1. Why do electron withdrawing groups on a benzene ring direct substitution to m

Question

1.  Why do electron withdrawing groups on a benzene ring direct substitution to mostly the meta position?

a) Meta positions are always more reactive  b) Intermediate from meta attack has 3 reasonably stable resonance structures while ortho or para attack yields one especially unstable resonance structure. c) The intermediate from meta attack has one especially stable and two reasonably stable resonance structures, while ortho/para attack yields three reasonably stable structures. d) The Intermediate from meta attack has two especially stable and one reasonably stable resonance structures, while ortho/para attack yields three reasonably stable resonance structures.  e) The intermediate from meta attack has two especially stable and one reasonably stable resonance structures, while ortho/para attack yields two reasonably stable and one especially unstable resonance structure.

2.  Let's say there is a phenol with a CF3 meta to the the hydroxyl group on the ring.  If cl2/alcl3 is used, what major product(s) will form.  

3.  Which of the following reactions can be used to alkylate benzene?

a) (CH3)2C=CH2/H+  b)  (CH3)3COH/H+  c)  (CH3)2CH2Cl/AlCl3  d) only a and b  e)  all of the above

4) The reaction of isobutyl bromide with benzene in the presence of AlCl3, yields ________ as the major product?

a) 2-Phenylbutane  b) n-butylbromide  c) isobutylbenzene d) t-butylbenzene

Explanation / Answer

1)   e) The intermediate from meta attack has two especially stable and one reasonably stable resonance structures, while ortho/para attack yields two reasonably stable and one especially unstable resonance structure.

2)

Cl meta to CF3 product forms

3) option C is correct

4) option C is correct

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