Compound A has a parent peak of M+ = 95 m/z in its mass spectrum and shows a med
ID: 816789 • Letter: C
Question
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. The HNMR 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) can be transformed back to A by using SoCl2. Finally compound B can be transformed with lithium aluminum hydride (ether) then aqueous acid to compound C (M+ = 99 m/z).
State the reasons for the following reaction.
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. The HNMR 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) can be transformed back to A by using SoCl2. Finally compound B can be transformed with lithium aluminum hydride (ether) then aqueous acid to compound C (M+ = 99 m/z). State the reasons for the following reaction.Explanation / Answer
Aqueous acid substitutes the chloride (-Cl) in A with a hydroxide (-OH) by attachment of water at the C=O carbon of A, followed by removal of H+ ion from attached water which then displaces Cl. This process takes place by sN2.
The reaction can be reversed by adding SOCl2 which displaces water and adds itself to the acid.
The acid B then reacts with Lithium Aluminium Hydride and gets reduced to alcohol due to addition of hydride ions
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