Textbook Question
Predict the major products of the following reactions.
(d) p-xylene + Na (liquid NH3, CH3CH2OH)
(e)
19. Reactions of Aromatics: EAS and Beyond
Birch Reduction
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Predict the major product from the Birch Reduction
A
B
C
D
Verified step by step guidance1
Identify the reaction type: The Birch reduction is a reaction that reduces aromatic rings to non-conjugated dienes using alkali metals (such as sodium) in liquid ammonia with an alcohol (such as t-butanol) as a proton source.
Analyze the starting material: The given compound is a naphthalene derivative with a trifluoromethyl (CF3) group attached. The Birch reduction will affect the aromatic ring system.
Determine the regioselectivity: In Birch reduction, electron-withdrawing groups (like CF3) direct the reduction to occur at the positions ortho and para to the substituent, avoiding the position directly adjacent to the substituent.
Predict the product structure: The reduction will result in the formation of a non-conjugated diene. The double bonds will be placed in positions that are not directly adjacent to the CF3 group, typically resulting in a 1,4-cyclohexadiene structure.
Consider the options: Among the given options, identify the structure that matches the expected product of the Birch reduction, considering the placement of the double bonds relative to the CF3 group.
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