organic doubt

Why is cyclopropane forming from an alkene in Simmons Smith reaction?
Isn't dat increasing d strain...i mean isn't d product more unstable dan d reactant????
Heres wat i got for d reaction mechanism...

1 Answers

71
Vivek @ Born this Way ·

The for R groups on the alkene are under steric strain due to neighboring groups. Moreover, their constant inductive effect increases electron location on the -ene bond. This favors the addition of CH2I2 and also relaxes the steric strain by giving a near tetrahedral geometry at the two carbon atoms.

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