Question

What is the 3 step strategy of reacting NH or OH bonds w/ organometallic reagents?

Answer 1

The 3 step strategy involves a nucleophilic attack on the carbonyl carbon, followed by protonation and deprotonation steps that lead to dehydration and formation of a double bond.

Step-by-step explanation:

The 3 step strategy for reacting NH or OH bonds with organometallic reagents is a type of nucleophilic addition reaction followed by dehydration. Here is the breakdown of the steps involved in the reaction mechanism:

1. Nucleophilic attack: The nucleophile (NH or OH) attacks the electrophilic carbonyl carbon, forming a tetrahedral intermediate.
2. Protonation and deprotonation: The positive nitrogen or oxygen atom gets deprotonated, and the negative oxygen atom gets protonated, leading to a protonated intermediate.
3. Elimination of water: This step involves the protonation of the hydroxyl group and deprotonation at the nitrogen atom, resulting in the elimination of water and formation of a double bond.

These steps may occur in different environments. For instance, in a basic medium, there might be an additional need for an acid-base reaction to neutralize charged intermediates. If no sufficiently acidic group is present, an external acid may be added. In acidic or amphoteric mediums, protonation enhances the reactivity of the carbonyl group and facilitates the reaction steps.