Discussion
An organic compound with molecular formula C4H10O shows the following spectral data in 1H-NMR is δ : 0.9(t, J = 6 Hz, 3H) 1.1 (d, J = 6.5 Hz, 3H), 1.5 - 1.6(m, 2H), 3.6 (broad singlet, 1H, Ex. D2O), 3.9 (Sextet, J = 6.5 Hz, 1H). The correct structure of the compound is :
Answer: C
The compound is CH3-CH2-CH(CH3)-OH, butan-2-ol.
Read the spectrum: the triplet at 0.9 (3H) is a CH3 next to a CH2; the doublet at 1.1 (3H) is a CH3 next to a single CH; the multiplet at 1.5-1.6 (2H) is the CH2; the broad singlet at 3.6 (1H) exchanges with D2O, so it is the OH; and the sextet at 3.9 (1H) is a CH-O proton coupled to five neighbouring protons (CH3 plus CH2).
Only butan-2-ol has a CH3CH2 group, a CH3CH group and a CH(OH) proton with five neighbours. 2-Methylpropan-1-ol would show a six-proton doublet, butan-1-ol no methyl doublet, and tert-butyl alcohol a single nine-proton singlet.
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