Q4(c)(ii). 1,2 versus 1,4 addition
Choose reagents converting methyl vinyl ketone to (1) the tertiary allylic alcohol shown and (2) pentan-2-one. [structure of the allylic alcohol given in the paper]
Answer in brief
(1) MeMgBr or MeLi, then aqueous work-up; (2) Me₂CuLi, then aqueous work-up.
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Covers1,2 vs 1,4 additionGilman reagent Me₂CuLiGrignard reagentconjugate additionmethyl vinyl ketone
All parts of Question 4
- 4(a) Primary kinetic isotope effect10 marks
- 4(b) Nucleophilic aromatic substitution10 marks
- 4(c)(i) Acidity and aromatic conjugate bases5 marks
- 4(c)(ii) 1,2 versus 1,4 addition5 marks
- 4(d) Pyrrole with chloroform and base10 marks