Choose the correct set of reagents for the following conversion. [figure]
- Cl2/ anhy. AlCl3; Br2/Fe; alc. KOH
- Cl2/Fe; Br2/ anhy. AlCl3; aq. KOH
- Br2/Fe; Cl2, ; alc. KOH
- Br2/ anhy. AlCl3; Cl2, ; aq. KOH
Answer
(3) Br2/Fe; Cl2, ; alc. KOH
Solution
Step 1 – Br2/Fe: electrophilic substitution on the ring; –C2H5 is o/p-directing, the para product is major.
Step 2 – Cl2, : free-radical chlorination at the benzylic carbon (most stable benzylic radical).
Step 3 – alc. KOH: dehydrochlorination (elimination) forms the C=C.
[figure]
Other options fail: (1) and (2) put Cl on the ring with a Lewis-acid catalyst instead of on the side chain; (2) and (4) use aq. KOH, which substitutes Cl by OH (alcohol) instead of eliminating HCl.
Answer: (3)