Can Someone Help Me with Benzoic Acid & Benzaldehyde?

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SUMMARY

The discussion focuses on the effects of substituents on the acidity of benzoic acid and the use of HNMR to distinguish between ortho, meta, and para-ethyl benzaldehyde. It is established that electron-donating groups decrease the acidity of benzoic acid due to resonance effects, particularly in ortho and para positions, while meta positions only exhibit inductive effects. HNMR can effectively differentiate these isomers, revealing distinct proton environments and integration ratios. The ortho-ethylbenzaldehyde shows a unique splitting pattern due to its remaining ortho proton, while para-substitution results in a simplified spectrum with symmetry.

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  • Understanding of benzoic acid acidity and substituent effects
  • Knowledge of resonance and inductive effects in organic chemistry
  • Familiarity with HNMR spectroscopy principles
  • Ability to interpret NMR spectra and integration ratios
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  • Study the resonance and inductive effects of substituents on aromatic compounds
  • Learn about HNMR spectroscopy and its applications in organic chemistry
  • Explore the differences in NMR spectra for ortho, meta, and para substituted compounds
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Can someone please help me...

I have a few questions to ask.. if someone can help I will very thankfull..
1st: Can someone explain to me the para, ortho, and meta effects of subsituents on the acidity of benzoic acid..
2nd: Can HNMR be used to distinguish ortho-ethyl benzaldehyde, meta-ethyl benzaldehyde, and para-ethyl benzaldehde..
 
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If the group is an electron donating group (+R/+I), then the acidity of benzoic acid decreases. Opposite when an ewg is present (-R/-I).

In the ortho and para position, the groups can partake in resonance, and the resonance effect is greater than the inductive effect. Hence, the +R/-R groups effect the acidity more than the +I/-I groups. If a group is present on the ortho position, and it can form H-bonds, it will do so with th -COOH group present.

In the meta position, the groups do not undergo resonance with the benzene ring and can only show their +I/-I effect.
 
samadiqbal said:
I have a few questions to ask.. if someone can help I will very thankfull..
1st: Can someone explain to me the para, ortho, and meta effects of subsituents on the acidity of benzoic acid..
2nd: Can HNMR be used to distinguish ortho-ethyl benzaldehyde, meta-ethyl benzaldehyde, and para-ethyl benzaldehde..

Yes, NMR can be used to determine the differences between ortho, meta and para substitution. You can see that there will be one ortho proton remaining for ortho-ethylbenzaldehyde. This proton will be split by the others in the benzene ring but should be far enough from the others to be completely resolved. Integtration will give a 1:4 ratio with the other aromatic protons. Para-substitution will yield only two unique aromatic protons by introducing a C2 symmetry element. Both ortho protons will be identical (no ortho-ortho coupling) and both meta protons will be identical (no meta-meta coupling). The result is a pair of resolved doublets that integrate 1:1. You can see the spectra for yourself at the following site:

http://www.Newton.dep.anl.gov/askasci/chem00/chem00800.htm
 

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