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Chapter 4: Problem 56

Benzyne mechanism is operating in the nucleophilic substitution of (a) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{Cl}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\)

Short Answer

Expert verified
Answer: Compound (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\) undergoes nucleophilic substitution through the benzyne mechanism.

Step by step solution

01

Identify the compounds with aromatic rings

Among the compounds given, we need to identify the ones with aromatic rings. Aromatic rings are a key component to consider when discussing the benzyne mechanism. The compounds with aromatic rings are: (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\)
02

Determine if each compound has the halogen directly attached to the carbon of the aromatic ring

The benzyne mechanism is specific to aryl halides, which involve halogens directly attached to an aromatic ring, with no other substituents on the carbon that bears the halogen. We need to eliminate any compound that does not meet this requirement. (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}\) - Here, the chlorine is attached to an aliphatic carbon, not the aromatic ring. (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) - Similarly, the chlorine is not directly attached to the aromatic ring. (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\) - The chlorine atom is directly attached to the carbon of the aromatic ring.
03

Determine the compound that undergoes nucleophilic substitution via the benzyne mechanism

Based on our analysis, compound (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\) is the one that meets the requirements for the benzyne mechanism as it has the chlorine atom directly attached to the carbon of the aromatic ring. Therefore, the benzyne mechanism is operating in the nucleophilic substitution of compound (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\).

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