5. Propose a structure for a compound, with molecular formula C8H19N, that fits the following spectroscopic data: IR: 3400 cm-¹ (single peak) ¹H NMR: 0.98 (triplet, 6H), 1.1 8 (singlet, 1H, exchanges with D₂O), 1.38 (sextet, 4H), 1.4 8 (quintet, 4H), 2.68 (triplet, 4H) 13C NMR: 13.7, 20.5, 30.4, 49.2 Explain your reasoning by assigning the peaks.

Propose a structure for the compound that fits the following description. C10H14 7.0 δ, (4H, broad singlet) 2.85 δ (1H, septet J = 8 Hz) 1.20 δ (6H, doublet J = 8 Hz) 2.28 δ (3H, singlet) IR: 825 cm-1 5(a) Degree of the unsaturation of this compound is= , 5(b) Two peaks at 2.85 δ and 1.20 δ indicate that the compound has ..........  group = 4(c) A peak at 2.28 δ indicates that the compound has ............. group=  4(d) IR absorption indicates the compound is .........-disubstituted =  4(e) The name of the compound is =

Do not give handwriting solution.

(b) The 1H-NMR spectrum of compound B, C5 H10 O2, consists of the following signals: 8 1.2 (d, 6H), 2.0 (s, 3H), and 5 (septet, 1H); contains an ester. Draw the structural formula of compound B. • You do not have to consider stereochemistry. • Explicitly draw all H atoms. ୫) C n ? ChemDoodle ® Show Hint