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17 Reactions of Aromatic Compounds -- Part 18
When tertiary amines are treated with a peroxyacid and heated, give the products expected.
The major product has a structure.
The Zaitsev product is also formed.
Stereochemical drawings of the transition states can be used to explain the observations.
N O are useful for synthesis.
In an acidic solution, nitrous acid may lose water and give the nitro sonium ion.
Most reactions of amines with nitrous acid use the nitrosonium ion as the intermediate.
The most useful products come from the reactions of amines with nitrous acid.
The diazonium ion is caused by the loss of water and the hydroxy group.
Alkanediazonium salts are not stable.
They give nitrogen gas and carbon dioxide.
The formation of N2 is the driving force for this reaction.
The reactions generated in this manner are similar to others we have seen.
Complex mixture of products are usually given by the decomposition of alkanediazonium salts.
The diazotization of primary alkylamines is not used for synthesis.
Arenediazonium salts are relatively stable and serve as intermediates in a variety of synthetic reactions.
Section 19-17 talks about these reactions.
The tautomerism is formed by a diazonium ion with a primary amine.
The reaction mixture is usually an oily liquid.
Experiments show thatnitrosoamines cause cancer in laboratory animals.
The use of sodium nitrite to preserve meats such as bacon, ham, and hot dogs has generated concern.
Because nitrites are naturally present in many other foods, it's not clear how much risk is involved in preserving meats.
There is more research being done in this area.
The most useful reaction of amines is the reaction of arylamines to form arenediazonium salts.
Next, we look at how these salts may be used as synthetic intermediates.
In comparison to alkanediazonium salts, arenediazonium salts are relatively stable.
A primary aromatic amine is diazotizing the Arenediazonium salts.
An activated aromatic position can be converted into a wide variety of functional groups by forming and diazotizing an amine.
When the acidic solution of an arenediazonium salt is warmed, hydrolysis takes place.
A phenol is formed by the hydroxy group of water.
This is a useful laboratory synthesis of phenols because it does not require strong electron-drawing substituents or powerful bases.
The diazo nium salts have a special affinity for copper salts.
Aryl Chlorides, aryl bromides, and aryl cyanides are produced when cuprous chloride, cuprous bromide, and cuprous cyanide react with arenediazonium salts.
The Sandmeyer reaction is an excellent method for attaching carbon substituent to an aromatic ring.
The aryl fluoride can be given if this precipitated salt is heated.
There are few ways to make aryl fluorides.
Parkinson's disease causes the death of dopamine- producing neurons by causing Aryl iodides to form.
One of the best ways to make iodobenzene derivatives is by causing a severe in the brain.
Hypophos phorus acid replaces the diazonium group with a hydrogen.
This is a reduction of the arenediazonium ion.
Sometimes this reaction is used to remove an added group from the ring.
How one might use this technique is shown in a solved problem.
3,5-dibromotoluene can only be given by direct bromination of toluene.
bromination to its ortho positions is directed by the strongly activated amino group.
The desired product can be given if the amino group is removed.
diazonium salts only react with strongly activated rings because they are weak electrophiles.
There is a mechanism for the synthesis of orange.
Azo compounds bring two aromatic rings into conjugate with an azo group.
Many azo dyes are made with diazo.
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