Identify structure and name of unknown, detailed explaination for both IR and NM

Question

Identify structure and name of unknown, detailed explaination for both IR and NMR. Also errors in these IR and NMR?

H2O NaOH HC1 H SO Halide Test Nitrogen Test Unsaturation Test Ignition Test (aromaticity) Acetyl chloride Cerium (V) test Lucas Test The two solutions were separate after Insoluble mixing The compound didn't dissolve in base Insoluble The compound didn't dissolve in acid Insoluble The compound wasn't soluble in Insoluble concentrated sulfuric acid No voluminous precipitate was Negative observed The clear solution was observed. No Negative dark blue color Negative After 3 drops of 2% solution of bromine in methylene chloride, the red color occurred Flame occurred Negativel Positive Evolution of heat and HCl gas Positive alcohol Immediate color change from yellow to orange Positive tertiary alcohol/ Cloudy solution observed after one allyl alcohol. minute

Explanation / Answer

The above qualitaitve tests are not in match with the given IR-NMR

If still we want to justify the results with the spectra

a) the test is not of alkene or alkyne or aromatic compounds

b) the test is negative for halogens and nitrogens

c) it is not soluble in acid or base either, so cannot be carboxylic acid

d) So, it could be aldehyde as i Can see the peak near 1700 (C=O)

e) however again the NMR peak of aldehyde near 9-10 ppm is not given

f) 2950

2946 : C-H stretching (sp3)

2820: C-H(sp2, stretching, aldehyde

1450 : CH3 stretch

1390: CH2, CH3 bend

1700 : C=O

so the possible compound is Butanal (CH3-CH2-CH2CHO)

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