An organic compound(A)(molecular formula\( C_8H_{16}O_2\))was hydrolysed with dilute sulphuric acid to give a carboxylic acid(B)and an alcohol(C).Oxidation of(C)with chromic acid produced (B).(C)on dehydration gives \(but-1-ene\).Write equations for the reactions involved.
An organic compound(A)(molecular formula\( C_8H_{16}O_2\))was hydrolysed with dilute sulphuric acid to give a carboxylic acid(B)and an alcohol(C).Oxidation of(C)with chromic acid produced (B).(C)on dehydration gives \(but-1-ene\).Write equations for the reactions involved.
Solution and Explanation
An organic compound A with molecular formula \(C_8H_{16}O_2\) gives a carboxylic acid(B)and an alcohol(C)on hydrolysis with dilute sulphuric acid.Thus,compound A must be an ester.Further, alcohol C gives acid B on oxidation with chromic acid.Thus,B and C must contain equal number of carbon atoms.
Since compound A contains a total of 8 carbon atoms,each of B and C contain 4 carbon atoms.
Again,on dehydration,alcohol C gives \(but-1-ene\).Therefore,C is of straight chain and hence,it is \(butan-1-ol\).
On oxidation,\(Butan-1-ol\) gives butanoic acid.
Hence, acid B is butanoic acid.Hence,the ester with molecular formula \(C_8H_{16}O_2\)2 is butylbutanoate.
All the given reactions can be explained by the following equations.
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\((v)\)
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Concepts Used:
Aldehydes, Ketones and Carboxylic Acids - Chemical Reactions
Chemical Reactions of Aldehydes and Ketones:
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