Which stereoisomer of 3-hexene forms a meso compound when it reacts with #Br_2# ?

1 Answer
May 21, 2015

trans-Hex-3-ene forms a meso compound when it reacts with bromine.

The bromination of an alkene involves the formation of an intermediate cyclic bromonium ion, followed by the anti-addition of a bromide ion to form the product.


The rigidity of the ring controls the stereochemistry of the reaction.

This means that the bromination of a trans alkene gives a meso dibromide.

For example, the bromination of trans-but-2-ene yields a meso compound.


Similarly, the bromination of hex-3-ene gives meso-2,3-dibromohexane as the product.


Attack of #"Br"^-# at C-3 gives (#3S,4R#)-3,4-dibromohexane.

Attack of #"Br"^-# at C-4 gives (#3R,4S#)-3,4-dibromohexane.

These two structures are superimposable on each other, so the product is a meso compound.