Otto-Kurt maybe?
Chemistry
Level
4
Consider the following sequence of reaction; identify the intermediate A and choose the answer that represents the sum of its double bonds and oxygen atoms.
8
4
9
5
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1 solution
The following solution contains two approaches:
Approach 1:
The reagents undergo a modified Pummerer Rearrangement in which the carbonyl attacks the sulphonium ion instead of acetic acid's conjugate base, this gives:
Approach 2:
This compound has 4 double bonds ( excluding the phenyl ring ) and 4 oxygen atoms.
However,
This compound expels acetic anhydride (retro-synthetically) to generate:
This compound has 7 double bonds ( including the phenyl ring ) and 1 oxygen atom.
Hence the answer is 8