Question

An organic compound $A(C_4 H_9 C1)$ on reaction with Na/diethyl ether gives a hydrocarbon which on monochlorination gives only one chloro derivative, then A is

• A. t-butyl chloride
• B. s-butyl chloride
• C. iso-butyl chloride
• D. n-butyl chloride

Answer 1

The Correct Option is A

The given problem involves determining the identity of an organic compound $A(C_4H_9Cl)$ which, on reaction with sodium in diethyl ether, forms a hydrocarbon that yields only one monochloro derivative upon chlorination. Let's analyze each option:

1. t-butyl chloride:
   • Structure: (CH_3)_3CCl
   • When reacted with sodium in diethyl ether (Wurtz reaction), forms 2,2,3,3-tetramethylbutane.
   • This particular hydrocarbon can give only one monochlorinated product as all hydrogens are equivalent.
2. s-butyl chloride:
   • Structure: (CH_3CHClCH_2CH_3)
   • The resulting hydrocarbon after Wurtz reaction will have different hydrogens leading to multiple monochloro derivatives.
3. iso-butyl chloride:
   • Structure: (CH_3(CH_2)_3Cl)
   • Like the others besides t-butyl chloride, this would also have different hydrogens leading to multiple derivatives.

Conclusion: The only compound A that fulfills the condition of forming a hydrocarbon yielding a single monochloro derivative upon chlorination is t-butyl chloride.