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Hydrocarbons CxHyCxHy Hydrides of Carbon
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Carbon has four valence electrons. Wants to form four bonds. Hydrogen has one valence electron and wants to form one bond Methane
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Ethane Propane Butane
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Methane CH 4 Ethane C 2 H 6 Propane C 3 H 8 Butane C 4 H 10
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Ethane Conformations Staggered Eclipsed
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0 60 120 180 240 300 360 Angle of Rotation, degrees 12 kJ Variation of Energy with Rotation of C-C bond in Ethane
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Butane C 4 H 10 n- 2-methylpropane or isobutane These two molecules are structural isomers. They differ in the way their atoms are connected They have different chemical and physical properties.
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2-methylpropane or isobutane
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n-hexane These structures represent different conformations of n-hexane, not isomers.
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n-hexane 2-methylpentane 3-methylpentane 4-methylpentane 2,3-dimethylbutane2,2-dimethylbutane
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These are the five isomers of hexane, C 6 H 14
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Methane becomes Methyl Ethane becomes Ethyl Propane becomes Propyl
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1MethaneMethyl 2EthaneEthyl 3PropanePropyl 4ButaneButyl 5PentanePentyl 6HexaneHexyl 7HeptaneHeptyl 8OctaneOctyl 9NonaneNonyl 10DecaneDecyl
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Find the longest chain7 carbons. It’s a heptane Number the atoms Add the substituents in alphabetic order 4-ethyl-2-methylheptane
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5 carbon chain. It’s a pentane 3 methyls so use the prefix - tri 2di- 3tri- 4tetra- 5penta- 6hexa- 2,2,4-trimethylpentane not 4,4,2-trimethylpentane
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9 carbon chain It’s a nonane 2 methyl groups and 1 ethyl group 4-ethyl-3,7-dimethylnonane not 6-ethyl-3,7-dimethylnonane
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hexane 2-methylpentane 3-methylpentane 2,3-dimethylbutane 2,2-dimethylbutane
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What is special about this compound? 3-methylhexane These two compounds are different. One Is left handed and the other is right handed. The two compounds are mirror images.
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Put your thumb toward you representing the hydrogen atom, the lightest group. Point your fingers toward the propyl group, the heaviest group. Curl your fingers toward the ethyl group, the second heaviest group. Left Handed or S Right Handed or R These molecules are Chiral. They have handedness.
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S-3-ethyl-2-methylhexane
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Molecular Formulas for Alkanes are all of the form C n H 2n+2 2,2,4-trimethylpentanen-octane n = 8 2n + 2 = 18 C 8 H 18
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Molecular Formulas for Alkenes are all of the form C n H 2n 2,4,4-trimethyl-2-pentene 1-octene n = 8 2n = 16 C 8 H 16
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cis-2-pentenetrans-2-pentene If an alkene has two identical substituents on the two different carbons, they can be named cis or trans. If the identical substituents are on the same side we call themolecule cis. If they are on opposite sides we call the molecule trans. The two compounds shown above are stereoisomers.
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If two substituents on one carbon are the same cis and trans do not apply But what do we do if all groups are different?
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Instead of cis or trans use E or Z Z means the two heaviest groups are on the same side of the double bond. E means the two heaviest groups are on different sides of the double bond. (E) - 3-methyl-3-heptene(Z) - 3-methyl-3-heptene
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cis-3,5-dimethyl-2-hexene (E)-2,4-dimethyl-3-hexene 2-ethyl-4-methyl-1-pentene
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Molecular Formulas for Alkynes are all of the form C n H 2n-2 1-octyne n = 8 2n - 2 = 14 C 8 H 14
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2-methyl-3-hexyne 3-ethyl-6-methyl-1-heptyne
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trans-2-pentenecyclopentane C 5 H 10
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Cycloalkanes C n H 2n cyclopropanecyclobutane cyclopentanecyclohexane
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Cyclopropane
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cis-1,2-dimethylcyclopropane trans-1,2-dimethylcyclopropane
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trans-1,2-dimethycyclobutane cis-1-ethyl-3-methylcyclobutane
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Cyclohexane Ideal angles are 120 degrees. Actual angles are 109.5 degrees, the tetrahedral angle
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Benzene
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1,3-dimethylbenzene 1,4-dimethylbenzene 1,2-dimethylbenzene methylbenzene toluene ortho metapara
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Draw all compounds of formula C 4 H 8 Draw all compounds of formula C 4 H 6 Draw all compounds of formula C 4 H 10
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