Why don't bromide ions react with methoxide ions?

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Answer 1 · 2016-05-31T02:19:13

There are several reasons:

There are several reasons:

1. The two species repel each other.

$"CH"_3"O"^"-"$ has a negative charge — it is not neutral.

Hence, $"Br"^"-"$ and $"CH"_3"O"^"-"$ will repel each other.

2. $"Br"^"-"$ is an extremely weak base.

HBr is a very strong acid, so its conjugate base $"Br"^"-"$ is an extremely weak base.

$"Br"^"-"$ has no tendency to remove $"H"^+$ from anything.

3. The product of the attack would be quite unstable.

$"Br"^"-" + "CH"_3"O"^"-" → "HBr " + "H" stackrel("-")("C")"O"^"-"$

The repulsion between negative charges on adjacent atoms makes the product a high-energy species.