Annotate the following C and H-NMR and label the peaks of the following compounds and provide the structure

Annotate the following C and H-NMR and label the peaks of the following compounds and provide the structure:

2-methoxy-6-(p-tolyliminomethyl)-phenol:

The Correct Answer and Explanation is :

To annotate the C-NMR and H-NMR spectra of 2-methoxy-6-(p-tolyliminomethyl)-phenol, we first need to understand its structure. This compound consists of a phenol ring substituted with a methoxy group (–OCH₃) at position 2, an iminomethyl group (–CH₂=N–) at position 6, and a p-tolyl group (–C₆H₄-CH₃) attached to the imino group.

Structure of 2-methoxy-6-(p-tolyliminomethyl)-phenol:

• Phenol ring: A benzene ring with a hydroxyl group (-OH) at position 1.
• Methoxy group (-OCH₃) at position 2.
• Iminomethyl group (-CH₂=N-) at position 6 of the phenol ring.
• p-Tolyl group (-C₆H₄-CH₃) attached to the iminomethyl group.

C-NMR Spectrum:

The C-NMR spectrum provides the chemical environments of the carbon atoms in the compound.

1. Aromatic region (around 110–160 ppm):

• C-2: Methoxy group (-OCH₃) attached to C-2: Typically, this will appear around 55-60 ppm for the methoxy group carbon (–OCH₃).
• C-6: Attached to the iminomethyl group: This carbon resonates around 130–140 ppm (due to the electron-withdrawing effect of the imino group).
• Other aromatic carbons: The remaining carbons in the aromatic ring (C-3, C-4, C-5, C-7, C-8) will fall within the 110–140 ppm range.

1. Aliphatic region (around 40–60 ppm):

• Iminomethyl group (-CH₂=N): The carbon attached to the nitrogen in the iminomethyl group will appear around 40–50 ppm.
• p-Tolyl methyl group (–CH₃): The methyl group of the p-tolyl group will appear around 20–25 ppm.

H-NMR Spectrum:

The H-NMR spectrum provides the chemical shifts corresponding to protons in the compound.

1. Aromatic protons (around 6.5–8 ppm):

• Protons on the aromatic ring, especially on positions 3, 4, and 5, will resonate around 6.5–8 ppm.
• The pattern of these peaks will likely be multiplets due to the different couplings of the protons.

1. Methoxy proton (around 3.5–4.0 ppm):

• The proton of the methoxy group (-OCH₃) typically appears around 3.5–4.0 ppm.

1. Iminomethyl group (around 4.5–5.5 ppm):

• The –CH₂ group in the iminomethyl will appear as a doublet or triplet around 4.5–5.5 ppm, depending on the coupling constants.

1. p-Tolyl methyl protons (around 2.2–2.5 ppm):

• The methyl protons of the p-tolyl group will resonate around 2.2–2.5 ppm, showing a doublet due to the coupling with the adjacent aromatic protons.

Conclusion:

The structure of 2-methoxy-6-(p-tolyliminomethyl)-phenol consists of a methoxy group, an iminomethyl group, and a p-tolyl group, which influence the chemical shifts in both the C-NMR and H-NMR spectra. The annotation of the peaks will involve identifying the shifts corresponding to the aromatic, methoxy, iminomethyl, and p-tolyl groups. These spectra help to confirm the structure based on the expected chemical environments of the atoms in the molecule.