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lect_13 - LECTURE 13(1 SIGNIFICANCE OF J MAGNITUDES(2...

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LECTURE 13 (1) SIGNIFICANCE OF J - MAGNITUDES (2) CORRELATING J VALUES WITH STRUCTURES WHY 4 PKS? WHY 3 PKS? J 5.5 5.5 J 9.5 5.5
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DISCUSS THE STRUCTURE OF C 20 H 18 O 6 1 H NMR (600 MHz CDCl 3 ): 8.28 d = 8.1, 1H 7.97 d = 8.1, 1H 7.81 s, 1H 5.15 d = 4.6, 1H 4.34 d = 6, 1H 3.86 – 3.80 m, 1H 3.74 s, 3H 3.73-3.67 m, 1H 3.64 dd = 6.2, 4.6, 1H 3.41 bs, 1H 2.89 bs, 1H 2.75 ddd = 8.6, 4.3, 2.7, 2H 1.73 s, 3H J CH : 8.28 – 173.5 7.97 – 206.7 7.81 – 173.5 nOe: 3.41 – 2.81 OH O H 3 C HO O O CH 3 O 1 4 1 5 6 7 20 12 14 17 10
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DISCUSS THE STRUCTURE OF C 20 H 18 O 6 1 H NMR (600 MHz CDCl 3 ): 8.28 d = 8.1, 1H 7.97 d = 8.1, 1H 7.81 s, 1H 5.15 d = 4.6, 1H 4.34 d = 6, 1H 3.86 – 3.80 m, 1H 3.74 s, 3H 3.73-3.67 m, 1H 3.64 dd = 6.2, 4.6, 1H 3.41 bs, 1H 2.89 bs, 1H 2.75 ddd = 8.6, 4.3, 2.7, 2H 1.73 s, 3H J CH : 8.26 – 173.5 7.97 – 206.7 7.81 – 173.5 nOe: 3.41 – 2.81 OH O H 3 C HO O O CH 3 O 1 4 1 5 6 7 20 12 14 17 10 4 9 1 20 O 8 12 OH O H 3 C HO 7 O CH 3 15 5 O 2
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DISCUSS THE EXPECTED 1 H NMR OF: 1. SPIN SYSTEMS 2. N+1, etc BEHAVIOR 3. RELATIVE CHEMICAL SHIFTS 4. COUPLING CONSTANT VALUES O 2 N O O O Cl Hb Ha Hb Ha Ha Hx Ha' Hx'
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Figure 4.11a pinanediol
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P133
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NOTES: H2 expect dd H6 expect dd or t H3/3’ expect ddd (note H2) H4 expect dd H5/5’ expect ddd Why 4 peaks Why 16 pks?
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