Question

MASS % of Base Peak 1387 S47 677 957 123 50 60 70 80 90 100 110 120 130 140 awamp % Transmittance -2958 -2870 -16701 -13811 -1246 -903 STS TTT 4000 3000 1000 2000 Wavenumber (cm-') 'H NMR 300 MHz N 1750 1740 Hz 640 Hz 570 560 Hz 300 290 Hz 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm 13C/DEPT NMR 75.5 MHz 200 180 160 140 120 100 80 60 40 ppm

please help me figure out what the compound is.

thanks

Answer 1

Answer D Mass mle = 138(M+.), 123, 95, 82(160) base Peak, 67, 54. The molecular weight of compound is 138 using Rule ols 13 138 = 10.61 The possible number of carbon atom in Compound is 10 according to ruleos 13. 2) IR 2958 m 2 -CLH 13 280 cm / =c-H 1381 1670 cm = conjugated carbonyl group (yo) = -e=c- conjugated (=c band. The IR indicate in Compound conjugated carbonyl system is present. (š=ç-c=o) 8) Molecular Formula on the basic ok mass, IR and C-13 NMR the Possible molecular formula is CgH140. C-13 NMR indicate the 8 signal and IR represent presence of carbonyl group. Thus compound has 8 types of carbon atom and one cseygen. Two Carbcons atoms are equivalent. Degree of Unsaturahim = 3 The three degree of Unsaturah on indicate the presence of one (=c- boord, one po bond ond one sing in given molecule,

4) TH-NMR S 0.9 ( 2.4mm = 6H, Singlet) = 0 -1.8( 1-2 mm = 3H, doublet ) = -H 01 c4cc-4 2.11 0.8mm = 2H Singlet) 5 -CH-=- 2:2 (0.8 mm = 2H, Singlet) => -CH-G- 5.8 (0.4mm= 1H, quooter) - CHN 5) 136-Nmſ DEPT-135 - Prolom decoupled. 25, 29,35, 45, 52, 125, 160, 200 DEPT-135 - 25, 29, 125. ( up = CH1 CH2 45, 52 () down 3 -CH- DEPT-90 -5 125 (9) 3 =4H on the basic ols DEPT-135 and DEPT-90 25(9) > CH3- 29(9) 2016– (strong) 35(s) 5-4- 456t) -> -che- 52(t) — cheg 125(d) → =<-H 160(s) → 1-4-h 200(S) -g- $ 35, 160, 200 absent in DEPT-135, DEPT-90, this indicate these carbon are quarternary carbon

on the basis of IR, NMR and Cmr the possible structure of Compound is CH₂L- 1.8(d) 2.1(s) hn 5.8(9) a " H 0.9(5) 2.2(s) 160(s) - 2512) 125(d) 4567) 1 (1 - bo200 152() 2919) 35(5) Mass - Fragmentation f. 20 - Home teo o m12138 m2=123 mI2 = 82 H Hansker than 10. december 1979 m12295