Structure and Properties
Malonic acid is a rather simple dicarboxylic acid, with two the carboxyl groups close together. In forming diethyl malonate from malonic acid, the hydroxyl group (-OH) on both of the carboxyl groups is replaced by an ethoxy group (-OEt; -OCH2CH3). The methylene group (-CH2-) in the middle of the malonic part of the diethyl malonate molecule is neighboured by two carbonyl groups (-C(=O)-).
The hydrogen atoms on the carbon adjacent to the carbonyl group in a molecule is significantly more acidic than hydrogen atoms on a carbon adjacent to alkyl groups (up to 30 orders of magnitude). (This is known as the α position with respect to the carbonyl.) The hydrogen atoms on a carbon adjacent to two carbonyl groups are even more acidic because on the – the carbonyl groups helps stabilize the carbanion resulting from the removal of a proton from the methylene group between them.
The extent of resonance stabilization of this compound's conjugate base is depicted by the three resonance forms below:
Read more about this topic: Diethyl Malonate
Famous quotes containing the words structure and, structure and/or properties:
“With sixty staring me in the face, I have developed inflammation of the sentence structure and definite hardening of the paragraphs.”
—James Thurber (1894–1961)
“What is the most rigorous law of our being? Growth. No smallest atom of our moral, mental, or physical structure can stand still a year. It grows—it must grow; nothing can prevent it.”
—Mark Twain [Samuel Langhorne Clemens] (1835–1910)
“The reason why men enter into society, is the preservation of their property; and the end why they choose and authorize a legislative, is, that there may be laws made, and rules set, as guards and fences to the properties of all the members of the society: to limit the power, and moderate the dominion, of every part and member of the society.”
—John Locke (1632–1704)