Q8(a)(ii). Chemical shifts of Hᵃ and Hᵇ
Compare the chemical shifts of the labelled protons Ha and Hb in the ¹H NMR spectrum of the following compounds D and E and justify your answer. [structures of methyl vinyl ether (D) and methyl vinyl ketone (E) given in the paper]
Answer in brief
Hb (enone E) absorbs about 2 ppm downfield of Ha (enol ether D).
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Coverschemical shiftshieldingmesomeric effectenol ethermethyl vinyl ketone
All parts of Question 8
- 8(a)(i) Coupling constants of the lettered protons5 marks
- 8(a)(ii) Chemical shifts of Hᵃ and Hᵇ5 marks
- 8(a)(iii) Number of ¹H NMR signals5 marks
- 8(b)(i) Structure of the halogenated ester10 marks
- 8(b)(ii) C₆H₁₂ alkenes with peaks at m/z 42 and 565 marks
- 8(c)(i) Characteristic fragment ions10 marks
- 8(c)(ii) Structure of C₄H₅NO₂10 marks