Constitutional isomer of xylene should be identified to undergo a Birch reduction which produces a compound that should exhibit five signals in its 13 C NMR spectrum Concept introduction: The carbon atoms of aromatic rings typically produce signals in the range of 100-150ppm in 13 C NMR spectrum. The number of signals is very helpful in determining the specific substitution for substituted aromatic 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 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, Problem 50PP

Interpretation Introduction

Interpretation: Constitutional isomer of xylene should be identified to undergo a Birch reduction which produces a compound that should exhibit five signals in its 13C NMR spectrum

Concept introduction:

The carbon atoms of aromatic rings typically produce signals in the range of 100-150ppm in 13C NMR spectrum. The number of signals is very helpful in determining the specific substitution for substituted aromatic 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

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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