Question

Baeyer Villiger

Can someone explain the GCMS of this sample?

This was the procedure:

A solution of acetophenone, 20 mmoles, and metha-chloroperbenzoic acid (mCPBA)

36mmoles, are stirred in 50mL of distilled water at 80°C for 4 h and monitored by

TLC (eluent: ethyl acetate). The reaction mixture is cooled to room temperature and

extracted with dichloromethane (3x30mL). The combined organic layers are

washed with saturated NaHCO3, and NaCl brine solution. The solution is then dried

with MgSO4 and the solvent removed under reduced pressure. Column

chromatography using silica gel (36.05 g) and ethyl acetate as eluent may be

performed to remove starting material acetophenone if present and instructor

recommends it. The collected fractions containing the desired product as verified by

TLC are combined and the solvent removed under reduced pressure. The phenyl

acetate is weighted and characterized.

ID : Acetic acid, phenyl ester Abundance Average of 5.286 to 5.410 min.: ND_BVilliger_1.Didata.ms 94.0 8000 6000 4000 2000 1440 320 136.1 66.0 55.0 50 60 70 ו 77 . 0 207 . 0 10 280.9 20 105.0 1201 100 110 120 m/z--> Abundance 30 190 . 9 40 80 90 דייייייייייייייייזי דייזידידזויוויןדדדדדדדדדדייזיזידיוזייווידווידי 130 140 150 160 ויחידי 170 180 100 200 210 220 240 240 250 250 270 280 #16302: Acetic acid, phenyl ester 94.0 8000 6000 4000 430 2000 136,0 15.0 10 20 270 30 56.0 55.0 . 50 80 70 77.0 80 m/z-> 40 | 105.0 100 110 90 120.0 120 130 140 150 160 170 -יידיידייידדדדדדדדדדדדדדדדד 160 190 200 210 220 240 240 250 260 270 280 זיי

Answer 1

-136 Cg Mg02 Base Phenyl acetate gives phenol ratical & CH₃CO m/ The base peak is 94.as K. 43 the phenol forms most 1 Stable fragment. Breaking of esten bona from other side gives benzene radi- Cal with 77. m/₂=77