The signal for the acid proton of the product shows at d=~11.5 ppm in CDCI3 while it is found at d=~ ppm in DMSO-d6. What would be the best explanation for that? The acid proton forms a hydrogen bond with the chlorine atom of CDCI3 which leads more deshielding. The acid proton forms a hydrogen bond with the chlorine atom of CDCI3 which leads more shielding. The acid proton forms a hydrogen bond with the oxygen atom of DMSO-do which leads more shielding. The acid proton forms a hydrogen bond with the oxygen atom of DMSO-do which leads more deshielding.

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The signal for the acid proton of the product shows at d=-11.5 ppm in CDCl3 while it is found at d=-12.5 ppm in DMSO-d6. what would be the best explanation for that?

Williamson Ether Synthesis

The signal for the acid proton of the product shows at d=~11.5 ppm in CDCI3 while it is found at d=~12.5
ppm in DMSO-d6. What would be the best explanation for that?
The acid proton forms a hydrogen bond with the chlorine atom of CDCI3 which leads more deshielding.
The acid proton forms a hydrogen bond with the chlorine atom of CDCI3 which leads more shielding.
The acid proton forms a hydrogen bond with the oxygen atom of DMSO-d6 which leads more shielding.
The acid proton forms a hydrogen bond with the oxygen atom of DMSO-d6 which leads more deshielding.
DMSO-d6 is a more polar solvent than CDCI3.
Transcribed Image Text:The signal for the acid proton of the product shows at d=~11.5 ppm in CDCI3 while it is found at d=~12.5 ppm in DMSO-d6. What would be the best explanation for that? The acid proton forms a hydrogen bond with the chlorine atom of CDCI3 which leads more deshielding. The acid proton forms a hydrogen bond with the chlorine atom of CDCI3 which leads more shielding. The acid proton forms a hydrogen bond with the oxygen atom of DMSO-d6 which leads more shielding. The acid proton forms a hydrogen bond with the oxygen atom of DMSO-d6 which leads more deshielding. DMSO-d6 is a more polar solvent than CDCI3.
Expert Solution
Step 1

Given is that,  acidic proton gives ~11.5 ppm in CDCl3 and ~12.5 in DMSO.

That is signal using DMSO is deshielded than CDCl3.

 

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