Question

Formula: C₁₆H₁₈N₂O                                     IR peaks (cm^-1): 1635 (strong), 1585 (weak)

Mass Spec: base peak (m/z) = 29              UV-Vis = 325 nm (benzene = 255 nm)

¹³C: δ 134, 133, 120, 118, 110, 80, 75, 54

¹H: δ 7.97 (d, 2H), 7.23 (d, 2H), 3.92 (s, 4H), 2.82 (q, 4H), 1.72 (t, 6H)

HDI = # of carbons + 1 - 1/2 (# of hydrogens + # of halogens - # of nitrogens)

bj Fill out the following data tables based on your knowledge and analysis: Molecular Weight Functional Groups HDI Expected IR peaks pected Mass Spec Molecular lon Peak (M) UV-Vis H-NMR analysis: Chemical shift δ l Integration Fragment Symmetry? (Yes or No)

Answer 1

Molecular weight calculated from formula. Functional groups given by looking formula and IR and H NMR peaks. HDI have its own formula for calculation of index of hydrogen deficiency. M+ peak is due to molecular ion and UV data given.

H NMR are explained by value and type of multiplicity of peak

Molecular weight	254g/mol
Functional Groups	Aromatic (alkene), ether, alkyl
HDI	9
Expected IR peaks	1635 (strong) for ether, 1585 (weak) for aromatic C=C
Expected M+	254
UV-VIS	325nm (given)

1H NMR analysis

Chemical shift (ppm)	Integration	Fragment	Symmetry (Yes/No)
7.97 (d, 2H),	4.63	aromatic H	Yes
7.23 (d, 2H)	4.2	Aromatic H	Yes
3.92 (s, 4H),	2.28	methoxy group	No
2.82 (q, 4H)	1.64	amine	No
1.72 (t, 6H)	1	methyl group	Yes