Tropinone: spot the stereochemistry flaw

Single question

Robinson's 1917 one-pot Mannich condensation: succinaldehyde plus methylamine plus acetone-1,3-dicarboxylic acid in water at pH 5 gives tropinone. Reagents and reaction class match. Check the ring fusion at the two bridgehead carbons.

Bredt's rule for small bridged bicyclics

Robinson tropinone Mannich condensation

Cis vs trans ring fusion in [3.2.1] bicyclics

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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