0 votes
13 views
ago in Organic Chemistry by (139k points)
What is the mechanism of the nucleophilic substitution reaction of 2-bromopentane with sodium methoxide? Provide the complete reaction pathway and identify the intermediate(s) and the products at each step.

1 Answer

0 votes
ago by (139k points)
The nucleophilic substitution reaction of 2-bromopentane with sodium methoxide follows an SN2  substitution nucleophilic bimolecular  mechanism. Here's the complete reaction pathway:1. Sodium methoxide  NaOCH3  dissociates into sodium  Na+  and methoxide  CH3O-  ions. Methoxide is a strong nucleophile.2. The methoxide ion  CH3O-  attacks the electrophilic carbon atom  C2  of 2-bromopentane from the backside, opposite to the bromine atom. This backside attack leads to the inversion of configuration at the carbon center.3. As the methoxide ion forms a bond with the electrophilic carbon, the carbon-bromine bond starts to break, and the bromine atom leaves as a bromide ion  Br- .4. The product is 2-methoxypentane, and the leaving group is the bromide ion  Br- . The sodium ion  Na+  associates with the bromide ion to form sodium bromide  NaBr .Overall reaction: 2-bromopentane + sodium methoxide -> 2-methoxypentane + sodium bromideThere are no intermediates in this reaction, as the SN2 mechanism involves a single concerted step. The products are 2-methoxypentane and sodium bromide.
Welcome to Sarvan Science Q&A, where you can ask questions and receive answers from other members of the community.
...