Question

The signals in the 1H NMR spectrum of butanoic acid are labelled from A to D....

The signals in the 1H NMR spectrum of butanoic acid are labelled from A to D. Considering the spectrum, answer the questions below:

  1. [4 marks] Complete the table:

Signal

Chemical shift, δ (ppm)

Splitting pattern

(singlet, doublet, triplet, quartet, pentet, sixtet, septet, octet, nonet, multiplet)

# of H neighbours

Integration             (# of protons)

Circle or highlight the proton(s) that give rise to this signal

A

11.60

CH3CH2CH2COOH

B

2.35

CH3CH2CH2COOH

C

1.68

CH3CH2CH2COOH

D

0.98

CH3CH2CH2COOH

  1. [2 marks] Compare this spectrum with the spectrum of 1-butanol. A carboxylic acid functional group contains two electronegative oxygen atoms, compared to one oxygen atom in an alcohol functional group. Given this, why is the highest non-OH proton peak in 1-butanol at a higher ppm value than the highest non-OH proton peak in butanoic acid?
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