Question

Question. Compound Q has molecular formula C₅H₉CIO₂. Deduce the structure of P from its ¹H and ¹³C -NMR spectra.

Short answer

Answer

The structure of Q is as follows:

Step-by-step solution

Molecular structure

The most accepted arrangement of atoms and elements within a compound to satisfy the barriers of energy and steric effects is the molecular structure of a compound.

Analyzing data

Given data

Chemical formula =C₅H₉CIO₂

Degree of unsaturation (1HD)$=\frac{\left(\right(2n+2)-x)}{2}$

where,

n = number of carbon atoms

x = (number of hydrogen atoms) + (number of halogen atoms) - (number of nitrogen atoms)

On substituting values,

The degree of unsaturation (1HD)$=\frac{\left(\right(2\times 5+2)-(9+1\left)\right)}{2}$

=1

The value of IHD suggests the presence of a pi-bond.

The five signals in¹³C -NMR suggests the presence of five different types of carbon atoms.

From the ¹H-NMR spectra,

• The quartet at 4.2 ppm attributes to 2H atoms corresponding to split of two methyl groups,
• The triplet at 1.3 ppm attributes to 3H atoms due to split of 2H’s atoms,
• The triplet at 2.8 ppm attributes to 2H atoms due to split of 2H’s atoms,
• The triplet at 3.7 ppm attributes to 2H atoms due to split of 2H’s atoms,

Proposing the structure

Structure of Q