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Chapter 18: 27 P (page 709)

Draw all products formed when m-chlorotoluene is treated with KNH2inNH3

Short Answer

Expert verified

Three possible products:

Step by step solution

01

Potassium amide

Potassium amide KNH2 is an inorganic reagent used as a strong base in the nucleophilic substitution of an aromatic ring.

Treatment of aryl halides with a strong base like KNH2in the presence of NH3 produces the reactive intermediate, benzyne.

02

Reaction of aryl halide and potassium amide

The reaction of m-chlorotoluene with KNH2 in the presence of NH3 produces two possible benzyne reactive intermediates.

Benzyne upon further treatment with KNH2in the presence of NH3, produces three possible products.

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Most popular questions from this chapter

Explain why each of the following reactions will not form the given product. Then, design a synthesis of A from benzene and B from phenol C6H5OH.

Question: Explain the reactivity and orientation effects observed in each heterocycle.

a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products.

b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.

Classify each substituent as electron donating or electron withdrawing.

Draw the products formed when each compound is treated with HNO3 and H2SO4. State whether the reaction occurs faster or slower than a similar reaction with benzene.

Question: Draw a stepwise, detailed mechanism for the dienone鈥損henol rearrangement, a reaction that forms alkyl-substituted phenols from cyclohexadienones.
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