A Chloro-ether-diene Reaction
Chemistry
Level
3
For the above series of reactions, choose which option below represents the major product.
David's Organic Chemistry Set
David's Physical Chemistry Set
None
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1 solution
Firstly, heat will cause a C l a i s e n r e a r r a n g e m e n t to occur.
F r i e d e l − C r a f t s A c y l a t i o n occurs next when B e n z e n e and A l C l 3 are added
H y d r o c h l o r i n a t i o n occurs on the terminal double bond; this will follow M a r k o v n i k o v X ′ s r u l e .
Lastly, the re-addition of A l C l 3 causes F r i e d e l − C r a f t s A l k y l a t i o n to occur. The cation formed will be isolated, thus rearrangements will not occur before joining the benzene ring.
A n s w e r → D