Chapter 22, Problem 73IP

Interpretation Introduction

Interpretation: The two possible structures of the compound C₅H₁₃N that exhibits three signals in its proton NMR spectrum and no signals above 3000cm⁻¹ in IR spectrum have to be drawn.

Concept introduction:

The arrangement of atoms that are bonded together determines its constitution and molecular formula of that particular compound.  This concept is referred as structural isomers or in more modern term constitutional isomers.  Each atom has a typical valency or valence which is defined as the ability of an atom to form a chemical bond with other atoms.  For example, carbon has four valence or tetravalent that means carbon has the capacity to form four bonds with other elements or other atoms.  Nitrogen atoms are trivalent whereas hydrogen atoms are monovalent in nature.

If a compound has N−H bond in its structure, it shows a signal above 3000cm⁻¹ in IR spectrum. In proton NMR, the signals are based on the arrangement of hydrogen atoms that are connected to carbon atoms.

To find: Draw the two possible structures of the compound C₅H₁₃N that exhibits three signals in its proton NMR spectrum and no signals above 3000cm⁻¹ in IR spectrum

Find the valency for carbon (C), hydrogen (H) and nitrogen (N) in C₅H₁₃N