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17 Reactions of Aromatic Compounds -- Part 21
Once considered a safe diet pill, methamphetamine is now addictive and destructive to brain tissue.
Parkinson's disease is thought to be caused by a dopamine deficiency.
The reduction of amides and the amination of carbonyl compounds are the two most general amine compounds.
Toluene, benzene, and alcohols with no more than four carbon atoms can be used as starting materials.
Para is the major product and separable from ortho.
Use any necessary reagents to show how you can accomplish the following steps.
The alkaloid coniine has been isolated.
Its formula is C8H17N.
Show how the reaction gives the observed product by proposing a complete structure for coniine.
A chemist is summoned to an abandoned waste-disposal site to determine the contents of a leaking barrel.
The smell of the barrel is overpowering.
The chemist takes a sample to her laboratory from the barrel and doesn't use a mask to approach it.
There are no absorptions above 3000 cm-1, no absorptions between 1500 and 2800 cm-1, and a strong absorption at 1200 cm-1 in the IR spec.
If you want to propose a structure for the unknown toxic waste, show what structural information is implied by each spectrum.
The EPA restricts the disposal of liquid waste because they leak out of their containers.
This waste can be converted to a solid form for reburial.
Suggest a way the chemist can remove the smell from her clothing.
Mild reagents and conditions are sufficient for Pyrrole to undergo aromatic substitution.
The following example shows that these reactions occur at the 2-position rather than the 3-position.
The acetylation of pyrrole is shown.
All the resonance structures of the intermediate should be drawn with care.
Section 17-12 shows how aromatic substitution can give aryl amines if there is a strong electron-drawing group.
Consider the following example.
There is a mechanism for this reaction.
The spectrum is followed by the IR.
One area 9 at d 0.9, one area 2 at d 1.0, and one area 2 at d 2.4 are shown in the NMR spectrum.
On shaking, the singlet at d 1.0 disappears.
A compound of formula C11H16N2 gives the IR, 1H NMR, and 13C NMR spectrum.
The peak at d 2.0 disappears when shaking with D2O.
Show how your structure accounts for the observed absorptions by proposing a structure for this compound.
A drug user responded to an ad in a magazine.
He flew from Colorado to Maryland and bought some P2P.
After waiting nearly a month for the suspect to make something, the police obtained a search warrant and searched the residence.
The suspect was not a good chemist and was unable to follow instructions from the person who gave him the P2P bottle.
They found bongs and pipes with marijuana and cocaine in them, as well as zinc strips, flasks, and other equipment.
You are a member of the jury.
Basicity is dependent on the availability of an electron pair.
In Section 19-10B, we saw that pyridine undergoes an aromatic substitution reluctantly, requiring strong conditions and disappointing yields.
The alkyl group is restricted to a 1deg or 2deg carbon byeductive amination of aldehydes and ketones.
Predict the products using the materials reported in the paper.
Show how the azo group can be used to facilitate aromatic substitution.
The macrolide antibiotics have large rings in which an ester makes the ring.
Some pathogenicbacteria have developed resistance to erythromycin by evolving an enzymatic mechanism to cleave the macrocycle at the ketone.
The erythromycin structure was modified to replace the ketone with an amine to counter the resistance.
One of the most prescribed drugs in the world for respiratory infections is a modified antibiotic called azithromycin.
The classification as macrolides requires you to identify the lactone group in each structure.
There are two groups.
You can identify the ketone in erythromycin as the site for detoxification.
Take a look at the amine in azithromycin.
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