DAT destroyer roadmap 2 question

[ScarletKnight24]

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Hi
I have a question about roadmap 2 for 2011 DAT destroyer on page 108.

Right where it started with a benzene it goes to the right and undergoes nitration. Then it reacts with 1)Sn,HCl and 2) OH- and became and amine (Do I just memorize this one? I never even saw this before a nitrobenzyl with Sn, HCl and OH, well at least in chads')

then the amine reacts with an acyl chloride to form an amide and this is where I got a bit confused.

When I saw the NH2 on the benzene ring, i think about it as an electron donating group on a benzene so if it reacts with an acyl chloride, shouldn't it undergo friedel craft acylation with the Nh2 directing the acyl chloride to be ortho or para while the Cl leaves? Is it not doing it because the catalyst isn't there?

sorry if it is NOT very clear.

 

[biomolecmed]

Whenever you have a Meta director, oh or an Nh2 on the benzene ring you cannot do friedel crafts because those groups take out the Lewis acid and the reaction cannot proceed. That is why you need to learn tthat in roadmaps. Hope this helps.

 

[ScarletKnight24]

Whenever you have a Meta director, oh or an Nh2 on the benzene ring you cannot do friedel crafts because those groups take out the Lewis acid and the reaction cannot proceed. That is why you need to learn tthat in roadmaps. Hope this helps.

Ok so whenever I have an electron withdrawing group on a benzene I will NEVER be able to do friedel craft acylation? Is this also true of alkylation?

What about sulfonation, nitration, chlorination, iodionation, and bromination? I would still be able to do these even if I have a meta director right?

thanks.

 

[ScarletKnight24]

Whenever you have a Meta director, oh or an Nh2 on the benzene ring you cannot do friedel crafts because those groups take out the Lewis acid and the reaction cannot proceed. That is why you need to learn tthat in roadmaps. Hope this helps.

WAIT I just realize something that you said wrong

Isn't NH2 an electron DONATING group/ortho/para director? The same with OH as well.

What the hell man lol

 

[ktran17]

Friedel-crafts reactions don't work with strong deactivators or activators.

examples inlucde, NO2 (deactivator) and NH2, NHR, or NR2 (strong activators)

reasoning:
1) strong deactivators draw so much electron density from the benzene and therefore prevent a reaction from occuring

2) strong activators are strong lewis bases and therefore have a lone pair that can react with the lewis acid needed for alkylation or acylation. This therefore prevents friedel-crafts.

 

[ScarletKnight24]

Friedel-crafts reactions don't work with strong deactivators or activators.

examples inlucde, NO2 (deactivator) and NH2, NHR, or NR2 (strong activators)

reasoning:
1) strong deactivators draw so much electron density from the benzene and therefore prevent a reaction from occuring

2) strong activators are strong lewis bases and therefore have a lone pair that can react with the lewis acid needed for alkylation or acylation. This therefore prevents friedel-crafts.

Ok so in order to do friedel craft alkylation or acylation, there must NOT be any donating or withdrawing group present on the ring?

 

[ktran17]

Strong deactivators and activators prevent friedel-crafts (acylation or alkylation) from occuring . however, the use of intermediate activators/deactivators are ok.

a really detailed explanation can be found on page 666 chapter 18 electrophilic aromatic of Organic chemistry by Janice Gorzynski Smith, second edition