Each of these smaller pieces corresponds to at least one reaction or step.
Organic Syntheses by Oxidation with Metal Compounds
Paracetamol can also be prepared in three steps starting from phenol. How can we go backward from paracetamol to phenol? The first step is the same as above; we remove the amide to get to the free amino group and 4-Aminophenol. Then we have to think that the amino group can be prepared by reduction of a nitro group.
The chemical compound that has an OH group and a nitro group on the benzene ring, facing each other is called para nitrophenol IUPAC: 4- nitrophenol. The last step: how to insert a nitro group on the phenol ring? This can easily be done using an electrophilic aromatic substitution, something you have learned in school when you learned about the nitration of benzene.
So see below how the retrosynthesis looks like:. Now see how the forward synthesis the synthesis the chemist will perform in the lab looks like compared to the retrosynthesis we just did:. However, how can we be sure that the nitration will take place on the carbon opposite the OH of phenol and not anywhere else?
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The -OH can activate the benzene ring due to one of the lone pair of electrons on the oxygen group The donation of the oxygen's lone pair into the ring system increases the electron density around the ring. Phenol has more activating effect on some positions around the ring than others. That means that incoming groups will go into some positions much faster than they will into others.
You will learn why at university. That means that incoming groups like the nitro group in our paracetamol example will go into the 2- position next door to the -OH group or the 4- position opposite the -OH group. SynArchive is a free web based application that allows you to browse a growing database of organic syntheses. Unlike most chemical synthesis shown on the web, the sequence of reactions is clear, precise and unambiguous.
SynArchive - The Organic Synthesis Database
You can search for molecule's name and author's name. Synarchive helps chemistry students and chemists all over the world. If you enjoy our website and find it useful, please support us by making a donation. SynArchive : A total synthesis database SynArchive is a free web based application that allows you to browse a growing database of organic syntheses. Browse available syntheses Browse syntheses by molecule Browse syntheses by principal investigator Browse syntheses by date Browse syntheses by carbon count.
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