show the mechanism for the formation of methyl benzoate from methyl alcohol and

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Explanation / Answer

Not possible to draw them in text, other than to describe in words. The overall equation is C6H5COOH + CH3OH ---> C6H5COOCH3 + H2O First step is protonation of the carbonyl O of benzoic acid, so draw arrow from that O atom to an H+, and another arrow from the C=O bond to the carbonyl O atom. This will give you a structure that has two -OH groups on the C atom, and don't forget to place the positive charge there as well. Second step is for the lone pair of electrons on the O atom of CH3OH to bond to the positively charged C atom. The intermediate structure has two OH groups and the OHCH3 group bonded to the C atom now, and the positive charge has moved to the methanol O. To show this you draw the curly arrow from the O lone pair to the C+, and a curly arrow from the methanol O-H bond to the methanol O atom. Third step, the electrons from one of the C-OH bonds captures the H+ from the intermediate structure. Draw a curly arrow from that bond to the H+. This will leave a + charge on the C atom again. To get rid of that and complete the reaction sequence, the electrons from the O-H bond shift to refrm the C=O bond, so draw a curly arrow from the O-H bond to the +C-O bond and finish up with the final structure of methyl benzoate.

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