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26. Amines

Amine Alkylation

26. Amines

Amine Alkylation

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General Reaction

General Reaction

Johnny Betancourt

Johnny Betancourt

Propose a Synthesis

Propose a Synthesis

Johnny Betancourt

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Textbook Question

Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA. b. Explain why it can cross-link DNA.

Textbook Question

In Section 10.12, we saw that S-adenosylmethionine (SAM) methylates the nitrogen atom of noradrenaline to form adrenaline, a more potent hormone. If SAM methylates an OH group attached to the benzene ring instead, it completely destroys noradrenaline's activity. b. Which reaction is more apt to occur, methylation on nitrogen or methylation on oxygen?

Textbook Question

Dimethylamine, (CH3)2NH, has a molecular weight of 45 and a boiling point of 7.4 °C. Trimethylamine, (CH3)3N, has a higher molecular weight (59) but a lower boiling point (3.5 °C). Explain this apparent discrepancy.

Textbook Question

Rank the following substituted anilines from most basic to least basic:

Textbook Question

Rank each set of compounds in order of increasing boiling points. (a) triethylamine, di-n-propylamine, n-propyl ether (b) ethanol, dimethylamine, dimethyl ether (c) diethylamine, diisopropylamine, trimethylamine

Textbook Question

In each pair of compounds, select the stronger base, and explain your choice. (a) HOCH2CH2NH2 or CH3CH2NH2 (b) PhNH2 or PhCH2NH2

Textbook Question

Within each structure, rank the indicated nitrogens by increasing basicity. (c)

Textbook Question

Within each structure, rank the indicated nitrogens by increasing basicity. (a)

Textbook Question

Rank each set of compounds in order of increasing basicity. (d) pyrrole, imidazole, 3-nitropyrrole

Textbook Question

Rank each set of compounds in order of increasing basicity. (c) aniline, pyrrole, pyridine, piperidine

Textbook Question

Rank each set of compounds in order of increasing basicity. (b) aniline, p-methylaniline, p-nitroaniline

Textbook Question

Predict the products of the following reactions: (a) excess NH3 + Ph-CH2CH2CH2Br →

Textbook Question

Propose a mechanism to show the individual alkylations that form this quaternary ammonium salt.

Textbook Question

What is the major product of the following reactions? c.

Textbook Question

Draw the product formed when pyridine reacts with ethyl bromide

Textbook Question

a. Explain why the reaction of an alkyl halide with ammonia gives a low yield of primary amine.

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Textbook Question

Show how you would convert alanine to the following derivatives. Show the structure of the product in each case.

(c) N-benzyloxycarbonyl alanine

(d) tert-butyloxycarbonyl alanine

Textbook Question

Within each structure, rank the indicated nitrogens

by increasing basicity.

(d) <IMAGE>

(e) <IMAGE>

Textbook Question

In each pair of compounds, select the stronger base, and explain your choice.

(c) <IMAGE>

(d) <IMAGE>

Textbook Question

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

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Textbook Question

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

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Textbook Question

Addition of one equivalent of ammonia to 1-bromoheptane

gives a mixture of heptan-1-amine, some dialkylamine, some

trialkylamine, and even some tetraalkylammonium bromide.

(a) Give a mechanism to show how this reaction takes place,

as far as the dialkylamine.

(b) How would you modify the procedure to get an

acceptable yield of heptan-1-amine?

Textbook Question

Rank the amines in each set in order of increasing basicity.

(a) <IMAGE>

Textbook Question

Rank the amines in each set in order of increasing basicity.

(e) <IMAGE>

Textbook Question

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) methylethylpropylisopropylammoniumiodide

Textbook Question

The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.

(c) Dopamine, one of the neurotransmitters in the brain. Parkinson’s disease is thought to result from a dopamine deficiency.

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Textbook Question

The ribonucleosides that make up ribonucleic acid (RNA) are composed of d-ribose (a sugar) and four heterocyclic “bases.” The general structure of a ribonucleoside is shown here.

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The four heterocyclic bases are cytosine, uracil, guanine, and adenine. Cytosine and uracil are called pyrimidine bases because their structures resemble pyrimidine. Guanine and adenine are called purine bases because their structures resemble purine.

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(b) Predict which nitrogen atoms are basic.

Textbook Question

Show how you would use direct alkylation to synthesize the following compounds.

(a) benzyltrimethylammonium iodide

(b) pentan-1-amine

(c) benzylamine

Textbook Question

Which of the following compounds are capable of being

resolved into enantiomers?

(d) 1,2,2-trimethylaziridine

(e) <IMAGE>

(f) <IMAGE>

Textbook Question

Predict the products of the following reactions.

(c) <IMAGE of reaction>

Textbook Question

(b) Show why p-nitroaniline is a much weaker base

(3 pKb units weaker) than aniline.

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Textbook Question

The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.

(a) Phenacetin, used with aspirin and caffeine in pain-relief medications.

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Textbook Question

The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.

(b) Methamphetamine, once considered a safe diet pill, but now known to be addictive and destructive to brain tissue.

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Textbook Question

Basicity depends on availability of an electron pair to bond a proton. Correlate structural effects in these amines with their basicities.

(a) Explain this order:

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Textbook Question

"Basicity depends on availability of an electron pair to bond a proton. Correlate structural effects in these amines with their basicities.

(b) Explain:

<IMAGE> is a stronger base than <IMAGE>"

Textbook Question

Basicity depends on availability of an electron pair to bond a proton. Correlate structural effects in these amines with their basicities.

(c) The pKb of this compound is −2.3, making it not only a stronger base than a typical aniline, but even stronger than hydroxide ion. Explain its remarkable basicity.

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Textbook Question

Rank the amines in each set in order of increasing basicity.

(d) <IMAGE>

Textbook Question

Within each structure, rank the indicated nitrogens by increasing basicity.

(f) <IMAGE>

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