Solveeit Logo

Question

Chemistry Question on Organic Reactions

The major product of the following reaction is P. Number of oxygen atoms present in product 'P' is _______ (nearest integer).

Answer

The reaction proceeds as follows:
Step 1: The triple bond in CH3_3C\equivC-CH3_3 is reduced to a trans-alkene using Na/liq. NH3_3:
CH3CC-CH3Na/liq. NH3CH3CH=CHCH3\text{CH}_3\text{C} \equiv \text{C-CH}_3 \xrightarrow{\text{Na/liq. NH}_3} \text{CH}_3\text{CH} = \text{CHCH}_3
Step 2: The trans-alkene undergoes oxidation with dilute KMnO4_4 at 273 K. This leads to the formation of a vicinal diol:
CH3CH=CHCH3dil. KMnO4CH3CH(OH)CH(OH)CH3\text{CH}_3\text{CH} = \text{CHCH}_3 \xrightarrow{\text{dil. KMnO}_4} \text{CH}_3\text{CH(OH)CH(OH)CH}_3
The final product P' contains two hydroxyl (-OH) groups, contributing two oxygen atoms. Number of oxygen atoms in product P':
2(from hydroxyl groups)2 \, (\text{from hydroxyl groups})

Explanation

Solution

The reaction proceeds as follows:
Step 1: The triple bond in CH3_3C\equivC-CH3_3 is reduced to a trans-alkene using Na/liq. NH3_3:
CH3CC-CH3Na/liq. NH3CH3CH=CHCH3\text{CH}_3\text{C} \equiv \text{C-CH}_3 \xrightarrow{\text{Na/liq. NH}_3} \text{CH}_3\text{CH} = \text{CHCH}_3
Step 2: The trans-alkene undergoes oxidation with dilute KMnO4_4 at 273 K. This leads to the formation of a vicinal diol:
CH3CH=CHCH3dil. KMnO4CH3CH(OH)CH(OH)CH3\text{CH}_3\text{CH} = \text{CHCH}_3 \xrightarrow{\text{dil. KMnO}_4} \text{CH}_3\text{CH(OH)CH(OH)CH}_3
The final product P' contains two hydroxyl (-OH) groups, contributing two oxygen atoms. Number of oxygen atoms in product P':
2(from hydroxyl groups)2 \, (\text{from hydroxyl groups})