# Tandem Reactions and Super Acids

Chemistry Level pending

You are tasked to synthesise the above compound's derivative.

You start with Succinaldehyde , Benzylamine and b-ketoglutaric acid whose formulae are $$C_{4}H_{6}O_{2}$$ , $$C_{7}H_{9}N$$ , $$C_{5}H_{6}O_{5}$$ respectively.

These compounds undergo a tandem reaction to give precursor P. Now,

• P is reduced with $$NaBH_{4}$$ and then reacts with $$NaCN$$ in presence of $$TsOH$$ to give A
• A reacts with DIBAL-H to form B after hydrolysis.
• B reacts with 2-chloro ethanol in presence of piperidine and a catalytic amount of $${H}^{+}$$ to give C after hydrolysis.
• C is now oxidised in acidic $$KMnO_{4}$$ to give D
• D is decarboxylated to give precursor E whose formula is $$C_{16}H_{21}O_{2}N$$
• E undergoes hydrogenation in presence of palladium to give the precursor F
• F forms its silver salt and on reaction with $$Br_{2}$$ gives G
• G undergoes an intramolecular reaction to form the target molecule.

You call the target molecule X and carry out the next set of reactions on it:

• X on hofmann exhaustive methylation gives an unstable compound Y
• Y immediately rearranges in presence of $${H}^{+}$$ and heat to give W
• W on mono chlorination followed by reaction with $$AgF$$ gives a compound T

T reacts with $$SbF_{5}$$ to give a complex of antimony and a very stable cation V.

However V can be thought of as a tropylium cation derivative and it exceeds the tropylium carbocation's mass by b units.

In B let a denote the sum of double bonds between carbons and the number of oxygen atoms.

Calculate the value of b - a - 1

Inspirations:

• Problem 7 in 2016's IChO
• Teleanu Florin's problem
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