All the resonance forms for the sigma complexes that correspond to bromination of aniline at the ortho, meta and para positions are to be drawn. Concept introduction: Nitrogen atom of − NH 2 group in aniline contains a nonbonding pair of electrons. It is a strong activating group. It makes the aromatic ring more electron rich as compared to anisole. The sigma complex formed during the electrophilic substitution reaction is resonance stablised due to non bonding electrons of nitrogen. Aniline give ortho and para substituted products. To determine: All the resonance forms for the sigma complexes that correspond to bromination of aniline at the ortho, meta and para positions.

Question

1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.

Answer 1

Question

Chapter 17.6B, Problem 17.8P

Interpretation Introduction

Interpretation: All the resonance forms for the sigma complexes that correspond to bromination of aniline at the ortho, meta and para positions are to be drawn.

Concept introduction: Nitrogen atom of −NH2 group in aniline contains a nonbonding pair of electrons. It is a strong activating group. It makes the aromatic ring more electron rich as compared to anisole. The sigma complex formed during the electrophilic substitution reaction is resonance stablised due to non bonding electrons of nitrogen. Aniline give ortho and para substituted products.

To determine: All the resonance forms for the sigma complexes that correspond to bromination of aniline at the ortho, meta and para positions.

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