Q8(a)(i). Axial versus equatorial alpha chlorine
Distinguish the drawn α-chloro bicyclic ketones X and Y by IR; X has axial Cl and Y equatorial Cl. [structures given in the paper]
Answer in brief
Y normally has the higher carbonyl stretching frequency; axial-Cl X shows a smaller upward shift from the parent ketone.
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Coversα-haloketone ruleIR carbonyl frequencyaxial vs equatorial chlorinefield effectconformational analysis
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