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1、Chapter 3 Alkenes and AlkynesAlkenesNomenclatureStructurePreparationReactionsChapter 3ALKENE COMMON NAMESEthylenePropyleneIsobutyleneIUPAC NAMESethaneethene(1) Find the longest carbon chain that contains the double bond, and name the compound using the suffix-ene. (2) The position of double or tripl
2、e bond in the base chain must be indicated using the lowest possible numbers. (3) The entire compound is named by first listing the substituents in alphabetical order.Next the position of the double bond is indicated, followed by the name of the parent carbon chain.(4) If more than one double bond i
3、s present, give the position of each and use one of suffixes diene, triene, and so on.What is the name of this compound?3-methyl-1-butene6-bromo-3-propyl-1-hexene1-Methylcyclohexene2-methyl-1,3-butadiene-ene-ol3-methyl-4-hexen-1-olPolyethyleneSamples of polyethylenePolypropyleneWhat is the name of t
4、his compound?1,3-butadieneisopreneisopreneRubberVitamine AVINYL GROUPCH2CHCH2CH Clvinyl chloridePVC, “vinyl”CH2CHCH2Allyl GroupCH2CHCH2OHAllyl AlcoholElectron Density Map EthyleneStereoisomersCISTRANSCis-2-buteneTrans-2-buteneStereo ViewTRANS CIS ?ROTATION HINDEREDBreak pi bondClC = CHBrFIs this cis
5、 or trans? E-Z NomenclatureZ-configuration: high-priority group on the same side of the double bond. E - Z Cahn-Ingold-Prelog Priority Rules1. Assign priority based on atomic numberSEQUENCE RULE : Rule 2. If a decision cant be reached by ranking the first atoms in the substituents, look at the secon
6、d, third, or fourth atoms away from the double-bond carbons until the first difference is found.Rule3. Multiple-bonded atoms are equivalent to the same number of single-bonded atoms.C = CClHBrFhigherlowerhigherlowerZZusammen (together)C = CClHFBrhigherlowerhigherlowerEEntegegen (opposite)C = CBrClCH
7、3HIs this E or Z?ZC = CBrClCH3CH2CH3Is this E or Z? E If 2 atoms the same look at next one.C = CBrClCH2OHCH2CH3Is this E or Z?ZC = CBrClCH2OHCH=OEcount twiceQuestion: (CH3)3C- and-CH2Cl, which has the priority?C = CCH3HHCH2CH3Is this E or Z?E or transC = CCH3HCH3CH2CH3Is this E or Z?E or CIS(E)-6-Me
8、thyl-3-propyl-2-octeneHeat of Combustion2717 KJ/Mole2710 KJ/Mole2707 KJ/MoleAlkyl groups stabilize carbon-carbon double bondsAn inductive effect: is simply the shifting of electrons in a bond in response to the electronegativity of nearby atoms.When speaking of an atoms ability to polarize a bond, we often use the term inductive effect.Electron-drawing group: -NO2 -CN COOH -F-Cl -Br -I -OH -C6H5 -CH=CH2 -H - I Electron-donating group: O- -COO- -C(CH3) 3-CH(CH3) 2-CH2CH3-CH3-H +IReviewAlkenesCommon NamesIUPAC NamesStructureBondingSequence rulesCis-Trans isomerismInductive effect
