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Q8.11:
An organic compound (A) (molecular formula \(C_{8}H_{16}O_{2}\)) 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 :

Step 1: Analyzing Molecular Formula and Functional Group

The organic compound (A) has the molecular formula $C_8H_{16}O_2$. Given that (A) undergoes acid-catalyzed hydrolysis to produce a carboxylic acid (B) and an alcohol (C), compound (A) is an ester [Per the general hydrolysis reaction: $RCOOR' + H_2O \xrightarrow{H^+} RCOOH + R'OH$].

Step 2: Identifying Alcohol (C) via Dehydration

Compound (C) upon dehydration yields but-1-ene ($CH_3-CH_2-CH=CH_2$). Dehydration of an alcohol to an alkene typically involves the removal of $-OH$ from the $\alpha$-carbon and a hydrogen atom from the $\beta$-carbon. Given the product is but-1-ene, the alcohol must be butan-1-ol ($CH_3-CH_2-CH_2-CH_2OH$) [Per the Saytzeff/Hofmann elimination logic in alcohol dehydration].

Step 3: Correlating Oxidation to determine Acid (B)

We are given that oxidation of alcohol (C) with chromic acid ($H_2CrO_4$) yields acid (B). Primary alcohols ($RCH_2OH$) oxidize to carboxylic acids ($RCOOH$) with the same number of carbon atoms. Since (C) is butan-1-ol ($C_4H_{10}O$), the acid (B) must be butanoic acid ($CH_3CH_2CH_2COOH$).

Step 4: Constructing the Ester (A)

Since (A) is an ester formed from butanoic acid ($C_4H_8O_2$) and butan-1-ol ($C_4H_{10}O$), the esterification reaction (reverse of hydrolysis) involves the loss of one water molecule: $C_4H_8O_2 + C_4H_{10}O \rightarrow C_8H_{16}O_2 + H_2O$. Thus, (A) is butyl butanoate ($CH_3CH_2CH_2COOCH_2CH_2CH_2CH_3$).

Step 5: Chemical Equations

1. Hydrolysis of (A):

$CH_3CH_2CH_2COOCH_2CH_2CH_2CH_3 + H_2O \xrightarrow{H^+} CH_3CH_2CH_2COOH + CH_3CH_2CH_2CH_2OH$

2. Oxidation of (C):

$CH_3CH_2CH_2CH_2OH \xrightarrow{[O]} CH_3CH_2CH_2COOH + H_2O$

3. Dehydration of (C):

$CH_3CH_2CH_2CH_2OH \xrightarrow{conc. H_2SO_4, \Delta} CH_3CH_2CH=CH_2 + H_2O$

Visual Representation of Molecular Transformation

Ester (A): Butyl butanoate Acid (B) + Alcohol (C) Butan-1-ol (C) But-1-ene

Final Solution: (A) is butyl butanoate, (B) is butanoic acid, and (C) is butan-1-ol.


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