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What are the possible product(s) to be obtained from the reaction of cyclobutyl amine with HNO 2 ???

What are the possible product(s) to be obtained from the reaction of cyclobutyl amine with HNO2???

Grade:12

1 Answers

chetan jangir
101 Points
4 years ago
Primary amines reacts with nitrous acid to form the corresponding primary alcohol with the evolution of nitrogen (gas). The reaction is as follows: RNH2 + HONO = ROH + N2 + H2O. However, cyclobutylamine reacts with nitrous acid to give a mixture of cyclobutyl alcohol (in accordance with the above reaction) and cyclopropyl carbinol (cyclopropylmethyl alcohol), the latter being formed by ring contraction. Formation of rearranged alcohol by ring expansion or ring contraction when a primary amine reacts with nitrous acid is known as Demjanov rearrangement. The reaction of cyclobutylamine with HNO2 is given below. C4H7NH2 + HNO2 = C4H7OH (cyclobutyl alcohol) +C3H5CH2OH (cyclopropylmethyl alcohol).

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