Using the resonance structures of the intermediates the observation that the electrophilic substitution of 3-phenylpropanenitrile occurs at ortho and para positions, but reaction with 3-phenylpropenenitrile occurs at the meta position is to be explained. Concept introduction: In aromatic electrophilic substitution reactions of monosubstituted benzenes, the resonance and inductive effects of the substituent group already present decides the orientation of the electrophile and reactivity. If both the effects reinforce each other and release electron towards the ring then the substituent group is an o- and p- director and activator. If on the other hand, if they reinforce and withdraw electrons from the ring then the substituent is meta orienting. If the two effects oppose each other then resonance effect decides the orientation and the inductive effect plays a role in determining the reactivity. To explain: Using the resonance structures of the intermediates, the observation that the electrophilic substitution of 3-phenylpropanenitrile occurs at ortho and para positions, but reaction with 3-phenylpropenenitrile occurs at the meta position is to be explained.

Question

Can the target compound at right be efficiently synthesized in good yield from the unsubstituted benzene at left? ? starting material target If so, draw a synthesis below. If no synthesis using reagents ALEKS recognizes is possible, check the box under the drawing area. Be sure you follow the standard ALEKS rules for submitting syntheses. + More... Note for advanced students: you may assume that you are using a large excess of benzene as your starting material. C :0 T Add/Remove step G

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Question

Chapter 16.SE, Problem 60AP

Interpretation Introduction

Interpretation:

Using the resonance structures of the intermediates the observation that the electrophilic substitution of 3-phenylpropanenitrile occurs at ortho and para positions, but reaction with 3-phenylpropenenitrile occurs at the meta position is to be explained.

Concept introduction:

In aromatic electrophilic substitution reactions of monosubstituted benzenes, the resonance and inductive effects of the substituent group already present decides the orientation of the electrophile and reactivity. If both the effects reinforce each other and release electron towards the ring then the substituent group is an o- and p- director and activator. If on the other hand, if they reinforce and withdraw electrons from the ring then the substituent is meta orienting. If the two effects oppose each other then resonance effect decides the orientation and the inductive effect plays a role in determining the reactivity.

To explain:

Using the resonance structures of the intermediates, the observation that the electrophilic substitution of 3-phenylpropanenitrile occurs at ortho and para positions, but reaction with 3-phenylpropenenitrile occurs at the meta position is to be explained.

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