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QUESTION

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

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.