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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?

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?

Grade:12

1 Answers

AKASH GOYAL AskiitiansExpert-IITD
420 Points
13 years ago

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.

AKASH GOYAL

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