d r e a m y
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Hi, for this question, I got as far as:
-butylamine (isomer A in a straight chain) reacts with nitrous acid to give effervescence
-at 5C a primary aromatic amine reacts with nitrous acid to give a diazonium compound
-this can react with a phenol in alkaline solution to give an orange dye

Im not sure what happens at 20C or what happens with aliphatic amines. Could someone help?
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Davies Chemistry
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(Original post by d r e a m y)
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Hi, for this question, I got as far as:
-butylamine (isomer A in a straight chain) reacts with nitrous acid to give effervescence
-at 5C a primary aromatic amine reacts with nitrous acid to give a diazonium compound
-this can react with a phenol in alkaline solution to give an orange dye

Im not sure what happens at 20C or what happens with aliphatic amines. Could someone help?
The diazonium ion (R-N2+) is very unstable and will react with water in the HNO2 solution to give the alcohol (or phenol if R is a benzene ring)

The benzene diazonium ion is a lot more stable than the aliphatic diazonium ion (e.g CH3CH2CH2CH2N2+) because the positive charge can be delocalised over the benzene ring. This means the benzene diazonium ion in solution is stable as long as the temp remains around 5 oC. If the temp rises as high as 200C it will react with water to give N2 gas and phenol.

The aliphatic diazonium ion will react with H2O to give the alcohol and N2 even at 5 oC

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d r e a m y
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(Original post by Davies Chemistry)
The diazonium ion (R-N2+) is very unstable and will react with water in the HNO2 solution to give the alcohol (or phenol if R is a benzene ring)

The benzene diazonium ion is a lot more stable than the aliphatic diazonium ion (e.g CH3CH2CH2CH2N2+) because the positive charge can be delocalised over the benzene ring. This means the benzene diazonium ion in solution is stable as long as the temp remains around 5 oC. If the temp rises as high as 200C it will react with water to give N2 gas and phenol.

The aliphatic diazonium ion will react with H2O to give the alcohol and N2 even at 5 oC

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