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Chapter 19: Q59P (page 1035)

(A true story.) A drug user responded to an ad placed by a DEA informant in a drug-culture magazine. He later flew from Colorado to Maryland, where he bought some 1-phenyl-2-propanone (P2P) from the informant. The police waited nearly a month for the suspect to synthesize something, then obtained a search warrant, and searched the residence. They found the unopened bottle of P2P; apparently, the suspect was not a good chemist and was unable to follow the instructions the informant gave him. They also found pipes and bongs with residues of marijuana and cocaine, plus a bottle of methylamine hydrochloride, some muriatic acid (dilute HCL), zinc strips, flasks, and other equipment.

(a) Assume you are consulting for the police. Show what synthesis the suspect was prepared to carry out, to provide probable cause for the charge of attempting to manufacture a controlled substance.

(b) Assume you are a member of the jury. Would you convict the defendant of attempting to manufacture a controlled substance?

Short Answer

Expert verified

(a)

(b) Yes, the defendant should be convicted on the charge of attempted manufacture of methamphetamine.

Step by step solution

01

Explanation of part (a):

The acid-catalyzed condensation of P2P (a controlled substance) with methylamine hydrochloride gives an imine which can be reduced to methamphetamine.

The suspect was probably planning to use zinc in muriatic acid for the reduction.

Synthesis of methamphetamine

02

Explanation of part (b):

Yes, the defendant should be convicted on the charge of attempted manufacture of methamphetamine. There were legal problems with possible entrapment, plus the fact that he had never opened the bottle of the starting material. The defendant should be convicted on several possession charges.

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Most popular questions from this chapter

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”?

Show how the substituents containing the azo group () can facilitate both electrophilic and nucleophilic aromatic substitution.

A.Hafner and S.Brase, Angewandte Chemie Int. Ed., M.Heinrich et al., Journal of Organic Chemistry, 2012, 77, 1520. 2012, 51, 3713

a) Guanidine (shown) is about as strong base as hydroxide ion. Explain why guanidine is a much stronger base than most other amines.

(b) Show why p-nitroaniline is a much weaker base (3 pKb units weaker) than aniline.

(c) Explain why N,N-2,6-tetramethylaniline (shown) is a much stronger base than N,N-dimethylaniline.

Rank each set of compounds in order of increasing basicity

(a) NaOH, NH3, CH3NH2, Ph-NH2

(b) aniline, p-methylaniline, p-nitroaniline

(c) aniline, pyrrole, pyridine, piperidine

(d) pyrrole, imidazole, 3-nitropyrrole

Question. (a) Show how fragmentation occurs to give the base peak at m/z 58 in the mass spectrum of ethyl propyl amine (N-ethylpropan-1-amine), shown below.

(b) Show how a similar cleavage in the ethyl group gives an ion of m/z72.

(c) Explain why the peak at m/z 72 is much weaker than the one at m/z 58.
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