Friedel Crafts Acylation article

Friedel Crafts Acylation article - CHM 210W Writing...

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CHM 210W Writing Assignment 1: Crafting Chemicals Friedel-ly: The Friedel-Crafts Acylation Reaction, and its Importance in Organic Chemistry 03/01/2010 Manuel Vazquez 27601129
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A common worker prepares a dynamite charge on the side of a mountain, in order to construct a new tunnel. An artist applies a bit of paint thinner to her mix, preparing to create her masterpiece mural on the side of a busy city street. A pilot joins an engineer as he performs a final check on a plane’s fuel tanks, making sure that it is well-stocked on jet fuel for the journey he is about to make. All these situations involve modifications of a chemical which is underappreciated by the layman, but highly valued by the chemist: toluene. A fairly simple chemical at first glance, toluene (Figure 2) is a derivative of another vital organic chemical called benzene Figure 1: Kekulé Structure Portrayal of Benzene Figure 2: Kekulé Structure Portrayal of Toluene (Figure 1), which consists of six carbon molecules bonded to each other in a ring formation, with carbon-carbon double bonds between every other carbon pair a set-up which forms what is known as an aromatic ring and a single hydrogen atom bonded to each molecule; in toluene, a lone hydrogen on the molecule is replaced by a methyl group, which is simply a carbon with three additional hydrogens attached. This deceptively simple molecule is of great importance to the field of organic chemistry, due to its unique properties, and its abundance, which leads to it being favored as a common starting material for various compounds. Due to its vital importance as a starting material, it is of equal importance to fully understand the nature of its chemistry, and to understand how it reacts with various reagents and compounds to form a myriad of products.
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One such reaction that can be used with toluene is known as the Friedel-Crafts acylation reaction. This reaction, discovered by Charles Friedel and James Crafts in 1877, is of enormous synthetic value; in essence, an aromatic ring is reacted with a carbon chain under conditions that force the electrons of the ring to form a bond with a particular carbon on the chain, replacing a carbon-hydrogen bond on the ring with a bond from the ring carbon to a carbon on the chain. The resulting compound can then be further modified to give the aromatic ring additional properties. Such carbon-carbon bond forming reactions are vital to organic chemists, who depend on them to form larger, complex molecules with practical applications from smaller, cheaper organic compounds which can be reacted and combined to achieve the chemist’s goal. This reaction in specific is of special value to an organic chemist, since it preserves the original structure of the carbon chain being added to the ring; in the Friedel-Crafts alkylation reaction, which is another way to add carbons to an aromatic ring, there is the possibility of the original carbon chain being rearranged in order to generate a more stable product. Additionally, as will be
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