a. What is the first step in the general mechanism for electrophilic aromatic su

Question

a. What is the first step in the general mechanism for electrophilic aromatic substitution? b. What is the driving force for losing a proton as the last step in electrophilic aromatic substitution? c. Why is sulfuric acid used in aromatic nitration? d. Consider the following reaction in which naphthalene is treated with sulfuric acid at low temperature and rationalize the outcome. e. Achille Umani-Ronchi and coworkers utilized an intramolecular Friedel-Crafts reaction to synthesize 1, 2, 3.4-tetrahydro-B-carbolines. Predict the most likely product from the following reaction.

Explanation / Answer

a) attacking of electron density from benzene ring on electrophile forms pi complex

b) by loosing H in last step compound retains its aromatic nature so it is driving force to loose proton.

c) because to generate NO2 electrophile from HNO3 it should act as base so we require stronger acid then HNO3 so we use H2SO4 to protonate HNO3

d) in major product during mechanism for stability of carbo cation. adjescent pi electrons are enough no need to disturb the aromatic nature of other ring.

in minor product to stabilize carbocation we should disturb aromatic nature of other ring.

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