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vikash chandoa Grade: 12

in reimer timen rection why dichloro carbene atack at ortho position only. Why does not it attack at para position since -OH group is ortho and para directing group?

7 years ago

Answers : (1)

AKASH GOYAL AskiitiansExpert-IITD
419 Points

Dear Vikash

Ortho hydroxy benzaldehyde(salicaldehyde ) is more stable due to INTRAMOLECULAR HYDROGEN BONDING and is found to be the major product. when base abstracts H+ from phenol then phenoxide ion is formed which resonates at ortho and para position and then :CCl2 carbene(which is a singlet carbene) attacks the anion mainly at ortho position and then oh- nucleophiles replace both cl- ions to form CHO(its h forms H-bond with O of phenol from ortho position) group with the release of water. although para pdt is minorly formed.

All the best.




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7 years ago
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