Reaction of (CH3)2CH-CH2-OH with SOCl2

The reaction of (CH3)2CH-CH2-OH with SOCl2 is a substitution reaction, where the hydroxyl group (-OH) of the alcohol is replaced by a chloride ion (-Cl) from the SOCl2 molecule. This reaction is known as the Lucas test, which is used to differentiate between primary, secondary, and tertiary alcohols based on their reactivity towards SOCl2.

Mechanism of the Reaction

The reaction mechanism involves the following steps:

1. SOCl2 reacts with water to form HCl and SO2.

SOCl2 + H2O → HCl + SO2

2. The HCl produced in step 1 protonates the alcohol, making it more reactive towards the chloride ion.

(CH3)2CH-CH2-OH + HCl → (CH3)2CH-CH2-OH2+ Cl-

3. The chloride ion then attacks the protonated alcohol, forming a chloroalkane as the major product.

(CH3)2CH-CH2-OH2+ Cl- → (CH3)2CH-CH2-Cl + H2O

Major Product

The major product of the reaction between (CH3)2CH-CH2-OH and SOCl2 is (CH3)2CH-CH2-Cl, which is a chloroalkane. This is because (CH3)2CH-CH2-OH is a secondary alcohol, and secondary alcohols react relatively quickly with SOCl2 in the presence of HCl to form chloroalkanes.

Conclusion

The reaction of (CH3)2CH-CH2-OH with SOCl2 in the presence of HCl yields (CH3)2CH-CH2-Cl as the major product. This reaction is widely used to differentiate between primary, secondary, and tertiary alcohols based on their reactivity towards SOCl2.