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Chapter 19: Q24P (page 1014)
Propose a mechanism for the synthesis of methyl orange.
Step 1:
Step 2:
Step 3:
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Which of the amines listed next is resolved into enantiomers? In each case, explain why interconversion of the enantiomers does or does not take place.
(a)Cis-2-methylcyclohexanamine
(b) N-ethyl-N-methylcyclohexanamine
(c) N-methylaziridine
(d) Ethylmethylanilinium iodide
(e) Methylethylpropylisopropylammonium iodide
Reductive amination of aldehydes and ketones is a versatile method for attaching alkyl groups to amines, but the alkyl group is restricted to a 1 0or 20carbon by this method. Prof. Phil Baran of Scripps Research Institute has reported (Science, 2015, 348(6237), 886-891) a novel way to reduce an aromatic nitro group and add the resulting amine to an alkene so that the aromatic amine is bonded to a carbon- all in a continuous sequence of reactions. For example:
Predict the products using these starting materials, all of which are reported in this paper.
What would happen in the synthesis of sulfanilamide if the amino group were not protected as an amide in the chlorosulfonation step?
Propose a mechanism for nitration of pyridine at the 4-position, and show why this orientation is not observed.
Macrolide antibiotics all have large rings (macrocycle) in which an ester makes the ring; a cyclic ester is termed a lactone. One example is erythromycin A, first isolated from soil bacteria in the 1950’s. Over time, some pathogenic bacteria have developed resistance to erythromycin by evolving an enzymatic mechanism to cleave the macrocycle at the ketone. To counter this resistance, chemists modified the erythromycin structure to replace the ketone with an amine that the bacteria could not detoxify. This modified antibiotic, azithromycin, trade name Zithromax®, is one of the most prescribed drugs in the world for respiratory infections.
(a) Identify the lactone group in each structure that merits the classification as macrolides.
(b) Two groups are circled. What type of functional group are they? Explain
(c) Identify the ketone in erythromycin targeted by bacteria as the site for detoxification.
(d) Identify the amine in azithromycin. What type of amine is it?
(e) From what you know about the reactivity of ketones and amines, why was an amine a good choice to be the “chemical opposite of a ketone”?
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