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Haloalkanes and Haloarenes
Wurtz Reaction
1 question from 1 paper, each with its answer.
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Concepts tested
- Symmetry of Wurtz product
All Questions
2001 AIPMT 1 question
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An organic compound A ($C_4H_9Cl$) on reaction with Na/diethyl ether gives a hydrocarbon which on monochlorination gives only one chloro derivative then, A is : -In the Wurtz reaction, two alkyl groups join: $2RCl + 2Na \xrightarrow{dry\ ether} R-R + 2NaCl$
A hydrocarbon that gives only one monochloro derivative must have all its hydrogen atoms equivalent.
From t-butyl chloride, $(CH_3)_3CCl$: $R-R = (CH_3)_3C-C(CH_3)_3$ (2,2,3,3-tetramethylbutane). All 18 hydrogens are on equivalent methyl groups, so it gives only one monochloro product.
The products from the other butyl chlorides (n-octane, 3,4-dimethylhexane, 2,5-dimethylhexane) have different kinds of hydrogen and give several monochloro products.
So A is t-butyl chloride.