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SC CHEM 334 - substituted nomenclature

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Chem 334 1nd Edition Lecture 4 Outline of Last Lecture I. Aromatic compoundsOutline of Current Lecture II. Monosubstituted NomenclatureIII. Disubstituted NomenclatureIV. PAHV. PhenolsCurrent LectureMonosubstituted Nomenclature: CH3 Benzene Tuluene ethyl benzene Styrene Phenol Aniline Benzaldehyde benzoic acid anisolDisubstitutedWhen naming certain molecules, we use 1,2 or 1, 3 or 1,4 to describe the position of the attached groups. However, we can also name these positions using the prefixes ortho, meta, and para.Example: These notes represent a detailed interpretation of the professor’s lecture. GradeBuddy is best used as a supplement to your own notes, not as a substitute. NH2OHOOOHOH1,2 dimethyl benzene OR ortho-dimethyl benzene OR o-dimethyl benzene1,3 dimethyl benzene OR meta-dimethyl benzene OR m-dimethyl benzene1,4 dimethyl benzene OR para-dimethyl benzene OR p-dimethyl benzeneIf possible, use the common names of the molecules:3-bromotoluene or meta-bromotolueneBr Cl 2-chloroaniline or ortho-chloroanilineHowever, when there is no common name for the molecule, list the substituents in alphabetical order before “benzene”:1-chloro-4-ethyl benzene or para-chloro ethyl benzene 1-bromo-3-chlorobenzene or meta-bromo chloro benzene ClIf you have more than two substituents you obviously cannot use ortho, meta or para to describe location. Instead, specify location by number. Once again, use common name for the molecule wheneverpossible. NO24-chloro-2-nitrotolueneNH2ClBrCl2, 4,6-tribromophenol BrPolynuclear aromatic hydrocarbons(PAH):PAH’s are two or more fused benzene rings that share two carbons. The two rings are fused together by two adjacent carbons.The simplest version of PAH: Naphthalene AnthraceneLarge PAH’s are formed during combustion. These make up carcinogens, which industrial companies try to remove with cleaners. This is because taking in these carcinogens is very harmful to your body. When you take in a carcinogen like cigarette smoke, you start with benzopyrene which your liver enzymes oxidize to epoxide. This makes it difficult for your body to transcribe DNA, and consequently the DNA gets mutated.Phenols:Phenols are widely found in nature. They consist of an aromatic, six membered ring with an OH group attached. Phenol is H2O soluble, meaning that it kills cells. For this reason, phenols were used at the first surgery antiseptic. OHBrOHHBrAcidity of phenols:Phenols have different chemical properties than alcohols. The pka of alcohol is around 16. The pka of a phenol is much less, around 10. However, the only difference in structure between the two is the alternating double bonds in the ring of a phenol. The pka of the phenol is so much lower because of the stability of the anion. The negative charge on the molecule is shared between four atoms, unlike alcohol which has no


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SC CHEM 334 - substituted nomenclature

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