Q.Draw the structure of urotropine and write its use.
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Start your 14-day free trial to unlock the full solution →Urotropine, , 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:
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 (methylene) bridge connecting a pair of nitrogen atoms. As a result:
- Each nitrogen atom is bonded to three different groups (using its three N-C bonds, with its lone pair left free).
- Each group bridges (is bonded to) two different nitrogen atoms.
This can be represented in condensed form as , a highly symmetric, cage-like, colourless crystalline solid, soluble in water.
Uses: …
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