Product please

7 Answers

1
Debosmit Majumder ·

will this be the product?

71
Vivek @ Born this Way ·

It depends highly on where the C14 atom is ?

1
rishabh ·

i gues debosmit is right.
first eto- will attack c14 and c-o bond will break rendering a negative charge on o.
now internal nucleophilic rxn. => o- will attack the carbon and cl- will leave.

EDIT: ^ c14 is just for marking the carbon.doesn't affect the reaction.

71
Vivek @ Born this Way ·

Your mechanism is right.

But even if OEt attacks dirrectly at cl- attached carbon in an SN2 fasion, the product will be same ?

So why it isn't so?

1
rishabh ·

beacause the epoxide ring is more reactive.

262
Aditya Bhutra ·

because OEt will attack from least hindered site . (ie the C14 atom)
hence in the product given by debosmit, the rightmost carbon is C14

71
Vivek @ Born this Way ·

Thanks..

My doubt was cleared regarding steric hindrance with 3D viewer..

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