Ester (The Queenly Functional Group)

Script Included (bonus hints for Fischer Esterification at end) This is an ester. Now you could memorize it the boring way, or you could remember the story of Esther. Once you know the characters, you can always identify this functional group! The star of our show is a beautiful young woman whose name, Hadassah or Esther, means star. She was a commoner (C can stand for Commoner and Carbon), but shes going to be queen. She is going to be queen because the king of Persia sent a proclamation that he was replacing his queen, and all the young women in the kingdom, including our star, had to go to the palace for a giant "picking ceremony." They got all dressed up (That C also looks like a fancy bracelet and it is right next to the O which reminds me of a crown). Our lovely commoner pleased the king. He gave her perfumes and nice smelling resins and a place in the palace. Finally, he made her his queen. The single bond between the commoner and the crown is marriage. The R group bonded to the C is our new queens cousin, Mordecai. He took care of her and advised her after her parents died. You could think R for Relative, or R for advisoRRR. It doesnt really matter what Mordecai looks like. Any R group will do. The king has his own advisor, Haman, which we can call R group prime (R'). Once again, any R group will do. But Im pretty sure Haman would like his R group to be prime while Mordecais is regular, since thats just the sort of man he was. Theres another king in the story. When you see that the carbon is double bonded to an oxygen, remember that our queen is a religious young woman who fasts and prays (yes, thats two bonds) to help her be closer to God, her Heavenly King. Now that you know everyone, lets kick it up a notch. The King's advisor became angry at the Queen's advisor because Mordecai wouldnt bow down to him. So he convinced the king (R-group prime bonded to Oxygen) to decree that the Queens advisor and all of his people would be killed on a certain day. The queens advisor (R-group bonded to Carbon) told her about this and asked her to plead with her husband for all of their lives. She was afraid to do this, because the King could have her killed if she approached him without his consent. But, she fasted and prayed to her Heavenly King for strength. (Do you realize even the bond lengths make sense in this story? Double bonds are stronger and shorter than single bonds. I know Id feel less connected to and more distant from a king that could kill me just because I came by.) After giving a couple of feasts to soften him up, the queen talked to her husband the King of Persia (Carbon single bonded to Oxygen) about this terrible plan concocted by the King's advisor (R-group prime) to kill not only her advisor and his people, but also to kill her! The king began to see that he was being used as the middle man between his advisor and the people his advisor hated. Incidentally, esters are found in fruits and flowers and perfume. What you do you think Queen Esther was surrounded by in her Persian palace? Yeah, I'm going with fruits, and flowers, and perfume. Here's another useful tidbit for you: When you name an ester, the name has two parts. The name will be in this form: alkyl alkoate. The first part is named after the R alkyl (the one attached to the oxygen), and then the second part is named after the RCO carboxylic acid, but changing the -ic acid to -ate. In other words, the king's advisor is named first, even though he advised the king for ill, and then comes the queen's advisor, who like the queen, did not eat (no ate) before the queen went to talk to the king. To name that ester, think king's advisor-yl queen's advisor-oate. For those of you going on to Organic 2, this will be a fun bonus memory trick for you. One way to make an ester is with a Fischer esterification reaction. For a Fischer esterification, the O-R' subgroup comes from the alcohol, while the RCO subgroup comes from the carboxylic acid. So an ester forms when the alcohol loses its H, the carboxylic acid loses its OH group, and then the O from the alcohol bonds to the Carbon from the RCO group. Or you could remember that the previous queen lost her position when she was Haughty and refused to visit the king and all his drunk friends (so thats an H leaving an alcohol). Then think about how the king, who always gets what he wants said, You will be my queen and all she said was, OH. And finally remember that Esther only became the Queen Esther we know when she married the king and the single bond formed between C and O. Heres a final tip: For a Fischer esterification, you need liquid alcohol. I know some fishermen who consider liquid alcohol a necessity for fishing as well.