Chapter 30: Retrosynthetic Analysis | Organic Chemistry by Clayden - Greeves - Warren

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In this video, we will explain Retrosynthetic Analysis. This is the series of videos on the book of Organic Chemistry by Jonathan Clayden, Nick Greeves and Stuart Warren. This organic chemistry video tutorial focuses on Chapter 30 (Retrosynthetic analysis).

Most of the chemistry you have learned so far has concentrated on reactions (questions like ‘what do you need to add to X to get Y?’) or on products (questions like ‘what will happen if X and Y react together?’). Now we’re looking at starting materials (questions like ‘what X and Y do you need to react together to make Z?’). We’re looking at reactions in reverse, and we have a special symbol for a reverse reaction called a retrosynthetic arrow (the ‘implies’ arrow from logic).

One of the new skills you want to develop is to figure out how a particular compound can be made.  This involves "thinking backward":  analyzing what key bonds are present in the target molecule and recognizing what reactions you know that will make one (or more) of those.  Usually there will be more than one solution, and your task at that point is to select the one that is likely to give the highest yield with the least effort; issues like hazards and waste also factor in.

The constant goal of a retrosynthetic analysis should be to reduce the molecule to similarly sized building blocks of lower or similar complexity. This simplification should be continued until you reach molecules which are commercially available. The two main operation of a retrosynthetic analysis are: 1) Functional group interconversions (FIG) and 2) bond disconnections. Functional group interconversion (FGI) Many functional groups can be interconverted into each other, e.g. oxidation of an alcohol gives an aldehyde, further oxidation a carboxylic acid. Many organic transformations can be used to do FGIs. Carbonyl groups are particular useful in this respect. The reactivity of the carbonyl group can be masked during synthesis as double bond (ozonolysis for FGI into aldehyde) or dioxolane until needed.

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4 سال پیش در تاریخ 1399/07/20 منتشر شده است.
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