18-1 aliphatic hydrocarbons - 國立交通大學開放式課...
TRANSCRIPT
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Chapter 18 Organic Chemistry IThe Hydrocarbons
18-1 Aliphatic Hydrocarbons
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18-1
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Hydrocarbons
CxHy Aliphatic hydrocarbon
Aromatic hydrocarbon
CH3CH2
CH2
CH2
CH2
CH3
CH2CH3
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Chemical
Name
Chemical
Formula
Structural
Formula
Line
Structure
Condensed
Structural
Formula
Hexane C6H14CH3CH2CH2CH2CH2CH3
or
CH3(CH2)4CH3
CH3CH2
CH2
CH2
CH2
CH3
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Line Structure
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Condensed Structural formula
CH3
CH
CH2
CH2
CH2
CH
CH2
CH3
CH3 CH3
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Structural formula
CH3(CH2)2C(CH3)2CH2C(CH3) 3 C4H10
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AlkanesMethane CH4
Ethane CH3CH3
Alkenes
Alkynes
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~ane cyclo ~ ane
Butane
Methylpropane
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~ane~ane~yl
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CH3-
CH3 CH2-
CH3 CH2CH2-
CH3 CH
CH3
CH2
CH3
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cyclo
1
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3-Ethyl-hexane
12
3
CH3C(CH3)2CH2CH31 2 3
2,2-Dimethyl-butane
4
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di-, tri-, tetra-, penta-, hexa-
2,2,3-Trimethyl-butane
1-Ethyl-2-methyl-cyclopentane
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1
Write the structural formula of5-ethyl-2,2-dimethyldecane
2,3,5-trimethyl-4propylheptane
2-ethyl-1,1-dimethylcyclohexane
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2Write the name of
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~ane ~ene
~ane ~yneC
eneyne
1-Pentyne
2-Pentene
1,4-Pentadiene
123
3 12
12
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C
1. functional group suffixes
2. double bonds3. triple bonds4.
prefixes
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Name the compoundsCH3CH=CHCH3(CH3)2CHCH(CH3)CHClCCH
Write the condensed structural formula for 5-methyl-1,3-hexadiene
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CxHy Isomers
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Structural Isomers?
CnH2n+2 CnH2n CnH2n-2
Draw structural formulas for all the isomeric alkanes of formula
C5H12 3 isomers
C3H6 2 isomers
C4H9Br 4 isomers
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Geometric Isomers?
Draw structural formulas for all the isomeric alkanes of formula
Write the structure formulas and name all the isomers of the alkenes
C4H8
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Optical Isomers?
Indicate which of the following molecules are chiral
CH2FCl
CHFClBr
CH3CH(OH) CH3CH3CH(OH) CH2CH3
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Isomers
Identify each of the following pairs as structural isomers, geometric isomers, or not isomers:
Butane and cyclobutane
Cyclopentane and pentene
andand
and
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Isomers?
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Which compound has the higher boiling point?CH3CH2CH2CH2CH3 or CH3CH2CH2CH3 CH3CH2CH2CH2CH3 or (CH3)2CHCH2CH3
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C-CC-HCnH2n+2 +H2SO4CnH2n+2 +HNO3CnH2n+2 + MnO4-
CH4+2O2CO2+2H2OH = -890 kJ
CH4+Cl2CH3Cl+HClH = -105 kJ
(kJ/mol)
C-C 348
C-H 412
H-Cl 431
Cl-Cl 242
I-I 151
C-Cl 338
O=O 496
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ClCClCHClClClCHClClCHClClClCHClCHCl
molkJmolkJClClClmolkJClClCHCHClmolkJCHHClCHClmolkJClClCl
gHClgClCHgClgCHheatlight
heatlight
5n Propagatio 4n Propagatio 3n Propagatio
/ 105H / 243H :n Terminatio
/ 109 H 2n Propagatio/ 4 H 1n Propagatio/ 242H Initial
)()()()(
43
322
223
2
332
34
or 2
3or
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EX 18.26
A branched hydrocarbon C6H14 reacts with chlorine in the presence of light to give only two structural isomers with the formulas C6H13Cl.
Write the structure formulas of the hydrocarbon and the two isomeric products.
Do any of the products exist as optical isomers?
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Bond Enthalpies
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Elimination Reaction
dehydrohalogenation of haloalkanes
CH3CH3(g)Cr2O3
CH2 CH2 H2(g)(g) +
Br
CH3CH2O- Na
+
CH3CH2OHCH3CH2OH
NaBr+
at 70
+
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Electrophilic Addition CH2=CH2 + Br2 CH2Br-CH2Br
CH2=CH2 Br2 electrophile Lewis
Brd-
Brd+ Br+
Br
Br+
Br
Br
Br
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Ex 18.39
Two structural isomers can result when hydrogen bromide reacts with 2-pentene
Write their structural formulas
What name is given to this type of reaction?
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Ex 18.41
Write a balanced equation for the reaction of bromocyclohexane with sodium ethoxide in ethanol.
Draw structural formulas of the cyclic reactant and product.
What name is given to this type of reaction?
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OOO O
O
O
O
O
O
O
O
+ 3
Glycerol
Stearic acid
Tristearin, C57H110O6
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