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91Ó°ÊÓ

The proton NMR spectrum of a compound with formula C6H5NCl2is shown. The normal carbon-13 and DEPT experimental results are tabulated. The infrared spectrum shows peaks at 3432 and 3313 cm-1and a series of medium-sized peaks between 1618 and 1466 cm-1. Draw the structure of this compound.

Short Answer

Expert verified

1HNMRspectrum

13CNMRspectrum

Step by step solution

01

Determination of the structure

By observing the tabular form for C-13 NMR DEPT value the chemical shift values for the carbon are assigned and by observing the NMR spectrum, the values for hydrogens are assigned.

02

Proton NMR and C-13 Spectrum

The assignment of 1HNMR spectrum of the compound with molecular formula C6H5NCl2is as follows:

The key features of this1HNMR spectrum are:

  1. The amine protons at δ 4.35as a 2H, broad singlet as the protons are attached to the electronegative nitrogen atom and as these protons are exchangeable, the signal is broad.
  2. The protons give a doublet at δ 7.25as these are close to electronegative chlorine atoms and there is one adjacent proton.
  3. The aromatic protons give a peak around δ 6.70as this proton is ortho to the amine group.

1HNMR spectrum

The IR peaks at 3432 and 3313 cm−1corresponds to the N-H stretching frequency. The peaks in the range 1466-1618 cm−1corresponds to the aromatic ring.

For 13CNMR, CH2protons give the negative signal at DEPT-135 whereas CH3protons give the positive signal at DEPT-135. The assignment of 13Cpeaks is as shown:

13CNMR spectrum

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