Saturated Acyclic Hydrocarbons
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1 Kevin Burgess, December 4, Saturated Acyclic ydrocarbons A. Intro-duck-shun
2 Kevin Burgess, December 4, B. Conformations Of Acyclic ydrocarbons Ethane θ = 60 θ = 0 shown slightly offset but direct allignment is assumed staggered eclipsed staggered eclipsed staggered eclipsed
3 Kevin Burgess, December 4, The staggered ethane conformer is more stable called torsional strain. θ e s e s e s e Energy kj mol -1
4 Kevin Burgess, December 4, indicate destabilizing interactions stabilizing interactions between empty and filled orbitals in staggered conformations. if both the highest occupied molecular orbital (OMO) and lowest unoccupied molecular orbital are filled, this is slightly destabilizing. contributes 2 e empty one donates 0 e. σ repulsive σ σ attractive σ* torsional strain add electrons to the diagrams below and indicate bond orders: σ σ σ σ* bond order = _1/2 bond order = _1 Propane θ = 60 θ = 0 C 3 C 3 shown slightly offset but direct allignment is assumed staggered eclipsed
5 Kevin Burgess, December 4, use most stable conformer as 0 Relative Energy kj mol C 3 e 60 C 3 s 120 C 3 e θ 180 C 3 s C e C s C e eclipsed
6 Kevin Burgess, December 4, Butane very low high low very high low high very low C 3 C 3 3 C C 3 3 C C 3 C 3 C 3 a pe g fe
7 Kevin Burgess, December 4, Relative Energy kj mol C 3 C 3 pe 60 C 3 C 3 a C C pe θ C C 3 C 3 g C fe 300 C 3 C 3 C 3 g 360 C 3 pe
8 Kevin Burgess, December 4, C. Art In Organic Chemistry represents C 3, two bonds to an apex means it is a C 2, and three bonds to a branch point represent C. If there are four bonds to a central point, this means there are 0 hydrogen atoms on that carbon. propane pentane nonane 3 C 2 C C3 3 C 2 C C2 2 C C3 3 C 2 C C2 2 C C2 2 C C2 2 C C3 ethane butane decane 3 C C 3 3 C 2 C C2 C 3 3 C 2 C C2 2 C C2 2 C C2 2 C C2 C 3 hexane heptane octane 3 C 2 C C2 2 C C2 C 3 3 C 2 C C2 2 C C2 2 C C3 3 C 2 C C2 2 C C2 2 C C2 C 3
9 Kevin Burgess, December 4, sp 3 hybridized carbons are 109. has 4 bonds to other atoms. structures always have this number never have five or more atoms attached to them. sp 3 because they have 4 atoms attached. tetrahedral shape about 109 2,2-dimethylpentane 2,2-dimethylpropane 2,2-dimethylbutane 3 C C C C C C C3 2 C 3 3 C C C C 3 C 2 C(C 3 ) 2 C 3 3 C 3
10 Kevin Burgess, December 4, octane heptane 2-methylhexane methylpropane 2-methylbutane 2,7-dimethylnonane Cl F 3-methylpentane 2-chlorohexane 3-fluoroheptane Br I 2,3-dimethylpentane 3-bromohexane 1-iododecanane Cl Br Cl C 3 C 2 C 2 C 2 C 3 C 3 C 2 CClC 2 C 3 BrC 2 C(C 3 )CClC 2 C 3
11 Kevin Burgess, December 4,
12 Kevin Burgess, December 4, Three Dimensional Diagrams Of Organic Molecules... the C 3 hydrogen... both hydrogens on C 3... the on unique C
13 1 Kevin Burgess, December 4, Alkyl Fragments is called a methyl. that have C 2 connected to thine is the name given to C fragments. is called a methyl. A quaternary C has 0 hydrogen atoms attached. 6 7 O C1, C5, C6, C7, C8 methyl C2 quarternary C3 methine C4 methylene C1, C7, C8, C9, C10 methyl C2, C3, C5 methylene C4 = methine C6 = quarternary C1, C7 methyl C2, C3, C6 methylene C4 = methine ie substituted C 3, C 3 C 2, Et (circle all correct). cannot be isolated is not a discrete compound, is a molecular fragment. 2 types of hydrogen atoms different outcomes. C 2 C 2, EtC 2, n Pr (circle all correct). as i Pr, (C 3 ) 2C (circle all correct propane n-propyl butane n-butyl 3 types of hydrogen atoms gives a normal butyl group as C 2 C 2 C 2, n PrC 2, C 3 C 2 C 2 C 2 a iso- butyl group that can be represented as i PrC 2, (C 3 ) 2C ( isomer of butane: it has 2 an i Bu group. something, ie a t Bu group.
14 Kevin Burgess, December 4, n-butyl tert-butyl sec-butyl iso-butyl I I Cl Br C 3 Br 3 C C 3 2 C I C3 3 C C C C3 Br Cl C 3 C 2 C C3 n PrI i BuI i PrCl s BuBr Br t BuI s BuBr i BuCl O O O O O t BuO n BuO i PrO s BuO EtO
15 Kevin Burgess, December 4, O O O O O t BuO EtOEt i PrO i Pr t BuO i Pr O an anesthetic N N N 2 N N 2 t BuN Et i PrN t 3 N 2 BuNEt N 2 S S S S S s BuS EtS t Bu i PrSEt i BuS 2 S
16 Kevin Burgess, December 4, O S N N O n Pr S n Bu i PrNEt i BuN 2 alcohol thioether amine amine name functional groups as alcohol, amine, ether, or thioether on the dashed lines D. Conclusion These are zig-zag conformations. pentane hexane heptane decane can be
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