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10.6 - Reaction Pathways

10.6 - Reaction Pathways

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Published by: IB Screwed on Jun 30, 2011
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10.6 - Reaction Pathways
The different reactions that are possible for organic compounds are explained in more detailin previous sections. Some are outlined in this section too. It is important to be able tomanipulate the reactions and create combinations that will produce the desired product.Remember that the IB will never ask you to deduce a reaction pathway that involves morethan two steps.
10.6.1 - Deduce reaction pathways given the starting materials and the productReactions of Alkanes
The general equation for the complete combustion of alkanes is:
 
However, if there is insufficient oxygen available, the alkanes undergo incompletecombustion to produce a mixture of CO
, CO and C. For example:
 
 
Alkanes will undergo substitution reactions with halogens if there is a mechanism present(such as UV light or heat). During these reactions, the halogens will form
free radicals
-these have no charge, but have an unpaired electron, making them highly reactive. Duringthe reaction, the halogen will undergo
homolytic fission
to make the radicals.
 
This reaction takes place in a few steps:
This is when the radicals are formed.
This step happens first because the bonds between the halogen molecules areweaker and have a lower enthalpy than the C-H or C-C bonds.
In this step, the radicals are used, and new radicals are formed.
 
In the second stage of propagation, the CH
radical reacts with the chlorine moleculeto make CH
 
The free radicals are removed by reacting together
   
The methane and chlorine radicals can also be removed:
    
The methane radicals may react together:
 
In reality, there will be a mixture of products
, depending on the concentration of thereactants. These products can then be separated using distillation processes.
 Alkane to Alcohol 
This reaction must take place in two steps. In the first step, UV light is used to createchlorine radicals, and the reaction continues to form a halogenoalkane.The second step is an S
2 reaction, with the OH
ion attacking the carbon-chlorine bond. Areactive intermediate is formed, which then loses the Cl
Formation of a Halogenoalkane
This is a substitution reaction using a free radical mechanism
 
Reactions of Halogenoalkanes
Formation of an Alcohol 
This is an S
2 substitution reaction
Formation of a Trihalogenoalkane from a Dihalogenoalkane
This is a substitution reaction using a free radical mechanism
  

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