eg CH BrO MW = 152 QUESTION: DETERMINE THE STRUCTURE ...

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eg CH BrO MW = 152 QUESTION: DETERMINE THE STRUCTURE ...

e.g. C 3 H 5 BrO 2 MW = 152QUESTION: DETERMINE THE STRUCTURESPECTRA AVAILABLE:• IR• 500 MHz 1 H NMR• 125 MHz 13 C NMR• MASS SPECSee : www.gh.wits.ac.za/chemnotes for this e.g.


FIRSTLY, WORK OUT THE DEGREE OF UNSATURATION:[theoretical maximum no. H – (actual H + Hal – N)]2IN THIS CASE, DU =1∴ STRUCTURE CAN CONTAIN EITHER 1 × DOUBLE BONDOR 1 × RINGIN THIS e.g. A RING IS UNLIKELY SINCE ONLY 3 × C ATOMS∴ MOST LIKELY CANDIDATES:OR


IR SPECTRUMOHC=O


13 C SPECTRUMCDCl 3CH 2CH 2C


1 H SPECTRUMOHCDCl 3CH 2 CH 2


MASS SPECTRUM= 152 - BrBrC 2 H 4BrC 3 H 4 OBr : 2 ISOTOPES, 79 Br & 81 Br


PROPOSE A STRUCTURE& VERIFY THAT IT IS COMPATIBLE WITH ALL THESPECTRA!

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