We are just about 2 weeks away from wrapping up the semester for ochem 2 at my college and one of our final projects is that we are given a molecule and are tasked with doing a retro synthesis on the molecule and go all the way back to produce the molecule until we can't go back anymore (think benzene or carbon).
Long story short here is the molecule that was personally assigned to me: https://imgur.com/e5S1Tw7
Initially my thoughts is that I see some double bonds which indicates to me Wittig reactions? Is stereochemistry relevant here? Like do I need to worry about the R on the yilde being a phenol or a CH3 and therefore producing the E or Z product?
Other things that jump out at me I see the ether group their so I would assume the last step in my retro synthesis would be to make an ether with alcohol or an alkyl halide?
Also I assume their is a ketone their because of the wittig reaction and so I guess we can do alpha/beta aldol?
My issue with this project is getting started, I am not sure how and where to start, do I attempt to split my molecule in two halves and then start synthesizing each half? Do I not do two halves and instead start off with benzene group which has a methyl group and is therefore going to be o/p director but it can be oxidzed into an ethyl group? I am not sure why I would want to oxidze the methyl group on the benzene to the ethyl group?
I will def be doing some reading here on aromatic substitutions, wittig reactions and aldol reactions but any pointers or things that jump out at you guys when you see this please shoot them my way! For those who love retrosynthesis as well please give me all the tips!
Some things we learned this semester but are not limited to use in this project are: diels-alder, aromatic systems, aldehyde, ketones,carboxylic acid and their synthesis and reactions. Also learned about carbonyl condensations and finally learned about carbohydrates and carbons. Again we don't only have to use those, we can use any information from the internet.