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H-NMR Spectral Correlations

Diene 10

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A)  These Hydrogens have no three-bond neighbors and no coupling, so they show up as a singlet.  They are relatively upfield because they are not directly attached to the alkene double bonds. 
B)  Hydrogen B couples with Hydrogen C, so the splitting pattern is not a singlet.  Hydrogen B is relatively downfield because of the alkene, which is electron rich and deshields Hydrogen B. 
C)  Hydrogen C couples with Hydrogen B, so the splitting pattern is not a singlet.  Hydrogen C, like Hydrogen B, is relatively downfield due to the alkene, which is electron rich and deshields hydrogen C.
D)  Hydrogen D has no three-bond neighbors nor does it exhibit any long range couplings, so it shows up as a singlet.  Its chemical shift is similar to Hydrogen A; both are upfield because they are not directly attached to the electron rich alkene bond.  Hydrogen D is more upfield than Hydrogen E because it is trans to the electronegative Bromine atom.
E)  Hydrogen E also has no three-bond neighbors and does not exhibit coupling; therefore, it shows up as a singlet.  It is slightly more downfield than Hydrogen D because it is cis to the electronegative Bromine atom.

 

Dienone 11

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A)  Hydrogen A is the only Hydrogen in this molecule that has no Hydrogen bond neighbors, so it shows up as a singlet.  It is relatively downfield because it is directly attached to the electron-rich alkene.
B)  Hydrogen B has multiple Hydrogen-neighbors; therefore, it shows up as a multiplet.  It is relatively upfield because it is not directly attached to an alkene.
C)  Hydrogen C also shows up as a multiplet, and is higher upfield than Hydrogen B because it is further away from the alkene and ketone bond.s
D)  Hydrogen D has a higher coupling constant than Hydrogen E because it is trans to Hydrogen F, therefore, its coupling constant is higher than that of hydrogen E.  
E)  Hydrogen E has a lower coupling constant than Hydrogen D because it couples with hydrogen F, to which it is cis.
F)  Hydrogen F couples with both Hydrogen D and E and therefore has two coupling constants and shows up as a doublet of doublets.  F is the most downfield because it is directly attached to the alkene bonds and is close to the ring.

 

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