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Production of phenyl amines question

I'm confused about this question, I don't understand where the chlorine atom comes from.
benzene.jpg
For the first stage I wrote concentrated sulfuric and nitric acid, for the organic product I drew nitrobenzene.
For the second stage I wrote tin and concentrated hydrochloric acid under reflux and drew phenylammonium/ C6H6NH3 +
For the last bit I wrote you needed sodium hydroxide to accept the proton and produce the phenyl amine.
But as I said, where does the chlorine come into this? surely it would have had to be there to begin with unless chlorine Cl2 was added?
Original post by pineneedles
I'm confused about this question, I don't understand where the chlorine atom comes from.
benzene.jpg
For the first stage I wrote concentrated sulfuric and nitric acid, for the organic product I drew nitrobenzene.
For the second stage I wrote tin and concentrated hydrochloric acid under reflux and drew phenylammonium/ C6H6NH3 +
For the last bit I wrote you needed sodium hydroxide to accept the proton and produce the phenyl amine.
But as I said, where does the chlorine come into this? surely it would have had to be there to begin with unless chlorine Cl2 was added?


Clearly you are going to need to halogenate the benzene ring using aluminium chloride and chlorine (Friedel Crafts)
Original post by charco
Clearly you are going to need to halogenate the benzene ring using aluminium chloride and chlorine (Friedel Crafts)


Oh crappo, I forgot you needed a halogen carrier.
Why do you say and chlorine though? (Forget this question on second thought, I'm being a bit brainless this afternoon)
And would you just write add aluminium/iron chloride at the end, therefore?
(edited 8 years ago)
Original post by pineneedles
Oh crappo, I forgot you needed a halogen carrier.
Why do you say and chlorine though? (Forget this question on second thought, I'm being a bit brainless this afternoon)
And would you just write add aluminium/iron chloride at the end, therefore?


You write the reagents needed in the box which says chemicals.

Stage 1 - nitration
Stage 2 - reduction
Stage 3 - chlorination
Original post by charco
You write the reagents needed in the box which says chemicals.

Stage 1 - nitration
Stage 2 - reduction
Stage 3 - chlorination


Alright, I don't know why that confused me so much. I think I was trying to work out how the benzene ring became chlorinated through the process of nitration and reduction alone. Thankee sai :h:
Reply 5
BTW OCR accepted chlorination before the nitration and reduction. The old spec. had no expectation of knowledge of directing groups.
Original post by Pigster
BTW OCR accepted chlorination before the nitration and reduction. The old spec. had no expectation of knowledge of directing groups.


Ah, I see, thanks. :smile: What do you mean by directing groups?
Reply 7
If you attach things to a benzene ring then try a substitution reaction, the electrophile will attack differing positions on the ring.

Like I said, though, if you're a Y13 OCR A student, don't let it worry you as they won't examine/penalise lack of knowledge of it.

If you've got a Cambridge interview in January, I'd find out about it, though.
Original post by Pigster
If you attach things to a benzene ring then try a substitution reaction, the electrophile will attack differing positions on the ring.

Like I said, though, if you're a Y13 OCR A student, don't let it worry you as they won't examine/penalise lack of knowledge of it.

If you've got a Cambridge interview in January, I'd find out about it, though.


Oh, that's good. I do not have a Cambridge interview, thankfullly :tongue:
I remember my teacher talking about this briefly though, know I think about it.
Hi, I am re-doing my AS Chemistry OCR Controlled assessments, and I really need to do well.

Qual CA:
You will attempt to identify four unknown solutions;
You will investigate the effect of heat on three solid compounds.


What would I need to know/go over, in order to do well (i.e. precipitation reactions?)
PEASE REPLY ASAP AS IT IS URGENT...
Reply 10
I read the title of this thread as phenethylamine production. Was going to tell the OP expect the police to be kicking down your front door in the morning haha

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