Please draw out structures and answer all the questions :) H5. (A) Finish the resonance forms of the sigma complexfor the electrophilic aromatic substitution ofbromobenzene where the electrophile lands para tothe bromine. You should get a total of four resonanceforms; the fourth one is something you haven't seenbut explains why halogens are ortho/para directors forthe second EAS.HEⓇ:Br:H R.D.S.Br&:Br:Three more(B) Could you get this fourth resonance form if theelectrophile (E) landed meta to the bromine?(C) Even though the halogens are ortho/para directorsthe EAS runs slower than the EAS of benzene. Sketchthe reaction coordinate diagram that shows therelative energies (i.e. stabilities) of the sigmacomplexes for para EAS, meta EAS and for the EASof benzene (i.e. reference). As an option, speculatewhy the EAS on a phenyl halide runs slower thanbenzene even though halogens are ortho / paradirectorsSigma complexes forEAS ofbromobenzenerelative to benzene

Answered: (A) Finish the resonance forms of the…

Chemistry

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ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

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Please draw out structures and answer all the questions :)

H
5. (A) Finish the resonance forms of the sigma complex
for the electrophilic aromatic substitution of
bromobenzene where the electrophile lands para to
the bromine. You should get a total of four resonance
forms; the fourth one is something you haven't seen
but explains why halogens are ortho/para directors for
the second EAS.
H
EⓇ
:Br:
H R.D.S.
Br
&
:Br:
Three more
(B) Could you get this fourth resonance form if the
electrophile (E) landed meta to the bromine?
(C) Even though the halogens are ortho/para directors
the EAS runs slower than the EAS of benzene. Sketch
the reaction coordinate diagram that shows the
relative energies (i.e. stabilities) of the sigma
complexes for para EAS, meta EAS and for the EAS
of benzene (i.e. reference). As an option, speculate
why the EAS on a phenyl halide runs slower than
benzene even though halogens are ortho / para
directors
Sigma complexes for
EAS of
bromobenzene
relative to benzene

Expert Solution

Step 1

An electrophile substitutes an atom that is attached to an aromatic ring in electrophilic aromatic substitution reactions, that are organic processes. Typically, in such reactions, an electrophile takes the place of a hydrogen atom from a benzene ring.

In these electrophilic aromatic substitution (EAS) reactions, there are different groups that directs the incoming electrophile in different position w.r.t. the substituents. Like electron releasing substituents like bromo(-Br), chloro(-Cl), methoxy(-OCH₃), methyl(-CH₃) etc. on the benzene ring directs the incoming electrophile to the ortho/para position w.r.t. the substituents.

Whereas, electron withdrawing group like nitro(-NO₂), ester(-COOR), etc. direct the incoming electrophile to meta position w.r.t. the substituents.

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