JEE MainChemistryHydrocarbons
Consider the following sequence of reactions starting from benzene: Benzene CH ₃ CH ₂ CH ₂ Cl, AlCl ₃ P (major) Br ₂ , Fe Q (major) NBS, h R alc. KOH, S (major) The IUPAC name of the final major product 'S' is:
Options
- A1-bromo-4-(prop-1-enyl)benzene
- B1-bromo-4-(prop-1-en-2-yl)benzene
- C1-(2-bromopropan-2-yl)benzene
- D1-bromo-2-(prop-1-en-2-yl)benzene
Correct answer
B. 1-bromo-4-(prop-1-en-2-yl)benzene
Step-by-step solution
Step 1: Reaction of benzene with n-propyl chloride and AlCl ₃ generates a primary carbocation ( CH ₃ CH ₂ CH ₂^+ ), which undergoes a 1,2-hydride shift to form a more stable secondary carbocation ( CH ₃ CH ^+ CH ₃ ). Electrophilic aromatic substitution yields isopropylbenzene (cumene) as the major product 'P'. Step 2: Bromination of isopropylbenzene with Br ₂/ Fe occurs via electrophilic aromatic substitution. The bulky isopropyl group directs the incoming bromine predominantly to the para position due to steric hi