JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Which one of the following is likely to give a precipitate with solution ?
- A
- B
- C
- D
View written solutionFree
Correct answer: B
-
Principle of the test with
Silver nitrate solution is commonly used to test whether a halide ion can be released from an organic halide.
- If the compound easily ionizes to give , , etc., then a precipitate of silver halide forms.
- For chloride:
Thus, compounds that undergo easy nucleophilic substitution / ionization with release of halide ion give a precipitate.
-
Examine each option
Option A: (chloroform)
- The chlorine atoms are attached to a carbon bearing hydrogen and three chlorines.
- It does not ionize easily to release in solution.
- Hence, it is not likely to give a precipitate.
Option B: (tert-butyl chloride)
- This is a tertiary alkyl halide.
- Tertiary halides undergo substitution very easily by the mechanism because they form a stable tertiary carbocation:
- The released reacts with :
- Therefore, this compound will give a precipitate.
Option C: (carbon tetrachloride)
- This compound does not undergo hydrolysis/ionization easily.
- No easy release of occurs.
- So it is not likely to give a precipitate.
Option D: (vinyl chloride)
- Here chlorine is attached to an hybridized carbon.
- Vinyl halides are very resistant to nucleophilic substitution because the bond has partial double bond character due to resonance.
- Hence, it does not readily release .
- So it is not likely to give a precipitate.
-
Conclusion
Only tert-butyl chloride readily gives with solution.
Therefore, the correct option is:
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