Q7(b)(ii). Furil to furilic acid: benzilic acid rearrangement
Study the following chemical transformation and propose structure of A. Give the possible mechanism for the formation of the product in the reaction. [A, (i) NaOH (ii) H⁺ → product (furilic acid) given in the paper]
Answer in brief
A is furil, 1,2-di(furan-2-yl)ethane-1,2-dione. Hydroxide brings about the benzilic acid rearrangement; acid then gives furilic acid.
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Coversbenzilic acid rearrangementfurilfurilic acid1,2-diketone1,2-shift
All parts of Question 7
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- 7(a)(ii) 2-Naphthoic acid to a urethane: Curtius rearrangement5 marks
- 7(b)(i) 6π electrocyclic ring closure: thermal and photochemical modes5 marks
- 7(b)(ii) Furil to furilic acid: benzilic acid rearrangement5 marks
- 7(c)(i) 4-Methoxybenzaldehyde with NaCN: benzoin condensation5 marks
- 7(c)(ii) Norrish Type II against Type I in two ketones5 marks