0 votes
28 views
ago in Organic Chemistry by (1.7k points)
Which rearrangement reaction occurs when 2-bromopentane is treated with sodium ethoxide in ethanol, and what is the mechanism of this reaction?

1 Answer

0 votes
ago by (2.5k points)
The rearrangement reaction that occurs when 2-bromopentane is treated with sodium ethoxide in ethanol is the E2 elimination reaction, which leads to the formation of an alkene. The mechanism of this reaction is as follows:1. Sodium ethoxide  NaOEt  acts as a strong base in this reaction. The ethoxide ion  EtO-  abstracts a proton  H+  from the -carbon  carbon adjacent to the carbon attached to the bromine atom  of 2-bromopentane. 2. Simultaneously, the electrons from the C-H bond that was broken form a double bond between the -carbon  carbon attached to the bromine atom  and the -carbon.3. At the same time, the C-Br bond breaks, and the bromide ion  Br-  leaves as a leaving group.4. The final product is an alkene. In this case, there are two possible products: 2-pentene  the major product  and 3-pentene  the minor product . The major product is formed according to Zaitsev's rule, which states that the more substituted alkene is the major product in an elimination reaction.Overall, the E2 elimination reaction occurs in a single concerted step, with the base abstracting a proton, the formation of the double bond, and the departure of the leaving group happening simultaneously.
Welcome to Sarvan Science Q&A, where you can ask questions and receive answers from other members of the community.
...