山东大学有机化学第八版烯烃和炔烃ppt.pdf

Organic Chemistryfor Students of Medicine and Biology 大学化学大学化学III和大学化学和大学化学III（（2））March 18, 2015Chapter 3 Alkenes and AlkynesMarch 10, 2015Nomenclature Structure Preparation Reactions(CnH2n)CH2H2CCH2CHCH3CH2CCH3CH3ALKENE COMMON NAMESEthylenePropyleneIsobutyleneCH2H2C etheneIUPAC NAMESethaneCH3CH3(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 triple 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 is present, give the position of each and use one of suffixes –diene, triene, and so on.CH2CHCHCH3CH3What is the name of this compound?3-methyl-1-buteneCH2BrCH2CH2CH2CHCHCH2CH3CH26-bromo-3-propyl-1-hexeneCH31-Methylcyclohexene2-methyl-1,3-butadieneF1234567-Fluoro-1, 3, 5-cycloheptatriene-ene -olCHCHCH2CH2OHCH3CHCH33-methyl-4-hexen-1-olCH3CH2CCHCH2CH2CH3CHCH2CH3CH34-ethyl-5-methyl-3-octene12345 678PolyethyleneCH2H2CCH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2H2CCH2H2CSamples of polyethyleneCH2=CHCH3PolypropyleneCH2-CH-CH2-CH-CH2-CH-CH2-CH-CH2-CH-CH3CH3CH3CH3CH3What is the name of this compound?1,3-butadieneisopreneCH2CCHH2CCH3isopreneRubberVitamine AOHVINYL GROUPCH2CHCH2CH Clvinyl chloridePVC, “vinyl”CH2CHCH2Allyl GroupCH2CHCH2OHAllyl Alcohol(2-propenyl)Electron Density Map EthyleneCCHHHH117.2oCCHHCH3CH3CC CH3HCH3HTRANSStereoisomersCISCis-2-buteneTrans-2-buteneStereo ViewStereo ViewTRANS CIS ?ROTATION HINDEREDBreak pi bondCl C = C HBrFIs this cis or trans?E-Z NomenclatureCC**CC**(Z)(E)Z-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 can’t be reached by ranking the first atoms in the substituents, look at the second, third, or fourth atoms away from the double-bond carbons until the first difference is found.CHHH C HNH2HRule3. Multiple-bonded atoms are equivalent to the same number of single-bonded atoms.COHRis equivalent toCOOHRC = CClHBrFhigherlowerhigherlowerZusammen (together)C = CClHFBrhigherlowerhigherlowerEntegegen (opposite)C = CBrClCH3HIs this E or Z?C = 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 CISCCCH3HCH2CH2CH2CH3CH2CHCH2CH3CH3(E)-6-Methyl-3-propyl-2-octeneCH3CH2CH=CH2Heat of CombustionCCCH3CH3HHCCCH3CH3HH+ 6O24H2O + 4 CO22717 KJ/Mole2710 KJ/Mole2707 KJ/MoleAlkyl groups stabilize carbon-carbon double bondsCCHHHCH3An inductive effect: is simply the shifting of electrons in a bond in response to the electronegativity of nearby atoms.CH3CH2CH2ClδδδδδδWhen speaking of an atom’s ability to polarize a bond, we often use the term inductive effect.δδδYC CH CXδδ+II=0-IElectron-withdrawing 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 +IReviewAlkenes Common Names IUPAC Names Structure Bonding Sequence rules Cis-Trans isomerism Inductive effect。