Question

Gas Chromatography Mass Spectrometry (GC-MS) Data Interpretation Section T Sam T llam T2pm Sam R 11am GC reten- tian time (min) Functional group(s) based on IR bond absorptions Parent radical cation m/z Molecular Degrees formula unsat uration Compound structure and IUPAC name Bolling point "C) carefully draw each fragment structure with the appropriate formal charge. You need only show one resonance form. 57 a cleavage) 43 (a-cleavage) 1.94 aldehyde or ketone CHO I 72 73 (o-cleavage) 59 c-cleavage) 2.27 alcohol C-O 88 not detected O-H 71 (a-cleavage) 58 (McLaugherty rearr.) 43 (o-cleavage) 2.55 aldehyde or ketone C=O 86 91 (heterolytic cleavage) 5.01 aromatic C=C, sp?C-H halogen 126, 128 (3:1) C-X

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Answer 1

Bp Bip Go Retention time functional groups) based on IR Aldehyde Parent radical cation (m/2) Molecular DU structure formular on IUPAC name (5-321 0 Cht) Hn c 1.94 79.60 72 CHO 1 HC-C-CH-CH3 ketone cao 2-butanone

fragments structure 57 (2-cleavage) 43 (x-cleavage HC-8-c4c4 0 -24, Sperl cune) - (&-CH=CH2)

(Conti)-H oH 221 alcohol 88 Sto o che & - CHiCtiz 102c (5+1)-12/ 2-methylbutanol-2 = 66 2-methyl-2-butanol

59 (x-cleavage) 73 (x-cleavage) oH 7 t HICH HECH - H HE - -C- CH - H - CH CH₂ CH3 SOC-CH-CH3 CH₃

CHO 86 CHO DU = (C+1) - 14-22 255 aldehyde aldehyde ketone o 2.55 loic - = (5+1) - 102 - 1 HC-OCH-CH-CH3 (2-pentanone)

fragmentation 71 (&-cleavage) 58 (M. Lafferty rearrangement) - gedo.com (2nd) con CH CH C-CH-CH-CH. 2 2 CH CH₂ - СН 00

CHO 126 128 1790 (Sn +) Hot The = (1+1) - 1 - 2 aromatic cal sp²C-H halogen с-х ( 7 5.01 benzyl chloride - 8-4 - 4