COSY and DEPT - Two CH 2 overlapping Chapter 6 Problems ‐...

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COSY and DEPT 2D NMR and Spectral Edi8ng
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COSY (Correla8on Spectroscopy) Proton‐proton correla8on through J coupling Use two 90‐degree pulses, ( π /2)x – t1‐ ( π /2)x – Acquire FID Fourier Transform 2‐dimensional NMR
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Magne8za8on Changes in COSY Experiment FID
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COSY of CHCl 3 A collec8on of FIDs FT FT t 2 t 1
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COSY of Methyl Acetate 1D 1 H-NMR COSY
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COSY of b‐Chloroacrylic acid Stacked plot Contour plot
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Typical COSYs are Recorded in Lower Digital Resolu8on
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Predicted COSY for 1‐Nitropropane Diagonal peaks Cross peaks a b c a b c
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Ethyl Benzene
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Annulene
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Citronellol Diastereotopic H2s Diastereotopic H4s Allylic coupling
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HETCOR ‐ 1 H‐ 13 C Correla8on 1 H 13 C
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HETCOR ‐ 2‐Nitropropane 2 2 1 1
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HETCOR ‐ Isopentyl Acetate
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DEPT ( D istor8onless E nhancement by P olariza8on T ransfer) 13 C-signal intensity DEPT45 DEPT90 DEPT135 DEPT sequence is designed to enhance 13 C signal, depending on the number of protons attached.
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Typical DEPT Experiment
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DEPT ‐ Lactam CH 3 CH 2 CH C=O A peak is hidden
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Chapter 6 Problems ‐ 6.1(a)
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Chapter 6 Problems ‐ 6.1(a) (IHD = 4) -CH 3 CH 2 CH 2
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Chapter 6 Problems ‐ 6.1(a) -CH 2 -CH 2 -CH 2 -CH 2 -CH 3
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Unformatted text preview: Two CH 2 overlapping Chapter 6 Problems ‐ 6.1(c) Chapter 6 Problems ‐ 6.1(c) (IHD = 1) No aromatic Or alkene protons 1H 2H 6H Chapter 6 Problems ‐ 6.1(c) Only 3 carbon peaks No sp2 carbon A ring with symmetry Chapter 6 Problems ‐ 6.1(c) Cl H H diastereotopic protons enantiotopic carbons Chapter 6 Problems ‐ 6.1(d) Chapter 6 Problems ‐ 6.1(d) (IHD = 4) 2H, two OH groups 3H Trisubstituted benzene 3H, CH 3-Ar Chapter 6 Problems ‐ 6.1(d) DEPT90 DEPT135 3 CH carbons + 3 C carbons - no symmetry-CH 3 Chapter 6 Problems ‐ 6.1(d) OH OH H 3 C Need expanded 1 H-NMR! Chapter 6 Problems ‐ 6.1(e) Chapter 6 Problems ‐ 6.1(e) (IHD = 2) 3 alkene protons 1H 2H 1H 1H 1H 2H 2H Chapter 6 Problems ‐ 6.1(e) DEPT90 DEPT135 CH CH CH2 CH2 CH2 CH2 Chapter 6 Problems ‐ 6.1(e) H H H Allylic coupling to CH2 H H H CH 2 Diastereotopic CH2 Chapter 6 Problems ‐ 6.1(e) H H H CH 2 H 2 C CH Chapter 6 Problems ‐ 6.1(e) H H H CH 2 H 2 C CH H 2 C diastereotopic H H H CH 2 H 2 C CH H 2 C O...
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