From the given data of IR spectrum and 1 H NMR spectrum of the given molecular formula, structure and name of the compound should be given and the product should be predicted when it is treated with Birch condition. Concept introduction: In the IR spectrum, the signal just above 3000 cm -1 confirms the presence of aromatic ring Aromatic compound also produces a series of signals between 1450 and 1650 cm -1 in the IR spectrum In IR spectrum, a C=O bond will account for the signal at 1686 cm -1 In the 1 H NMR spectrum, the signals between 6.5 and 8ppm confirms the aromatic ring. The presence of a multiplet near 7 ppm is one of the best way to verify the aromatic ring The integration value of the multiplet near 7ppm indicates the extent of substitution. An integration of 5 indicates monosubstituted ring, an integration of 4 indicates disubsituted ring Birch reduction converts aromatic compound having benzoid ring in to a product 1, 4-cyclohexa diene. The product having hydrogen atoms attached on opposite end of the molecule Birch reduction is the reduction of aromatic rings with sodium, potassium or lithium and an alcohol in liquid ammonia. This is unlike catalytic hydrogenation When benzene with an electron donating group such as alkyl group is treated with Birch reduction, the carbon atom connected to the alkyl group is not reduced. Electron donating effect destabilizes the radical anion. When an electron withdrawing groups are used, different regiochemical outcome is observed. Electron withdrawing effect stabilizes the intermediate.

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Chapter 18.8, Problem 26CC

Interpretation Introduction

Interpretation: From the given data of IR spectrum and 1H NMR spectrum of the given molecular formula, structure and name of the compound should be given and the product should be predicted when it is treated with Birch condition.

Concept introduction:

In the IR spectrum, the signal just above 3000 cm-1 confirms the presence of aromatic ring

Aromatic compound also produces a series of signals between 1450 and 1650 cm-1 in the IR spectrum

In IR spectrum, a C=O bond will account for the signal at 1686 cm-1

In the 1H NMR spectrum, the signals between 6.5 and 8ppm confirms the aromatic ring. The presence of a multiplet near 7 ppm is one of the best way to verify the aromatic ring

The integration value of the multiplet near 7ppm indicates the extent of substitution. An integration of 5 indicates monosubstituted ring, an integration of 4 indicates disubsituted ring

Birch reduction converts aromatic compound having benzoid ring in to a product 1, 4-cyclohexa diene. The product having hydrogen atoms attached on opposite end of the molecule

Birch reduction is the reduction of aromatic rings with sodium, potassium or lithium and an alcohol in liquid ammonia. This is unlike catalytic hydrogenation

When benzene with an electron donating group such as alkyl group is treated with Birch reduction, the carbon atom connected to the alkyl group is not reduced. Electron donating effect destabilizes the radical anion.

When an electron withdrawing groups are used, different regiochemical outcome is observed. Electron withdrawing effect stabilizes the intermediate.

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