Unit 30: Spectroscopy-2 NMR — Long Questions

Q3.b.Predict the ¹H NMR spectrum of 1-butanoic acid (CH₃CH₂CH₂COOH).

Q3.c.An organic compound has a molecular formula C₂H₅Cl. [The ¹H NMR spectrum referenced in the textbook alongside this question was not legible/reproduced in the supplied page images.] Deduce the structure of the compound by using its spectrum. Explain your working in detail.

Q3.d.An organic compound has a formula C₄H₈O. In laboratory, the compound gives 2,4-DNPH and iodoform tests positive but Fehling's test shows a negative result. [The ¹H NMR spectrum referenced in the textbook alongside this question was not legible/reproduced in the supplied page images.] Deduce the structure of the compound and justify your answer.