Identify compounds A and E in the following reaction sequence. [figure]
- A = [figure] E = [figure]
- A = [figure] E = [figure]
- A = [figure] E = [figure]
- A = [figure] E = [figure]
Answer
(2) A = [figure] E = [figure]
Solution
Step 1 (bromination): –C2H5 is o/p-directing and –NO2 is m-directing; both direct Br to the position ortho to –C2H5 (meta to –NO2).
⇒ A = 2-bromo-1-ethyl-4-nitrobenzene [figure]
Step 2: Sn/HCl reduces –NO2 to –NH2 ⇒ B = 3-bromo-4-ethylaniline
Step 3: NaNO2/HCl at 273–278 K ⇒ C = diazonium salt (– N2 Cl )
Step 4: C2H5OH reduces – N2 to –H ⇒ D = 1-bromo-2-ethylbenzene
Step 5: alkaline KMnO4 oxidises the whole side chain to –COOH ⇒ E = 2-bromobenzoic acid [figure]
Answer: (2)