Question

Propose a structure for a compound with molecular formula C₈H₁₅ClO₃ that fits the following spectroscopic data.
IR: 1780 cm^-1, 1150 cm^-1
1H NMR: 1.1δ (triplet, I=6), 1.9δ (quartet, I=2), 2.8δ (triplet, I=2), 3.4δ (quartet, I=4), 4.2δ (triplet, I=1)
¹³C NMR: 15, 31, 38, 57, 100, 173

Answer 1

Answer: Correct structure IR 1780 Acid chloride Stretch O-CH₂-CH₂ a- CH₂ - CH₂ - CH O-CH₂ - CH₂ Hi spliting due to neighbouring proton 3.4 1.1 (triplet ) O-CH₂-CH₃ -CH-CH po-CH ₂ -CH2 I 4.2 3.4 lol(triplet) 2.8 ! (triplet) (quartet) 1.9 querat) (triplet) (quartet)

0 ck- 173 31 57 15 t o - CH₂ - CH₂ CH₂ - CH₂ - CH P o- CH₂ - CH3 38 100 57 15

180 160 140 120 100 80 60 40 20 PPM