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Question

The correct sequence of processes involved in the following transformation is :

The correct answer is
i. deprotonation, ii. retro-aldol reaction, iii. aldol reaction, iv. O-methylation

The given transformation involves converting a hydroxy ketone to a methoxy ketone through several steps. Let's break down the processes involved in this transformation:

  1. Deprotonation: The process begins with the deprotonation of the alcohol group, which involves removing a proton (H+) from the OH group using a base such as NaH. This forms an alkoxide ion, which is a good nucleophile.
  2. Retro-aldol Reaction: The alkoxide ion can lead to a retro-aldol reaction where the C-C bond adjacent to the alkoxide group breaks, forming an enolate and releasing an aldehyde or ketone fragment.
  3. Aldol Reaction: The enolate ion acts as a nucleophile and can attack the carbonyl group of the aldehyde or ketone fragment, reforming the C-C bond in a new configuration. This results in a new β-hydroxy ketone.
  4. O-methylation: Finally, the oxygen of the alcohol group is methylated using methyl iodide (MeI), which replaces the hydrogen of the OH group with a methyl group (CH3), resulting in a methoxy ketone.

Based on the steps outlined, the correct sequence of processes involved in the transformation is:

  • i. deprotonation
  • ii. retro-aldol reaction
  • iii. aldol reaction
  • iv. O-methylation

Therefore, the correct answer is the process sequence: deprotonation, retro-aldol reaction, aldol reaction, and O-methylation.

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Important Questions from Organic Reaction Mechanisms

  1. The correct order for the relative rate of esterification of I, II, and III with p-nitrobenzoyl chloride is 

  2. The Hammett plot for the following transformation is :

  3. The relative order of rate constants in the following transformations are

  4. The correct order of basicity for the following compounds is

  5. The intermediates involved in the following reaction are

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