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Which molecule cyclohexanecarbaldehyde or benzaldehyde, would you expect the stretching band of the carbonyl to appear...

Which molecule cyclohexanecarbaldehyde or benzaldehyde, would you expect the stretching band of the carbonyl to appear at a higher frequency? Explain.

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Answer #1

C-O stretching frequency depends on strength of the bond.

In case of cyclohexanecarbaldehyde and benzaldehyde, one molecule contain conjugated aldehyde while the other contain non conjugated aldehyde group.

due to conjugation in the molecule, C=O bond becomes weaker compared to cyclohexanecarbaldehyde .

Therefore, C=O stretching frequency is observed in conjugated aldehyde is 10-40 cm-1 less than that of non conjugated aldehydes.

cyclohexanecarbaldehyde C=O stretching frequency = 1705 cm-1

benzaldehyde C=O stretching frequency = 1690cm-1

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