Nucleophilic substitution

The goal of this lab was to prepare methyl m-nitrobenzoate using electrophilic aromatic substitution. An example of electrophilic aromatic substitution is nitration where a hydrogen atom which is part of a aromatic ring is substituted by an electrophile. For benzene, aromaticity is a stabilizing feature. As such, instead of undergoing electrophilic additions, it undergoes electrophilic substitutions. The nitronium ion is the electrophile which gets attached to the electron rich aromatic…

The purpose of the experiment was to form ketones by electrophilic aromatic substitution through a Friedel-Crafts acylation reaction of an aromatic compound. In the synthesized Friedel-Craft acylation reaction mechanism, the double bond on the nucleophile anisole (methoxybenzene) attacks the acetyl electrophile. The acetyl compound is then bound to the anisole in the para position, which created the product p-methoxyacetophenone. Since anisole is an activator (electron donor), the acetyl could…

Abstract The primary goal for this laboratory experiment was to synthesize, purify, and identify p-nitroacetanilide using acetanilide as the starting material. To test for the purity and identification of our desired product, we gathered data from: Thin Layer Chromatography (TLC), Melting Point (MP) range, Infrared (IR) spectrum, Gas Chromatography Mass Spectroscopy (GC-MS), and Proton Nuclear Magnetic Resonance (1H NMR). TLC plate indicated the formation of our pure product due to the…

This experiment was performed in order to demonstrate the principles of nitration through electrophilic aromatic substitution. It also examined the effects of bromine on an aromatic ring, ortho-para vs. meso directing. The second experiment was performed to compare the reaction rates of electrophilic aromatic bromination with different arenes. Data and Results In the gas chromatogram, there are two large peaks. The first peak at 0.653 minutes with an area of 133,352 uV per second, 31.95% of…

Since the dawn of sending and receiving messages, people have had a need for keeping the information they send out to remain private and out of the hands of others. This need for security is the reason the field of cryptography was developed, from its early stages of moving letters around in words to the present use of computer programming to keep certain data safe. Cryptography is the reason we can securely use many day to day applications, but with all these developments come issues of…

Interaction of concentrated nitric acid and sulfuric acid generated nitronium ion which is electrophile. And methyl benzoate nitration is one of electrophilic aromatic substitution. Nitronium ion will reacts with protonated intermediate at the meta position. After NO2 substituted, it becomes arenium ion intermediate. Then, the remained product HSO4- will attack hydrogen then transfer the proton to methyl 3-benzoate. In the experiment, students placed around 12 drops of concentrated H2SO4 in…

concepts behind electrophilic aromatic substitution. As the term states, the experiments deal with the chemistry of six membered ring compounds and their transformations through electrophilic substitutions. This type of reaction transforms the aromatic compound by allowing various functional groups to be attached to it. The general process of this reaction is a hydrogen on an aromatic ring, most simply an arene, being replaced by an electrophile. The substitution sometimes requires the…

oxygen and nitrogen atoms. The combined electron-withdrawing resonance and inductive effect ensures that the negative charge on the nitrogen atom is effectively dispersed. Step 2: nucleophilic substitution In Section 3.6 Halogen Derivatives, it was mentioned that an alkyl halide can undergo nucleophilic substitution by heating with excess alcoholic ammonia to yield a primary amine. Excess ammonia is necessary if a high yield of the primary amine is required. If excess ammonia is not used,…

Example: SN2 Mechanism Involving Electrically Neutral Nucleophile Mechanism of Nucleophilic Substitution: SN1 Example: SN1 Mechanism Involving a Negatively Charged Nucleophile…

T. Heinze et. al. reported the synthesis of new 6-deoxy-6-pheylethylamino cellulose derivatives with DSamino 0.4-0.6 by nucleophilic displacement of cellulose tosylates (DSTos 0.74 and 1.29) with a racemic mixture of 1-phenylethylamine under homogeneous conditions, in DMF/H2O82, scheme 30. The optical properties of these deoxyamino cellulose derivatives was studied. A regioselective synthesis of 6-amino-6-deoxycellulose, 6-N-sulfonated, and 6-N-carboxymethylated deoxycellulose were…