Q8(c)(ii). Structure from an aldol-condensation spectrum
Identify the benzaldehyde/acetone base-condensation product with ¹H NMR δ 2.31 (s, 3H), 6.73 (d, 1H, J = 16 Hz), 7.32–7.40 (m, 5H), 7.52 (d, 1H, J = 16 Hz).
Answer in brief
The product is (E)-4-phenylbut-3-en-2-one, benzylideneacetone: PhCH=CHCOCH₃.
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CoversbenzylideneacetoneClaisen-Schmidt condensationtrans coupling constant 16 Hzproton NMR structure elucidationaldol condensation
All parts of Question 8
- 8(a)(i) Axial versus equatorial alpha chlorine5 marks
- 8(a)(ii) IR-active vibrations5 marks
- 8(b) Mass spectra of benzyl alcohol and anisole10 marks
- 8(c)(i) NMR distinction of two isomer pairs10 marks
- 8(c)(ii) Structure from an aldol-condensation spectrum10 marks