Alkanes-1 - Alkanes ALKANES (a family of hydrocarbons)...

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Alkanes
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ALKANES (a “family” of hydrocarbons) C n H 2n+2 CH 4 C 2 H 6 C 3 H 8 C 4 H 10 etc. C 2 H 6 ethane H H H—C—C—H H H
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sp 3 , bond angles = 109.5 o σ-bonds (sigma) rotation about C--C ( conformations ) representation: “andiron” or “sawhorse” C H H H H C H H
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“staggered” “eclipsed” torsional strain: deviation from staggered. Newman projections : H H H H H H H H H H H H H H H H H H H H H H H H
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rotation about C-C potential energy 3 Kcal The barrier to rotation about the carbon-carbon bond in ethane is 3 Kcal/mole. The rotation is ~ “free.”
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C 3 H 8 propane H C C C H H H H H H H projection formula CH 3 CH 2 CH 3 partially condensed formula
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staggered eclipsed H H H H H CH 3 CH 3 H H H H H rotation about C-C potential energy 3.4 Kcal
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C 4 H 10 butane(s) H C C C C H H H H H H H H H H C C C H H C H H H H H H H CH 3 CH 2 CH 2 CH 3 CH 3 CHCH 3 CH 3 projection partially condensed stick formulas
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Two isomers of butane C 4 H 10 : CH 3 CH 2 CH 2 CH 3 n -butane bp 0 o C mp –138 o C d 0.622 g/cc CH 3 CH 3 CHCH 3 isobutane bp -12 o C mp -159 o C d 0.604 g/cc
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Conformations about C2-C3 in n -butane: anti gauche CH 3 /H eclipsed CH 3 /CH 3 eclipsed H H CH 3 H H CH 3 CH 3 H H H 3 C H H H H H H H 3 C CH 3 CH 3 H H H H H 3 C
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CH 3 CH 3 H 3 C CH 3 H 3 C CH 3 H 3 C CH 3 anti gauche 3.4 Kcal 4.4-6.1 Kcal 0.8 Kcal potential energy rotation conformations about C2-C3 in n -butane:
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C 5 H 12 pentane(s) CH 3 CH 2 CH 2 CH 2 CH 3 n-pentane CH 3 CHCH 2 CH 3 isopentane CH 3 CCH 3 neopentane CH 3 CH 3 CH 3 these are common, or trivial, names where a prefix is used to idicate the structure.
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Alkane name isomers CH 4 methane 1 C 2 H 6 ethane 1 C 3 H 8 propane 1 C 4 H 10 butanes 2 C 5 H 12 pentanes 3 C 6 H 14 hexanes 5 C 7 H 16 heptanes 9 C 8 H 18 octanes 18 C 9 H 20 nonanes 35 C 10 H 22 decanes 75 ……. C 20 H 42 eicosanes 366,319 each new common name requires a new prefix…
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hexanes C 6 H 14 common names CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3 CHCH 2 CH 2 CH 3 n -hexane isohexane CH 3 CH 3 CH 3 CH 2 CHCH 2 CH 3 CH 3 CCH 2 CH 3 ????? CH 3 neohexane CH 3 CH 3 CHCHCH 3 CH 3 ????
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IUPAC nomenclature (Geneva, 1920) names of radicals (alkyl groups): CH 3 - methyl CH 3 Cl methyl chloride CH 3 OH methyl alcohol, etc. CH 3 CH 2 - ethyl CH 3 CH 2 CH 2 - n -propyl CH 3 CHCH 3 isopropyl |
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CH 3 CH 2 CH 2 CH 2 - n -butyl CH 3 CH 3 CH 2 CHCH 3 or CH 3 CH 2 CH- sec -butyl | CH 3 CH 3 CHCH 2 - isobutyl CH 3 CH 3 CCH 3 tert -butyl |
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CH 3 CH 2 CH 2 Br BrCH 2 CH 2 CH 3 CH 3 CH 2 CH 2 Br n -propyl bromide CH 3 CHCH 3 Br CH 3 CHBr CH 3 CH 3 CHBr CH 3 isopropyl bromide
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CH 3 CH 2 CH 2 CH 2 Cl CH 3 CH 2 CH 2 CH 2 Cl ClCH 2 CH 2 CH 2 CH 3 n -butyl chloride CH 3 CHCH 2 CH 3 Cl CH 3 CH 2 CHCH 3 Cl CH 3 CH 2 CH CH 3 Cl sec -butyl chloride
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isobutyl alcohol CH 3 CHCH 2 CH 3 OH CH 3 CH CH 3 CH 2 OH HO-CH 2 CHCH 3 CH 3 tert- butyl alcohol CH 3 CCH 3 CH 3 OH CH 3 C-OH CH 3 CH 3
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organic radicals:
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This note was uploaded on 11/02/2010 for the course CHEM 51LA 56555 taught by Professor Guan during the Spring '10 term at UC Irvine.

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Alkanes-1 - Alkanes ALKANES (a family of hydrocarbons)...

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