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ff151djg ff151djg
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10 years ago
Predict and draw the major product of the following reaction.? You only need to give one enantiomer.

1-methyl-cyclohexene ->> (Br2/H2O)

what is the product? what is dashed what is wedged?
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wrote...
10 years ago
Br2 is going to split, with one Br becoming Br- and the other Br+ forming a cyclic bromonium ion across the (previously) double bond, connecting the secondary carbon and tertiary carbon. Water will then attach to the tertiary carbon from the other side (if the Br+ cyclic bromonium ion is wedged, the resulting OH group will be dashed) and Br will remain on the secondary carbon. It's an anti addition. Once water is attached, O has a + charge, so another water molecule strips it of one of its hydrogens (H+), leaving an OH group behind. If you draw Br as wedged, OH must be dashed. You can draw it the other way too. The methyl group will have the opposite dash or wedge of OH.
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