Sythesis Of 2

Sythesis Of 2-41
The addition of acid will require from an hour to an hour and a half.The stirring is then continued for half an hour longer without cooling; the mixture is allowed to stand over night in a separatory funnel; the lower layer of spent acid is drawn off; and the crude mononitrotoluene is weighed.The product, filtered off and dried at ordinary temperature, is equal to a good commercial sample of crude TNT. Davis, 148-149, 1941 2,4,6-trinitrotoluene is prepared by nitrating 2,4-dinitrotoluene with the nitrating mixture containing 83% of concentrated sulfuric acid and 14.5% of fuming nitric acid.

The addition of acid will require from an hour to an hour and a half.

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Slowly the temperature is raised to 110° C and keep at that temperature for 1 hour.

After nitration is complete the reaction flask is cooled to 80° C.

Planning An Aromatic Synthesis: Putting Reactions In The Right Order When planning a synthesis of simple aromatic compounds, it’s not enough to pick the right reactions. If you’re not careful, you may end up making a Up to now, we’ve covered electrophilic aromatic substitution [6 key reactions] [mechanism] [ortho-para-meta] and then the reactions of aromatic substituents [bromination & oxidation] [carbonyl reduction] [nitro reduction & Baeyer-Villiger]. So let’s start putting these reactions together in sequences with the goal of building specific molecules.

We’ll begin with a key principle for planning the synthesis of disubstituted aromatic molecules.

The addition of the acid will require about 1 hour.

After the acid has been added, the mixture is stirred for 2 hours longer at 90-100° C to complete the nitration. The upper layer consists largely of 2,4-dinitrotoluene, but probably contains a certain amount of 2,4,6-trinitrotoluene.One-half of it, corresponding to 50 g of toluene, is taken for the dinitration.The mononitrotoluene is dissolved in 109 g of concen­trated sulfuric acid (d=1.84 g/ml) while the mixture is cooled in running water.All the product is washed three or four times by agitating it vigorously with hot water under which it is melted.After the last washing, the TNT is granulated by allowing it to cool slowly under hot water while the stirring is con­tinued.If we just barrel along, doing bromination first and nitration second, what happens?Since the first reaction (bromination) installs an you have a list of some of the reactions needed to form/break these bonds, you need to ask a third question when planning a synthesis: “In what order do we run these reactions?In planning a synthesis, the order in which reactions are done can have a crucial impact on the outcome!Say you want to make this compound, This is where “order of operations” rears its potentially ugly head.The issue has to do with the Friedel Crafts alkylation and (to a slightly lesser extent) the Friedel-Crafts acylation reaction.It turns out that Friedel-Crafts reactions don’t work particularly well when strong electron-withdrawing groups (i.e – it’s that the reaction with electron-poor aromatic groups tends to be slower than side-reactions between the carbocations themselves.


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