# Formation of Aniline from Chlorobenzene

My textbook says:

When chlorobenzene is treated with aqueous ammonia at 473K under a pressure of 60 atmospheres in presence of cuprous oxide or cuprous chloride, aniline is formed.

Notice the reaction given. It shows Cuprous chloride ($$\ce{Cu2Cl2}$$) as a by-product. The question is, if cuprous chloride is used for treating chlorobenzene initially, the whole equilibrium should shift backwards, that is, the formation of aniline shouldn't be favourable, because $$\ce{Cu2Cl2}$$ is formed in the process.

Is my textbook wrong here in giving the statement? Or am I missing something?

Your textbook's text is correct but the reaction image is incomplete. Reaction of chlorobenzene with ammonia in presence of both the cuprous chloride and cuprous oxide forms aniline but via two different reactions. Your textbook only mentions one of the reactions in the image.

In the reaction involving the oxide, cuprous oxide is a reactant and is consumed during the reaction whereas in the case of the second reaction, cuprous chloride acts as a catalyst and isn't used up during the reaction. The mention of the second reaction can be found in Industrial Organic Chemistry, Klaus Weissermel and Hans-Jurgen Arpe[1], where the following reaction is mentioned,

$$\ce{Ph-Cl + 2NH3 + CuCl -> Ph-NH2 + NH4Cl}$$

The same reaction can also be found on The chemical thesaurus reaction chemistry database[2].

References:

(1) Rose, J. Industrial Organic Chemistry Klaus Weissermel and Hans-Jurgen Arpe 3rd Edn. VCH, Weinheim, 1997 Xvii + 464 Pages. £70 ISBN 3-527-28838-4. Appl. Organomet. Chem. 1999, 13 (11), 857–858.

(2) Leach, M. R. The chemical thesaurus reaction chemistry database
http://www.chemthes.com/rxn_dp.php?id=3489 (accessed Jun 25, 2021).

• I had a look at a few of your edits, and there's nothing wrong with them per se, but you should avoid doing so many at once; it bumps everything to the front page and pushes actual new questions out of the way. This is especially so for formatting / visual edits, like making references smaller. It doesn't actually make a real difference to the post, so it's doubly not worth flooding the front page with. – orthocresol Jun 29 at 11:43
• @orthocresol Yes I agree I should have been more patient. I also noticed that they started clogging up the main page and so I stopped doing them a while ago. Will take care from next time. – Nisarg Bhavsar Jun 29 at 11:45
• Thanks. A good rule of thumb is just do 5 at a go, then give it a break, for a few hours or a day. – orthocresol Jun 29 at 11:46
• @orthocresol If 5 is the recommended number, than I overshot a lot! Sorry for all this hassle! ʕ ﹷ ᴥ ﹷʔ – Nisarg Bhavsar Jun 29 at 11:48