Halogen Alkane
General Formula of Alkene: CnH2n+1 X, where n=1,2,3,4,5,6,7,8,9,10 and X is the halogen.
![](https://static.wixstatic.com/media/8cfa88_cf978729ef8a4e4daf0dbfcb8b67a822~mv2.png/v1/fill/w_980,h_505,al_c,q_90,usm_0.66_1.00_0.01,enc_auto/8cfa88_cf978729ef8a4e4daf0dbfcb8b67a822~mv2.png)
Halogenoalkanes undergo nucleophilic substitution reactions.
Halogenoalkanes can be classified into three types:
1. Primary halogenoalkanes - Halogenoalkanes that have the halogen bonded to a carbon that has two hydrogens bonded to it.
![](https://static.wixstatic.com/media/8cfa88_2178d2e6853a4ab19b0009fae2ba22b5~mv2.png/v1/fill/w_438,h_281,al_c,q_85,enc_auto/8cfa88_2178d2e6853a4ab19b0009fae2ba22b5~mv2.png)
2. Secondary halogenoalkanes - Halogenoalkanes that have the halogen bonded to a carbon which has one hydrogen bonded to it.
![](https://static.wixstatic.com/media/8cfa88_9f376a780aab496eac86ddbcb7c48afa~mv2.png/v1/fill/w_980,h_559,al_c,q_90,usm_0.66_1.00_0.01,enc_auto/8cfa88_9f376a780aab496eac86ddbcb7c48afa~mv2.png)
3. Tertiary halogenoalkanes - Halogenoalkanes that have the halogen bonded to a carbon that has no hydrogen bonded to it.
![](https://static.wixstatic.com/media/8cfa88_f34122fcc99e41b0bd88b51eb02c76a8~mv2.png/v1/fill/w_980,h_458,al_c,q_90,usm_0.66_1.00_0.01,enc_auto/8cfa88_f34122fcc99e41b0bd88b51eb02c76a8~mv2.png)
There are two mechanisms of Nucleophilic substitution reaction:
(a) SN1
(a) SN2
Primary halogenoalkanes undergo SN1 reaction mechanism.
Tertiary halogenoalkanes undergo SN2 reaction mechanism.
Secondary halogenoalkanes can undergo both SN1 and SN2 reaction mechanism.
Reactions of halogenoalkanes:
1. Halogenoalknes can react with aqueous sodium hydroxide to make alcohol and sodium chloride.
For this reaction, the reactants are needed to be heated under reflux
![](https://static.wixstatic.com/media/8cfa88_fd604aab39074fe38bd9f87a4af24c39~mv2.png/v1/fill/w_907,h_240,al_c,q_85,enc_auto/8cfa88_fd604aab39074fe38bd9f87a4af24c39~mv2.png)
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2. Halogenoalknes can react with aqueous sodium hydroxide in the presence of an alcohol to make alkene.
These reactions are called elimination reactions.
![](https://static.wixstatic.com/media/8cfa88_0693a8622b914ea6b5579b509a47b1ad~mv2.png/v1/fill/w_781,h_114,al_c,q_85,enc_auto/8cfa88_0693a8622b914ea6b5579b509a47b1ad~mv2.png)
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3. Halogenoalkanes react with excess ammonia in ethanol to make amine.
High pressure is needed for this reaction.
![](https://static.wixstatic.com/media/8cfa88_97f7cbf2662e4ec994d4147d58e4ffff~mv2.png/v1/fill/w_631,h_219,al_c,q_85,enc_auto/8cfa88_97f7cbf2662e4ec994d4147d58e4ffff~mv2.png)
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**It is important to use excess ammonia otherwise a mixture of amines will be formed.
4. Halogenoalkanes react with potassium cyanide in ethanol to make nitrile.
For this reaction, the reactants are needed to be heated under reflux
![](https://static.wixstatic.com/media/8cfa88_cc1517e2262944218d3c0139e245924f~mv2.png/v1/fill/w_850,h_67,al_c,q_85,enc_auto/8cfa88_cc1517e2262944218d3c0139e245924f~mv2.png)
![](https://static.wixstatic.com/media/8cfa88_fcfbd871dfbe49f490635efda2a213f9~mv2.png/v1/fill/w_780,h_187,al_c,q_85,enc_auto/8cfa88_fcfbd871dfbe49f490635efda2a213f9~mv2.png)
Reaction Mechanisms
SN1
This is called a nucleophilic substitution reaction.
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