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Chapter 14: Q.21558-14-68P (page 567)

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

Short Answer

Expert verified

Answer

The structure of Q is as follows:

Step by step solution

01

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.

02

Analyzing data

Given data

Chemical formula =C5H9CIO2

Degree of unsaturation (1HD)=((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)=((2×5+2)-(9+1))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,
03

Proposing the structure

Structure of Q

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