The connection and fragmentation of carbon-carbon bond is always a hot topic in organic synthesis, and scientists have been finding different ways to achieve this goal. Many achievements have been made in this field. Grignard reaction and olefin metathesis reaction are the famous and typical ones. In particular, olefin metathesis provides a new way to connect sp 2 carbon and sp 2 carbon, which suits some active molecules. Therefore, the 2005 Nobel Prize in Chemistry was awarded to three scientists who made outstanding contributions to olefin metathesis. This experiment is consisted of three reactions, including the improved Grignard reaction, DMAP-catalyzed esterification, and ring closing olefin metathesis cyclization. It is helpful to understand the process and mechanism of organic reactions and enjoy the charm of organic synthesis.