Distinction between Ethyl nitrite and Nitro ethane
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Test
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Ethyl nitrite (C2H5ONO)
(Alkyl nitrite, RONO)
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Nitro ethane (C2H5NO2)
(Nitro alkane, RNO2)
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Boiling point
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Low, 17°C
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Much higher, 115°C
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Reduction with metal and acid
(Sn/HCl) or with LiAlH4.
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Gives alcohol + hydroxyl amine or NH3.
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Gives corresponding primary amine.
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Action of NaOH (alkalies).
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Readily hydrolysed to give corresponding alcohol and sodium nitrite (decomposition).
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Not decomposed, i.e., alcohols are not produced. But it may form soluble sodium salt, because in presence of alkali the nitro form changes into aci form, which dissolves in alkalies to form sodium salt.
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Action of HNO2 (NaNO2+ HCl)
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No action with nitrous acid.
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Primary nitro alkanes forms nitrolic acid, which dissolve in alkali to give red solution.
Secondary nitro alkane yields pseudo-nitrol, which dissolves in alkali to give blue solution.
Tertiary nitro alkanes does not react with nitrous acid.
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