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UGA CHEM 2211 - Alkyl Substituents and Alkanes
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CHEM 2211 1st Edition Lecture 3 Outline of Last LectureI. Brᴓnsted-Lowry Acid Base TheoryII. Ka valueIII. Factors that affect KaIV. Conjugate Acids and BasesV. Resonance StructuresOutline of Current LectureI. Alkyl group formationII. Addition of Functional groupsIII. Naming of Iso-structuresIV. Naming of sec- and tert-butyl structureV. Naming AlkanesVocabularyAlkyl groupFunctional groupPrimary CarbonPropylIsopropylSecondary CarbonButylIsobutylSec-butylTert-butylTertiary CarbonAlkaneParent ChainCurrent LectureI. An Alkyl group is formed by removing one hydrogen from an Alkane.CH3—Methyl groupCH3CH2—Ethyl groupCH3CH2CH2—Propyl groupR— is used to denote a methyl groupII. Different functional groups can be added to an alkyl substituentR—OH an alcohol R—NH2an amineR—X an alkyl halide (X= F, Cl, Br, I)R—O—R an etherIII. There are two molecules with a three carbon chain: propyl and isopropylA. A propyl group is a group with a hydrogen removed from the primary carbon.i. Primary Carbon- a carbon bonded to only one other carbonCH3CH2CH3  CH3CH2CH2— Propane  a Propyl GroupB. An isopropyl group has a secondary carbon bonded to one hydrogen and to two CH3 groupsi. Secondary Carbon- a carbon bonded to two carbonsCH3CH2CH3  CH3CHCH3 Propane  an Isopropyl GroupC. EXAMPLEFigure 1 Propyl ChlorideFigure 2 Isopropyl ChlorideIV. There are four alkyl groups with four carbons: butyl, isobutyl, sec-butyl, and tert-butylA. While butyl and isobutyl follow the same rules as propyl and isopropyl above, sec-butyl and tert-butyl are different.i. Sec-butyl has a hydrogen removed from a secondary carbonii. Tert-butyl has a hydrogen removed from a tertiary carbon1. Tertiary Carbon- a carbon bonded to threeFigure 3 Butyl GroupFigure 4 Isobutyl GroupFigure 5 Sec-butyl GroupFigure 6 Tert-butyl GroupV. Naming AlkanesA. Rulesi. Determine the longest continual chain of carbons known as the parent chain4-methyloctane4-ethyloctaneii. Number the chain in the direction that give the substituent the lowest number possible1. REMEMBER only systematic names have numbers2-methylpentane NOT 4-methylpentane3-ethylhexane NOT 4-ethylhexaneiii. If more than one substituent is attached to the parent hydrocarbon, the chain is numbered in the direction that will produce the name containing the lowest of the possible numbers. Substituents are listed in alphabeticalorder, not numerical order (Bruice, 2014).5-ethyl-3-methyloctane NOT 4-ethyl-6-methyloctane1. The prefixes “di”, “tri”, tetra”, etc. indicate the number of identical substituents are on the parent chain.2, 4-dimethylhexaneiv. If the same number is obtained in both directions for differing substituents, then the group listed first receives the lowest number.2, 2, 4-trimethylpentanev. When the substituents receive the same number when numbered both ways, the substituent that is labeled first gets the lowest number.2-bromo-3-chlorobutane NOT 3-bromo-2-chlorobutanevi. In a highly branched compound where the substituent also has branched portions, the substituent’s name is in parenthesis and is accompanied by a number indicating a position on the substituent.4-(1-methylethyl)heptanevii. In the case that two hydrocarbon chains have the number of carbons choose the one with the most


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UGA CHEM 2211 - Alkyl Substituents and Alkanes

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