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I need to draw the arrow push mechanism for this. All of the steps are stated, i

ID: 1015145 • Letter: I

Question

I need to draw the arrow push mechanism for this. All of the steps are stated, its just drawing out the arrows. Help please!

Starting with Acetic Acid...

The starting material of this synthesis is acetic acid, which is a two carbon compound. This becomes acylated with another acetic acid and the reaction begins. Tosylate, known as OTS, is used to protonate one of the acetic acids. The other acetic acid will bond to the first acetyl group by the electrons of its hydroxide. This process breaks the double bonded oxygen to a single bonded oxygen. The central oxygen of the molecule is deprotonated as an OH group on the carbon-2 is protonated and removed from the compound. The left over OH group must then be synthesized to continue any further in reaction. Synthesis of Salicylic acid begins with a diels alder reaction involving ethyne and vinylacteylene. This reaction, which is run under a higher temperature, results in the formation of a benzene ring. The benzene is reacted with SO3 and sulfuric acid. This begins by the protonation of the SO3 by stripping one of the protons from H2SO4. Here we get a partial positive charge on the HSO3. With the HSO+ now as an electrophile, the benzene will then react with it and sulfonation will occur. This benzenesulfonic acid must then be converted to a phenol. This can be done by nucleophilic addition of NaOH and heat. Next, the phenol will undergo ortho-acylation by carbonylchloric acid, which results in the formation of salicyclic acid. Now that we have both of our reagents present, the salicylic acid and ethanoic anhydride can react. This is done by protonation of the ethanoic acid. This allows the OH group in the salicylic acid to attack carbon 2 of the Et. Anhydride. The OH group is then deprotonated by the central oxygen. Electrons on the oxygen that was protonated first are moved to form a double bond, which breaks off the HOOCH3, leaving us with aspirin as a product. To Form our salbutamol from the aspirin, the aspirin is reacted with methano and sulfuric acid. This reaction begins by deprotonating the methano, which gives us CH3O- to act as the base. This then attacks our COOH group, breaking the double bonded oxygen, and causing a negative charge. The OH group is then protonated by H2SO4. The extra lone pair on the oxygen moves back into a double bond, which breaks off the water molecule and dehydrates the compound. The resulting compound is reacted with ALCL3 and ClCOCh3. This begins by the chlorine bonding to the AlCl3 which results in H3COCClAlCl3. One of the bonds of the benzene ring breaks and is attacked by the carbon in the electrophile. As this happens the Cl breaks off of the carbon resulting in the COCH3 group being attached to the carbon ring. The chlorine on the AlCl3 attacks the hydrogen at the carbon next to where the COCH3 was added. Next the oxygen in the Para position to the group we just added is protonated, giving it a positive charge. A water molecule is then used to nucleophilically substitute for the OHCOCH3 group. The HOH is then deprotonated. A radical reaction is then performed to brominate the CH3 in the para position to the substitution we just did. This is done by the B2, breaking apart from the UV light and bonding with a hydrogen from the CH3 group. This leaves the no CH2 and Br as radicals and they form a bond. The newly brominated compound is reacted with tert-butylamine. This begins with the nucleophilic substitution of the tert-butylamine for the bromine. The lone pair of electrons on the nitrogen attacks the CH2Br and simultaneously the bond on the bromine is broken. The NH2 has a positive charge so it is deprotonated by the bromine creating HBr. Our compound is now reacted with LiAlH4. To begind a hydronium ion is taken from the AlH4 and attached to the carbon connected to the double bonded oxygen. This breaks one of the bonds causing the oxygen to become negatively charged. The negatively charged oxygen is then protonated, and that gives us our final product of Ventolin HFA, also known as Sulbutamol.

Explanation / Answer

Hydroelectricity is the term referring to electricity generated by hydropower; the production of electrical power through the use of the gravitational force of falling or flowing water.

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