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In the first step, the ethanoic acid takes a proton (a hydrogen ion) from the concentrated sulphuric acid. The proton becomes attached to one of the lone pairs on the oxygen which is double-bonded to the carbon.

Now a molecule of water is lost from the ion.

The transfer of the proton to the oxygen gives it a positive charge, but it is actually misleading to draw the structure in this way (although nearly everybody does!).


Procaine is a local anesthetic drug of the amino ester group

The positive charge is delocalised over the whole of the right-hand end of the ion, with a fair amount of positiveness on the carbon atom. In other words, you can think of an electron pair shifting to give this structure:


Learn the specifics of the Fischer Esterification mechanism

Ethanoic acid reacts with ethanol in the presence of concentrated sulphuric acid as a catalyst to produce the ester, ethyl ethanoate. The reaction is slow and reversible. To reduce the chances of the reverse reaction happening, the ester is distilled off as soon as it is formed.

Synthesis of Isopentyl Acetate Via Fischer Esterification Essay

Note: You could work out precisely why that particular oxygen carries the positive charge on the right-hand side. On the other hand, you could realise that there has to be a positive charge somewhere (because you started with one), and that particular oxygen doesn't look right - it has too many bonds. Put the charge on there!

Chemistry Lab Help - Synthesis of Benzocaine? | Yahoo …

What happens next is that a proton (a hydrogen ion) gets transferred from the bottom oxygen atom to one of the others. It gets picked off by one of the other substances in the mixture (for example, by attaching to a lone pair on an unreacted ethanol molecule), and then dumped back onto one of the oxygens more or less at random.

Benzocaine was used in synthesis of …

This page looks in detail at the mechanism for the formation of esters from carboxylic acids and alcohols in the presence of concentrated sulphuric acid acting as the catalyst. It uses the formation of ethyl ethanoate from ethanoic acid and ethanol as a typical example.

Synthesis of benzocaine : OrganicChemistry - reddit

The structure for the latest ion is just like the one we discusssed at length back in step 1. The positive charge is actually delocalised all over that end of the ion, and there will also be contributions from structures where the charge is on the either of the oxygens:

Prepd by the esterification of p-aminobenzoic acid: ..

Over the past 2-years benzocaine powder has been heavily publicised for its controversial use in designer drugs as well as a cutting agent in illegal substances. It’s estimated that over 36 tonnes of cutting agents where imported into the UK in 2009-10. The Serious Organised Crime Agency (SOCA) has only been able to seize between…