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Question 51 of 66

Q.Draw the structure of urotropine and write its use.

Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2019Subjective· 2mImportance★★★★★
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Urotropine, (CH2)6N4(CH_2)_6N_4, is a cage-shaped condensation product of formaldehyde and ammonia, used medicinally as a urinary antiseptic and industrially in explosive (RDX) manufacture.

Formation: Urotropine (hexamethylenetetramine) is obtained by the condensation of six molecules of formaldehyde with four molecules of ammonia, with elimination of water:

6HCHO+4NH3→(CH2)6N4+6H2O6HCHO + 4NH_3 \rightarrow (CH_2)_6N_4 + 6H_2O

Structure: The molecule is a symmetrical, three-dimensional cage (an adamantane-type framework). The four nitrogen atoms occupy the four corners of an (imaginary) tetrahedron, and each of the six edges of this tetrahedron is spanned by one −CH2−-CH_2- (methylene) bridge connecting a pair of nitrogen atoms. As a result:

  • Each nitrogen atom is bonded to three different −CH2−-CH_2- groups (using its three N-C bonds, with its lone pair left free).
  • Each −CH2−-CH_2- group bridges (is bonded to) two different nitrogen atoms.

This can be represented in condensed form as (CH2)6N4(CH_2)_6N_4, a highly symmetric, cage-like, colourless crystalline solid, soluble in water.

Uses: …

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