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Standard XII
Chemistry
Fischer's Esterification Process
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13. An organic compound A C5H8O3 on heating with soda lime gives B which reacts with HCN to give C. The compound C reacts with thionyl chloride to produce D which on reaction with KCN gives a compound E. Alkaline hydrolysis of E gives a salt F which on heating with soda lime produces n-butane. Careful oxidation of A with dichromate gives acetic acid and malonic acid. Give the structures from A to F with proper reason .

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Solution

Dear Student,

The step by step reactions are as follows.

As given on oxidation of A with dichromate it gives acetic acid and malonic ester that gives the information of the presence of an acid and ether group in A and as molecular formula of A is C5H8O3.
The reaction is as follows :
CH3COCH2CH2COOH →K2Cr2O7CH3COOH + HOOCCH2COOH
(i) So, A will be CH3COCH2CH2COOH.

Now on heating A with sodalime it undergo decarboxylation to give B.
The reaction is as follows :
CH3COCH2CH2COOH →sodalime / decarboxylationCH3CH2COCH3 + CO2
(ii) So, B will be CH3CH2COCH3.

Now B reacts with HCN undergo nucleophilic addition reaction over aldehyde .
The reaction is as follows :
CH3CH2COCH3 →HCN CH3CH2C(CN)(OH)CH3
(iii) So, C will be ​​CH3CH2C(CN)(OH)CH3

Now, C reacts with Thionyl chloride to give D : Nucleophilic susbstitution :
The reaction is as follows:
CH3CH2C(CN)(OH)CH3→SOCl2CH3CH2C(CN)(Cl)CH3
(iv) So, D will be CH3CH2C(CN)(Cl)CH3

Now , D reacts with KCN to give E : Nucleophilic substitution :
The reaction is as follows:
CH3CH2C(CN)(Cl)CH3→KCNCH3CH2C(CN)(CN)CH3
(v) So, E will be CH3CH2C(CN)(CN)CH3

Now, E on alkaline hydrolysis gives F :
The reaction is as follows:
CH3CH2C(CN)(CN)CH3→H2O/NaOHCH3CH2C(CH3) (COONa)2
(vi) So, F will be ​CH3CH2C(CH3) (COONa)2

Regards

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