Question

Which of the following reaction is not correct regarding the products?

• A.

  

• B.

  

• C.

  

• D.

  

Hint:

Remember: \[ \boxed{ \begin{aligned} &\text{Williamson synthesis: } \mathrm{RONa+R'X\rightarrow ROR'}, &\text{HI/HBr cleaves ethers at the tertiary carbon by }S_\mathrm{N}1, &\text{and at the methyl/primary carbon by }S_\mathrm{N}2. \end{aligned} } \]

Answer 1

The Correct Option is B

Step 1: Examine each reaction. Reaction (A) is a Williamson ether synthesis and is correct. Reaction (C) is correct because cleavage of an unsymmetrical ether with HI occurs at the tertiary carbon via the \(S_\mathrm{N}1\) mechanism. Reaction (D) is also correct since cleavage of methyl propyl ether with HBr occurs at the methyl group through the \(S_\mathrm{N}2\) mechanism.

Step 2: Check reaction (B). Although \(p\)-bromonitrobenzene can undergo nucleophilic aromatic substitution with sodium methoxide, the product shown is not correctly represented as written in the reaction. Hence, reaction (B) is the incorrect one among the given reactions.

Step 3: Choose the correct option. Therefore, the incorrect reaction is \[ \boxed{\text{Option (B)}.} \]