experiment 7 - yMaking an ester, simply a derivative of a...

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yMaking an ester, simply a derivative of a carboxylic acid and an alcohol. The problem with making an ester is that our electrophile and nucleophile, the basic reaction when we start with the two is that the nucleophile is the oxygen on the alcohol and it will attack the electrophile which is the carbon atom on the carbonyl on the carboxylic acid. The carbon though is not a great electrophile and the OH is not a great nucleophile, and the strength is not enough to overcome that. Reactants are basically not strong enough. Heat won’t help overcoming it either though, it doesn’t work. You have to change the reactants. One of them is the nucleophile, we can use a stronger version of it, an oxide salt. IT’s definitely powerful enough to react with the carbonyl, but that wouldn’t be the reaction. The proton would be taken away by the oxide salt because they are very very strong bases. We can also try changing an electrophile then. Even though it overcomes the energy needed, a second reaction would take place that we wouldn’t want to have. We can try working with electrophiles. One of them is to use acyl halide, it’s a good electrophilic carbon and reacts readily with alcohol to form an ester. In teaching labs, it’s hard to do because you can’t really buy them, and to make these is tricky and dangerous, so we don’t do it. We can also try anhydride
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experiment 7 - yMaking an ester, simply a derivative of a...

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