The major product of the following reaction is: [figure]
- 6-Phenylhepta-3,5-diene
- 6-Phenylhepta-2,4-diene
- 2-Phenylhepta-2,4-diene
- 2-Phenylhepta-2,5-diene
Answer
(3) 2-Phenylhepta-2,4-diene
Solution
The substrate is CH3-CH(C6H5)-CHBr-CH2-CHBr-CH2-CH3, i.e. 3,5-dibromo-2-phenylheptane (C-1 = the methyl on the benzylic carbon).
Excess alcoholic KOH with heat removes two molecules of HBr (two β-eliminations).
Elimination at C-3: the β-H on C-2 is benzylic and tertiary; removing it gives the more substituted double bond C2=C3 that is also conjugated with the benzene ring (Saytzeff product, extra resonance stability).
Elimination at C-5: a β-H can come from C-4 or C-6; removing it from C-4 gives C4=C5, which is conjugated with C2=C3 (conjugated diene is more stable).
Product: CH3-C(C6H5)=CH-CH=CH-CH2-CH3, a fully conjugated system (ring + C2=C3 + C4=C5).
IUPAC name: 2-Phenylhepta-2,4-diene.
Answer: (3)