GC Reaction Question...

[allard6]

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(R)-2-bromobutane + Iodide ion in aprotic solvent ---> (S)-2-iodobutane


I thought it would be "no reaction" since iodide is a better leaving group than bromide... What am i missing? 😕😕

 

[AlbinoPolarBear]

(R)-2-bromobutane + Iodide ion in aprotic solvent ---> (S)-2-iodobutane


I thought it would be "no reaction" since iodide is a better leaving group than bromide... What am i missing? 😕😕

Iodine is also an awesome nucleophile for SN2 reactions.

It will kick out the Bromine.

 

[Golfguy]

(R)-2-bromobutane + Iodide ion in aprotic solvent ---> (S)-2-iodobutane


I thought it would be "no reaction" since iodide is a better leaving group than bromide... What am i missing? 😕😕

And, in aprotic solvent Br is a better nucleophile. So I think equilibrium would lie to the left.

 

[PooyaH]

Here it has nothing to do with which one is a better leaving group. Both Br and I are good leaving groups but I is better. For an SN2 reaction you need to have a strong/good leaving group and a strong nucleophile, which in this case Iodide ion is.

 

[LetsGo2DSchool]

Iodine is also an awesome nucleophile for SN2 reactions.

It will kick out the Bromine.

Think of it as I(odine) will kick Bro(mine's) ass.

Sometimes mnemonics help.

 

[allard6]

Thank you all!!! 🙂