Alkanes Flashcards
Alkanes
CnH2n+2
Acyclic
Cyclic
Cyclic Alkanes
Ring structure
CnH2n
Cyclopropane-triangle
Cyclobutane- square
Cyclopentane-pentagon
Cyclohexane- hexagon
Acyclic Alkanes
Straight chain
Branched chain
CnH2n+2
Nomenclature
- Prefix
- Parent
- Suffix
Prefix
Substituents
Parent
Longest continuous carbon chain bearing principal functional group
Suffix
Principal functional group
Isomerism
Alkanes with 4 or more carbons exhibit structural isomerism due to branching of the hydrocarbon chains.
Physical properties
- Increasing MP/BP
- Increasing Density
- Not soluble
- Increasing viscosity
Increasing MP/BP
With increasing number of carbon, increasing Mr hence increasing electron cloud size.
Branched chain has lower MP/BP than straight chain due to lesser surface area of contact. Increasing degree of branching decreasing MP/BP
Increasing density
Increasing Mr down homologous series stronger id-id bringing alkane molecules closer together occupying smaller volume. Larger mass/smaller volume leads to increasing density down series (str8 chain)
density decreases with greater degree of branching
Not soluble
Alkanes are non polar molecules hence insoluble in polar solvents but soluble in non-polar solvents
Increasing viscosity
Increasing Mr as strength of id id increases down group increasing viscosity
Chemical properties
Reactivity
Combustion
Free radical substitution
Reactivity
generally unreactive (inert)
- due to non polar C-H bonds as C and H have similar electronegativities
- C-C and C-H bonds are strong
alkane do not have electron rich/poor centres to attract reactive charged species
Combustion
Alkanes (hydrocarbons) react with excess O2 to produce CO2 and H2O
if O2 supply limited incomplete combustion resulting in the formation of CO and/or soot-C and H2O
CxHy+ x+y/4O2 —–> xCO2 +y/2 H2O
Free radical substitution
Alkanes react with halogens such as Cl2 or Br2 in presence of UV light or high temperatures to prod. halogenoalkenes involving free radicals
a substitution reaction one or more of H atoms replaced by halogen atoms
Free radical mechanism
Initiation
Propagation
Termination
Initiation
Bond in Halogen molecule cleaved homolytically to produce 2 free halogen radicals in the presence of UV light/heat
Cl—–Cl (half arrow pointing from bond to each carbon)—-> 2Cl·
energy from UV sufficient to over Cl-Cl but not C-H hence bond in halogen molecule broken preferentially
Propagation
Halogen radicals undergo chain reaction (a repeated sequence of…)
e.g. 1Cl·+ CH4—–>CH3 + HCl
2. ·CH3 +Cl2 ——> Cl·+ CH3Cl
free Halogen radical used and regenerated and chain rxn continuous. Halogen radical behaves as a catalyst
Termination
Involves 2 rctive free radicals combine forming stable inert substance. Free radicals consumed
Any two
e. g. 1. 2Cl·—->Cl2
2. ·CH3+·CH3—->CH3CH3
3. ·CH3 + Cl· —–> CH3Cl
Poly substitution
multiple repetition of propagation steps according to how many halogen atoms substitute the H atoms in alkane
Di substitution- 2 pairs
Tri substitution - 3 pairs
Minimising multiple substitutions
Excess alkane/limited halogen molecule
monosubstituted alkane predominates greater chance for ·Cl collide with alkane than monosubstituted alkane in propagation
Reactivity of halogens with alkanes
increases increases in the order X-X bond energies
F2 (explosive)
Cl2/Br2 (250C-400C in UV light)
I (least reactive)