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.