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Question

The major product formed in the following reaction is

The correct answer is

To determine the major product of the given reaction, we need to analyze the reagents and conditions involved:

  1. The starting compound is pyridine. Pyridine is a heterocyclic aromatic organic compound, similar to benzene, but with one methine group replaced by a nitrogen atom.
  2. The reagents used are trimethylsilyl chloride (TMS-Cl) and a base. TMS-Cl is commonly used to protect alcohols by converting them to silyl ethers and can also react with other nucleophilic centers.

Here's how the reaction proceeds:

  1. The nucleophilic nitrogen in pyridine attacks the TMS-Cl, forming the N-trimethylsilyl pyridinium salt. This step involves the transfer of the trimethylsilyl group to the nitrogen atom.
  2. Hydrolysis (or the presence of water) then removes the silyl group, regenerating the pyridine nucleus and producing the trimethylsilyl alcohol as a by-product.

The major product of this reaction is the pyridine with a potentially modified substituent if further reactions are possible with other reagents. However, the primary interaction is with the trimethylsilyl group on nitrogen.

Given the question and options, the correct answer is the N-trimethylsilyl pyridinium salt:

This product reflects the main reactive pathway in the reaction conditions provided, where the pyridine ring remains intact, and substitution occurs at the nitrogen.

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Important Questions from Heterocyclic Compounds

  1. Compound A on Hofmann exhaustive N-methylation procedure (involving two cycles), followed by ozonolysis (i. $O_3$; ii. $Me_2S$) gives benzaldehyde, formaldehyde and 2,2-dimethylpropanedial. The structure of A is
  2. Isoquinoline on sequential reaction with benzoyl chloride and KCN followed by heating with aq. NaOH gives
  3. The major products A and B formed in the following reaction sequence are:

  4. The major product formed in the reaction of indole with NaNH$_2$ and PhSO$_2$Cl is
  5. The correct order of basicity for the following heterocycles is

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