Question

Organic Chemistry

Compound A has a parent peak of M+ = 95 m/z in its mass spectrum and shows a medium intensity, sharp infrared absorption band at 2280 cm-1.The 'H NMR spectrum of compound A shows 3 signals in a 4 :4:1 ratio.

Treatment of Compound A with hot aqueous acid generates Compound B (M+= 113 m/z; strong infrared absorption 1723, medium3350 cm-1). Compound B can be transformed back to A by using SOCI2.

Finally Compound B can be transformed with lithium aluminum hydride (ether) then aqueous acid to Compound C (M+ = 99 m/z).

Identify Compounds A, B, C. State your reasoning.


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