Draw the structure of the bromohydrin formed when (E)-2-hexene reacts with Br, H20. Use the wedge hash bond tools to indicate stereochemistry where it exists.

• If the reaction produces a racemic mixture, draw both stereoisomers.

Separate multiple products using the - sign from the drop-down menu.

a

С P

opy to

2

2/10

. [+

See explanation and image attached

Explanation:

The addition of a halohydrin to an alkene proceeds via the bromium cyclic intermediate.

The bromine dissociates heterolytically and attacks the (E)-2-hexene yielding the brominuim ion intermediate. This is now attacked by water with a consequent loss of H^+ to yield the final product.

Since the reaction involves a flat and planar carbocation intermediate, racemization is possible, thereby leading to the two stereoisomers shown in the image attached to this answer.