Question

Propose a structure for a compound with molecular formula C8H14O3 that fits the following spectroschopic data: HNMR: 1.0 (triplet, I=6), 1.6 (sextet, I=4), 2.2 (triplet, I=4)

Answer 1

Solution :-

Given formula = C8H14O3

Hydrocarbon with 8 carbons will have (8*2)+2 = 18 hydrogens

So the number of hydrogen deficient = 18 – 14 = 4

Number of unsaturation = 4/2 = 2

In the HNMR data we only have 3 peaks

l = 6 +4+4 = 14

so

1.0 triplet l=6 means 6 hydrogens gives the triplet so they are 2 CH3 groups which are attached to CH2

1.6 sextet is the CH2 groups which are having 5 adjacent hydrogens

2.2 ppm is the triplet means the CH2 group which is having 2 adjacent hydrogens

So the following is the possible structure for the given formula