A compound A (C_5H_{10}Cl_2) on hydrolysis gi | vedclass

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Question

(A) Hydrolysis of a gem-dichloride yields a carbonyl compound. Since the product $C_5H_{10}O$ reacts with $NH_2OH$,it is a carbonyl compound (aldehyde

Vedclass · Accepted Answer

$CH_3-CCl_2-CH_2-CH_2-CH_3$

Vedclass · Answer

(A) Hydrolysis of a gem-dichloride yields a carbonyl compound. Since the product $C_5H_{10}O$ reacts with $NH_2OH$,it is a carbonyl compound (aldehyde or ketone). It gives the iodoform test,which indicates the presence of a methyl ketone group $(CH_3-CO-)$. It does not give Fehling's test,which confirms it is a ketone and not an aldehyde. Therefore,$C_5H_{10}O$ is $2$-pentanone $(CH_3-CO-CH_2-CH_2-CH_3)$. To obtain $2$-pentanone upon hydrolysis,the starting compound $A$ must be $2,2$-dichloropentane $(CH_3-CCl_2-CH_2-CH_2-CH_3)$.

$A$ compound $A$ $(C_5H_{10}Cl_2)$ on hydrolysis gives $C_5H_{10}O$ which reacts with $NH_2OH$,forms iodoform,but does not give Fehling's test. $A$ is:

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