Answer
64.8k+ views
Hint: Nitroalkanes can be obtained by treating alkyl halides with silver nitrate in alcoholic solution. Hydrolysis of $\alpha - $nitro alkene can produce nitromethane.
Complete step by step solution:
When $\alpha-$ chloro sodium acetate is treated with silver nitrate, the chlorine gets replaced by the nitro group and $\alpha - $nitro sodium acetate is formed, which undergoes hydrolysis to give nitro methane and sodium bicarbonate as a by-product.
This reaction is a nucleophilic substitution reaction. Since silver nitrite is predominantly covalent, only nitrogen pairs are available for bond formation. Hence, on adding $AgN{O_2}$, the attack of $NO_2^- $ takes place mainly through nitrogen and a nitroalkane is obtained as the major product.
![](https://www.vedantu.com/question-sets/24eb8171-11e0-4479-aaac-fded7d7d17983846668700401881914.png)
$\alpha - $nitro isobutylene undergoes hydrolysis in an acidic medium to give nitromethane and acetone.
![](https://www.vedantu.com/question-sets/3b1555c2-4957-441a-bc26-a4744f9ab7763049998228849769721.png)
Note: When $\alpha - $ chloro sodium acetate is treated with silver nitrate, some alkyl nitrate is also formed ($20-30\% $) in the reaction along with nitroalkane. This is because$NO_2^-$ ion is an ambident nucleophile and can attack the alkyl halide through nitrogen as well as through oxygen. If $\alpha -$ chloro sodium acetate is treated with $NaN{O_2}$ or $KN{O_2}$ in place of $AgN{O_2}$, the main product will be alkyl nitrite. Nitroalkenes do not undergo hydrolysis in the basic medium to form nitromethane.
Complete step by step solution:
When $\alpha-$ chloro sodium acetate is treated with silver nitrate, the chlorine gets replaced by the nitro group and $\alpha - $nitro sodium acetate is formed, which undergoes hydrolysis to give nitro methane and sodium bicarbonate as a by-product.
This reaction is a nucleophilic substitution reaction. Since silver nitrite is predominantly covalent, only nitrogen pairs are available for bond formation. Hence, on adding $AgN{O_2}$, the attack of $NO_2^- $ takes place mainly through nitrogen and a nitroalkane is obtained as the major product.
![](https://www.vedantu.com/question-sets/24eb8171-11e0-4479-aaac-fded7d7d17983846668700401881914.png)
$\alpha - $nitro isobutylene undergoes hydrolysis in an acidic medium to give nitromethane and acetone.
![](https://www.vedantu.com/question-sets/3b1555c2-4957-441a-bc26-a4744f9ab7763049998228849769721.png)
Note: When $\alpha - $ chloro sodium acetate is treated with silver nitrate, some alkyl nitrate is also formed ($20-30\% $) in the reaction along with nitroalkane. This is because$NO_2^-$ ion is an ambident nucleophile and can attack the alkyl halide through nitrogen as well as through oxygen. If $\alpha -$ chloro sodium acetate is treated with $NaN{O_2}$ or $KN{O_2}$ in place of $AgN{O_2}$, the main product will be alkyl nitrite. Nitroalkenes do not undergo hydrolysis in the basic medium to form nitromethane.
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