and Geo-Scientist Prelims PYQ solutions are free for everyone.
The full model answer
As written for the answer booklet: the diagram carries the working, the lines stay short. Read here only; it is not offered as a download.
Coverscarbon monoxidediphenylacetylenephotodecarbonylationn→π* excited statering strain
All parts of Question 5
- 5(a) Monomers of Teflon and Bakelite; addition or condensation5 marks
- 5(b) Products of complete hydrolysis of DNA5 marks
- 5(c) 3-Methylindene: OsO₄, HIO₄, then base5 marks
- 5(d) Photodecarbonylation of diphenylcyclopropenone5 marks
- 5(e) Chemical shift at 60 MHz and 100 MHz5 marks
- 5(f) λmax of CH₃Cl, CH₃Br, CH₃I: n→σ*5 marks
- 5(g) Bathochromic shift with increasing conjugation5 marks
- 5(h) McLafferty rearrangement: butyrophenone, m/z 120 and 1055 marks