Q7(e). State-dependent diene chemistry and photo-Fries rearrangement
(i) Give products associated with S₁ and T₁ excitation of buta-1,3-diene. (ii) Complete p-cresol —(PhCOCl, aq. NaOH)→ A —(hν)→ B.
Model answer
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Coversphoto-Fries rearrangementsinglet and triplet excitationbutadiene photochemistrycyclobuteneSchotten–Baumann benzoylation
All parts of Question 7
- 7(a)(i) A beta-chloroamine and sulfonyl chloride5 marks
- 7(a)(ii) Hydration followed by oxidation5 marks
- 7(b) Ireland–Claisen rearrangement of an allylic acetate10 marks
- 7(c)(i) Solvolysis of a tertiary allylic bromide5 marks
- 7(c)(ii) Ring expansion of vinylcyclobutane5 marks
- 7(d) Stability of triarylmethyl radicals5 marks
- 7(e) State-dependent diene chemistry and photo-Fries rearrangement5 marks