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Chapter 7: Problem 9

How will you distinguish between chlorobenzene and benzyl chloride?

Short Answer

Expert verified
Answer: Chlorobenzene and benzyl chloride can be differentiated using their reactivity with sodium hydroxide (NaOH) or Finkelstein reaction. Chlorobenzene does not react with sodium hydroxide or undergo Finkelstein reaction, whereas benzyl chloride reacts with sodium hydroxide to form benzyl alcohol and undergoes Finkelstein reaction to form benzyl iodide.

Step by step solution

01

Understand the structures of chlorobenzene and benzyl chloride

Chlorobenzene has a chlorine atom directly attached to the benzene ring (aromatic ring). Chlorobenzene: C6H5Cl Benzyl chloride has a chlorine atom attached to the benzyl group, which is a carbon atom attached to the benzene ring. Benzyl chloride: C6H5CH2Cl Before moving forward, make sure to understand these structural differences, as they will play a crucial role in differentiating these compounds.
02

Reaction with sodium hydroxide (NaOH)

Sodium hydroxide (NaOH) is a strong base, and it reacts with benzyl chloride, but not with chlorobenzene. This is because the carbon-chlorine bond in benzyl chloride is more reactive and can undergo nucleophilic substitution reactions easily. When benzyl chloride reacts with sodium hydroxide (NaOH), it forms benzyl alcohol and sodium chloride: C6H5CH2Cl + NaOH -> C6H5CH2OH + NaCl Chlorobenzene does not react with sodium hydroxide because the carbon-chlorine bond in chlorobenzene is less reactive due to being a part of an aromatic ring. The aromatic ring has a partial double bond character, which makes it difficult to break the carbon-chlorine bond.
03

Finkelstein reaction

Finkelstein reaction is a halogen exchange reaction that takes place in the presence of sodium iodide (NaI) in acetone. It is more reactive with benzyl chloride than with chlorobenzene due to the reasons mentioned earlier. Benzyl chloride will react with sodium iodide in acetone to form benzyl iodide and sodium chloride: C6H5CH2Cl + NaI -> C6H5CH2I + NaCl Chlorobenzene does not react with sodium iodide under these conditions because it is less reactive and its carbon-chlorine bond is more difficult to break.
04

Conclusion

To distinguish between chlorobenzene and benzyl chloride, you can use their reactivity with sodium hydroxide (NaOH) or Finkelstein reaction. Chlorobenzene is less reactive and does not react with sodium hydroxide or undergo Finkelstein reaction, while benzyl chloride will react with sodium hydroxide to form benzyl alcohol and undergo Finkelstein reaction to form benzyl iodide.

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