Methodical Instruction for Students of the 2 Course Pharmaceutical Faculty
LESSON № 11 (PRACTICAL – 6 HOURS)
Themes: Phenols. Ethers. Small practicum.
Aim: To learn: the nomenclature, isomery, methods of extraction, physical and chemical properties of ethers and their thioanalogs, mono- and polyhydric phenols, naphthols, phenoloacids, quinines, aminophenols; their usage in the pharmacy.
Professional orientation of students.
Phenols are compounds that have a hydroxyl group bonded directly to a benzene or benzenoid ring. The parent compound of this group, C6H5OH, called simplyphenol, is an important industrial chemical. Many of the properties of phenols are analogous to those of alcohols, but this similarity is something of an oversimplification. Like arylamines, phenols are difunctional compounds; the hydroxyl group and the aromatic ring interact strongly, affecting each other’s reactivity. This interaction leads to some novel and useful properties of phenols.
The general formula of simple ethers is: R−O−R1
The radicals can be similar or different.
Methodology of Practical Class (900-1200).
Experiment 1. The extraction of diethyl ether.
Reagents: ethyl alcohol, H2SO4 (concentrated solution).
Technique of experiment. In a dry test-tube bring the mixture of ethyl alcohol and concentrated H2SO4 (1:1). Heat it very carefully to the boiling. After heating add 5-10 drops of ethyl alcohol. Diethyl ether can be determinate by smelling.
Write the equations of reactions.
Experiment 2. The extraction of complex ethers.
Reagents: ethyl alcohol, H2SO4 (concentrated solution), waterless sodium acetate, boric acid.
Technique of experiment.
a) The extraction of ethyl ether of boric acid. In a dry test-tube bring 1 g boric acid and heat it. When all crystals disappear, cool the test-tube. Add 2 ml of ethyl alcohol and 1 ml concentrated H2SO4. Close the test-tube by cork with gas-pipeline tube. Heat the mixture very carefully to the boiling. Ethyl ether of boric acid (triethylborate) (С2Н5О)3В evaporates, because it boils at the temperature of 117,3°С. Burn the gas near the opening of gas-pipeline tube. The gas burns with greenish flame. You can use also a copper wire.
2Н3ВО3 
В2О3 + 3Н2О
В2О3 + 6С2Н5ОН ® 2(С2Н5О)3В + 3Н2О
b) The extraction of ethyl acetate. In a dry test-tube bring 2 ml of waterless sodium acetate and add 3 drops of ethyl alcohol. Add 2 drops of concentrated H2SO4 and heat the mixture very carefully. The smell of ethyl acetate appears.
Write the equations of reactions.
Experiment 3. Formation of oxonium compounds.
Reagents: diethyl ether, concentrated sulfate acid.
Technique of experiment. In a dry test–tube bring 5 drops of concentrated sulfate acid. Content Cool the mixture in the ice. Carefully, at the cooling and shaking, add 5drops of diethyl ether. The smell of diethyl ether disappears:
At the shaking and cooling add in the tube 5 drops of cool water. Observe Formation of two layers of solution and feel characteristic smell of diethyl ether:
In the reaction of simple ethers with concentrated mineral acids (exothermic) oxonium salts formed, which easily hydrolyze by water and have general formula:
where Х– – halogen ion or residue of acid.
Experiment 4. Detection of the peroxide compounds in diethyl ether.
Reagents: diethyl ether, 2% potassium iodide solution, 0,5% starch solution, 5% iron (ІІ) sulfate solution, iodostarch paper.
At the long or not correct storage diethyl ether oxidizes under the action of air oxygen and light with the formation of peroxide compounds, which can case explosion.
Attention! Can not be conducted distillation of diethyl ether or determination of its boiling temperature without previous sample on peroxide compounds! Don’twork with ethers that have solid precipitate!
Technique of experiment. Put to the test–tube 5 drops of diethyl ether and 1 drop of 2% potassium iodide solution. Content of the tube is energy shacked. When thereare peroxide compounds that form at the interaction with air oxygen, observe appearance of the yellow color of enteric layer (elimination of iodine):
If the coloration is not observable, add to the test-tube 2 drops of 0,5% solution of starch. Observe the formation of intense blue, cased by formation of complex between starch and iodine.
Presence of peroxide compounds in ethers also can be identified with iodostarch paper, soaked in chloride acid. In the presence of peroxide compounds observeintense blue color.
When the sample with potassium iodide solution ether is mixed with iron (II) sulfate for the decomposition of peroxide compounds. Oxidation of Fe2+ in Fe3+ takes place and destroying of peroxide compounds.
Experiment 5. The acidic properties of phenol.
Reagents: phenol (5% solution), NaOH (0,02% solution), phenolphthalein (1% solution).
Technique of experiment. In a test-tube bring 2 ml of NaOH (0,02% solution) and add several drops of phenolphthalein. The pink color appears. Add phenol (5% water solution). The color disappears. It means that phenol has acidic properties. That’s why it can be named as carboxylic acid.
Experiment 6. The extraction of sodium phenolate and determination of its properties.
Reagents: phenol (solid), NaOH (2N solution), HCl (20% solution).
Technique of experiment. Bring to the test-tube 2-3 crystals of phenol (Be careful! Phenol gives strong burns!) Then in each test-tube add 2N sodium hydroxide solution. Phenol dissolves completely in sodium hydroxide, after this to the transparent solution of sodium phenolate add 1-2 ml of 20% chloride acid solutionрозчину. Observe that at first phenol eliminates in the form of white turbidity, then – in the form of oil drops, which form sediment on the tube bottom. So, acidicproperties of phenol are weakest then acidic properties of chloride acid.
Experiment 7. Comparison of phenol and 2,4,6–trinitrophenol acidic properties.
Reagents: phenol (crystals), NaHCO3 (10% solution), picric acid (crystals); sodium hydrocarbonate (10% solution); lime water.
Technique of experiment. Take two test-tubes. Bring to the first test-tube several crystals of phenol and to the second test-tube bring several crystals of picric acid. After this in each tube add 2 ml of 10% sodium hydrocarbonate solution. Observe that picric acid actively interacts with sodium hydrocarbonate solution. As a result of this reaction CO2 evaporates. Close the tube with reaction mixture, which contains picric acid and sodium hydrocarbonate, by cork with gas–pipeline tube, endof this tube immerse in another tube with 2 ml of lime water.
What do you see?
Phenol does not react with sodium hydrocarbonate solution.
So, acidic properties of 2,4,6-trinitrophenol are strongest then acidic properties of phenol, that’s why phenol does not force out carboxylic acid from sodiumhydrocarbonate and 2,4,6-trinitrophenol forces out this acid from its salts.
Explain why acidic properties of picric acid are strongest then acidic properties o9f phenol.
Compare acidic properties of phenol with acidic properties of p–methylphenol, p–chlorophenol, benzyl alcohol and p–nitrobenzyl alcohol.
Experiment 8. The reaction of phenols with FeCl3.
Reagents: phenol (5% water solution), p-cresol (5% water solution), m-cresol (5% water solution), resorcinol (5% water solution), hydroquinone (5% water solution), pyrogallol (5% water solution), pyrocatechol (5% water solution), ethyl alcohol, FeCl3 (5% solution).
Technique of experiment. The experiment is run with 5% solutions of phenol, p-cresol, m-cresol, resorcinol, hydroquinone, pyrogallol and pyrocatechol. Bringto the test–tube 1 ml of appropriate phenol solution and add 1 drop of 5% solution of iron (III) chloride. Observe painting of the reaction mixture in intense color: (phenol – purple, p-cresol – dark-blue, m-cresol – red-violet, resorcinol – purple, hydroquinone – green and then brown (at the standing beautiful dark green crystals ofquinhydrone fall), pyrogallol – red, pyrocatechol – olive-green and can changes to violet-blue after the strong dilution with water).
Appearance of the coloration after the adding of iron (III) chloride to the appropriate phenol cased by the formation of complex phenolates:
This reaction is qualitative reaction on phenol (enol) hydroxyl.
The presence of water in reactionary mixture is very important, because water causes the forming of complex compounds. If you add the same volume of alcohol to the complex compound in the test-tube, the color disappears.
Experiment 9. Brominating of phenol.
Reagents: phenol (5% water solution), bromine water (saturated water solution).
(Experiment is conducted under the ventilation cupboard!)
Technique of experiment. In a test-tube bring 2-3 ml of bromine water and add phenol (5% water solution) by drops. Observe discoloration of bromine water andturbidity of reaction mixture, then the white precipitate forms (2,4,6-tribromophenol). Add 1-2 ml of bromine water again and mix the mixture. The color of bromine water disappears and precipitate color chances from white to light yellow. If you add bromine in excess 2,4,6–tribromophenol transforms in 2,4,4,6-tetrabromocyclohexadienone.
Explain why phenol discolors bromine water and benzene does not react with bromine water.
Experiment 10. Nitrating of phenol.
Reagents: phenol (crystal), nitrate acid (water solution, density ρ = 1,11 g/cm3).
Technique of experiment. In a test-tube bring 1 g of phenol and add 4-5 drops of water. (Be careful! Phenol gives strong burns!) Add 2-3 ml of nitrate acid (ρ = 1,11 g/cm3) by drops. Mix the reaction mixture and put to standing. After 15 minutes add 5-6 ml of water. Then, after standing, separated water solution of nitrate acid from dark oil layer of o- and p-nitrophenols mixture. To the obtained mixture of o- and p-nitrophenols add 1 ml of water. Close the test-tube by the cork with gas-pipeline tube and deep the end of this tube into the receiver test-tube (fig. 1). Heat the mixture to boiling and distill the mixture of water with o-nitrophenol into the receiver test-tube. Then o-nitrophenol crystallizes (yellow crystals with the smell of bitter almond).
Figure 1. Scheme of devise for the phenol nitrating
p-Nitrophenol does not evaporates and leaves in the resin mass of reaction mixture.
Explain why o-nitrophenol distills with water steam and p-nitrophenol does not have this ability.
Experiment 11. Oxidation of phenol.
Reagents: phenol (5% water solution), KMnO4 (1% solution).
Technique of experiment. In a test-tube put 1 ml of phenol (5% water solution) and add 2 ml of KMnO4 (1% solution). Mix the mixture. The color of solution changes and brown precipitate forms (MnO2). So, phenol can be easily oxidizes. During the processes of phenol oxidation at first hydroquinone forms and then, afterfollowing oxidation, p–quinone forms.
Write the equation of reaction of phenol and potassium permanganate in neutral medium.
Experiment 12. Reductive properties of polyhydric phenols.
Reagents: pyrocatechol (5% water solution), resorcinol (5% water solution), hydroquinone (5% water solution), pyrogallol (5% water solution), Fehling solution I and II, AgNO3 (1% solution), NH4OH (5% solution).
Technique of experiment. To the 4 test-tubes put 0,5 ml of Fehling solution I and 0,5 ml of Fehling solution II. Then to the first test-tube add 2 mlofhydroquinone (5% water solution), to the second one – 2 ml of resorcinol (5% water solution), to the third test-tube add 2 ml of pyrocatechol (5% water solution) and to the forth test-tube add 2 ml of pyrogallol (5% water solution). Heat the mixtures on the boiling water heater. The red precipitate of Cu2O forms.
Do the same experiments with AgNO3 (1% solution) and NH4OH (5% solution). As the result of this reaction black precipitate of Ag forms.
So, polyhydric phenols can easy oxidize. That is why they have reductive properties. They reduce Fehling solution and silver from its oxide.
Experiment 13. Oxidation of pyrogallol by O2 from the air.
Reagents: pyrogallol (solid), NaOH (10% solution).
Technique of experiment. In a test-tubes put 0,2-0,3 g of pyrogallol and 2-3 ml 10% NaOH. Construct the device as is shown on the figure 2. Close the test-tube by the cork with gas-pipeline tube and immerse the end of gas-pipeline tube into the second test-tube with 5-6 ml of water. Shake the test-tube with reaction mixture. The mixture becomes black, because pyrogallol oxidizes by O2. As a result of absorption of oxygen in the test–tube with reaction mixture rarity appears. That is why water from the second test-tube sucks in and rises by the curved tube.
Fig. 2. The device for oxidation of pyrogallol by O2 from the air.
So, pyrogallol can easy oxidize by O2 from the air. That is why it is used for absorption of oxygen in gas-analyzers.
Experiment 14. The extraction of quinhydrone.
Reagents: quinone (p–benzoquinone) (saturated aqueous solution); hydroquinone (saturated aqueous solution).
Technique of experiment. In a test-tubes bring 1 ml of saturated aqueous quinine solution and 1 ml of saturated aqueous hydroquinone solution. Mix the mixture. The dark-green crystals of quinhydrone form.
In quinhydrone molecules of quinine and hydroquinone connected by hydrogen bounds. Except this, in qiunhydrone molecule the charge is brought fromhydroquinone to quinine. Hydroquinone is a donor of electrons and quinine is an acceptor.
Quinhydrone is used as electrode for the determination of Н+-ions concentration in a solution.
Experiment 15. α– and β-naphthols and its properties.
Reagents: α-naphthol, β-naphthol, NaOH (10% solution), bromine water (saturated solution), ethyl alcohol, FeCl3 (5% solution).
Technique of experiment.
a) The forming of naphtholates. In a test-tubes bring 0,1 g of α-naphthol (or β-naphthol) and 1-2 ml of water. Naphthol does not solve in water. Add 10% NaOH.Naphthol dissolves in NaOH. So, naphthols have acidic properties and react with alkalis.
b) The intereaction of α-naphthol and β-naphthol with FeCl3. In 2 test-tubes bring 1-2 ml of ethyl alcohol. In the first test-tube add several crystals of α-naphtholand in the second one – several crystals of β-naphthol. Heat the mixtures to the complete dissolution of naphthols. In 2 test-tubes with alcohol solutions add several drops of FeCl3 (5% solution). In the first test-tube violet complex compound forms, in the second one – dark-green complex compound forms. So, naphthols (like phenols) with FeCl3 can form color complex compounds.
c) Reaction between naphthols and bromine water. In the first test-tube bring several crystals of α-naphthol and in the second one – several crystals of β-naphthol. In 2 test-tubes add 1 ml of bromine water. Mix the mixtures in 2 test-tubes. Observe discoloration of the mixture. So, naphthols react with bromine water like phenols.
Basic concepts of theme
Composition – Structure – Properties
Hydroxi-group
Zajtsev rule
Simple ether
Complex ether
Carbinol
Contraction
Acydolysis
Sulfoxide
Phenol
Aminophenol
Naphthol
Quinone
Individual Students Program.
1. Classification, nomenclature and isomery of ethers and their thioanalogs.
2. Methods of obtaining of ethers and their thioanalogs.
3. Physical and chemical properties of ethers and their thioanalogs:
1) formation of oxonium salts;
2) decomposition of ethers under the action of mineral acids (acidolysis) and metallic sodium;
3) oxidation.
4. Physical and chemical properties of thioethers:
1) formation of sulfonium salts;
2) interaction with the salts of hard metals;
3) oxidation (sulfoxides, sulfones).
5. Identification of ethers and thioethers.
6. Classification, isomery and nomenclature of phenols.
7. Methods of receiving of phenols.
8. Physical properties of monoatomic phenols:
1) reactions with the participants of О—Н-bound (acidic properties, formation of ethers and esters and eaters);
2) reactions of electrophillic substitutions (SE) in aromatic ring (halogenation, nitration, sulfonation, nitrosation, alkylation, acylation, azoconnection,carboxylation (synthesis of phenolocarboxylic acids), carbonylation (synthesis of hydroxialdehydes), hydroximethylation;
3) reduction;
4) oxidation.
9. Di– and triatomic phenols. Chemical properties.
10. Aminophenols. Methods of obtaining. Chemical properties.
11. Identification of alcohols.
12. Some representatives.
13. Naphthols.
14. Phenoloacids. Quinones.
15. Aminophenols. Preparations, derivatives of aminophenols.
Seminar discussion of theoretical issues (1230 – 1400 hour).
Test evaluation and situational tasks.
Home task: 1,3, 7, 10.
1. Name the following compounds by radical–functional and systematic nomenclature::
2. Which of the following ethers can be obtained by intermolecular dehydration of alcohols?
3. Explain the answer.
4. Write the scheme of diisopropyl ether obtaining from halogenalkane. What halogenalkane is previously used I this reaction? Specify the substrate and nucleophillicreagent in this reaction.
5. Write two methods of the dimethyl ether obtaining and name it by the IUPAC nomenclature. Explain the difference in boiling temperatures of dimethyl ether and ethanol. Write and name the products of interaction of: а) diethyl ether and hydrogen chloride (oxonium compound); b) dibutyl ether and oxidant (peroxide).
6. What products will form after the nucleophillic decomposition of methylpropyl ether by iodide acid? Write the scheme of reaction. Specify the mechanism of reaction.
7. What products will form after the nucleophillic decomposition of methyltret-butyl ether by iodide acid? Write the scheme of reaction. Specify the mechanism of reaction.
8. Write the structural formulas of the following compounds: 1) о-nitrophenol; 2) p–cresol; 3) pyrocatechol; 4) resorcinol; 5) hydroquinone; 6) pyrogallol; 7)oxihydroquinone; 8) phloroglucinol; 9) picric acid; 10) thiophenol; 11) m–nitrothiophenol; 12) 4-chloro–mercaptobenzene.
9. Name the following compounds by the systematic nomenclature and point their atomicity:
10. Write the schemes of phenol synthesis by the usage of the following compounds as a primer: 1) benzenesulfoacid; 2) chlorobenzene; 3) cumene(isopropylbenzene); 4) benzenediazonium chloride. Specify the reaction conditions.
11. Write the reaction schemes that allowed to synthesize the following compounds: 1) resorcinol from benzene; 2) p–cresol from p–toluicine; 3) m–nitroanizol from nitrobenzene; 4) pyrogallol from gallic acid; 5) 2,4,6-tribromophenol from chlorobenzene.
12. Put the following compounds in the row of acidic properties decreasing: 1) phenol, water, carbonate acid, ethanol; 2) thiophenol, ethanol, phenol; 3) resorcinol,methanol, pyrogallol, phenol; 4) p–nitrophenol, benzyl alcohol, m–nitrophenol, 2,4,6-trinitrophenol, 2,4-dinitrophenol; 5) p–cresol, p–chlorophenol, p–methoxyphenol, phenol, p–nitrophenol. Explain the answer.
13. Write the reactions of phenol, n-nitrophenol and 2,4,6-trinitrophenol with following reagents: 1) NaОН (Н2О); 2) NaНСОз (Н2О). Write equations of reactions and name the products.
14. Write the schemes of reactions of phenol with such reagents: 1) КОН (Н2О); 2) conc. НNO3; 3) dil. НNО3; 4) conc. Н2SО4 (100 °С); 5) (СН3СО)2О; 6)NаОН, then СН3І; 7) conc. Н2SО4 (-20 °С); 8) NаNО2 (НС1); 9) СН3СОС1 (А1С13); 10) Н2 (Nі); 11) СrO3, Н+; 12) СН3МgВг; 13) С2Н5ONа (С2Н5ОН); 14) ЗВг2 (Н2О); 15) NаОН, then С6Н5NNСl; 16) 2Вг2 (ССl4); 17) NаОН, then СН3СОС1; 18) СНС13, NаОН (Н2О). Name the products.
15. Compare the ratio of phenol and benzyl alcohol with the action of these reagents: 1) Nа; 2) NаОН (Н2О); 3) СН3СООН (conc.Н2S04); 4) РС15; 5) СН3СОС1; 6) conc. НNO3; 7) Вr2 (Н2О); 8) conc. Н2SО4 (100 °С). Write the reactions and name the products.
16. Using as a starting compound of phenol present synthesis scheme:
1) p–bromophenylacetate; 2) p–nitrophenetol; 3) p–hydroximethylphenol; 4) p–nitrosophenylbenzoate.
17. Compare the action of phosphorus (V) chloride, HCl and thionylchloride on phenol and ethanol. Explain why phenol unlike alcohol does not react withreplacement (SN) of phenolic hydroxyl.
18. Compare basic and nucleophilic properties of phenol and sodium phenolate.
19. Explain why at the heating of phenol with acetic acid phenylacetate practically does not form. What reagents can be used to conduct О-alkylation and О-acylationof phenol? Write the appropriate equations of reactions.
20. Describe reactivity of the phenoxide-ion in the SE reactions. Write schemes and mechanisms of the interaction of sodium phenoxide with following reagents: 1) СО2, t, р; 2) СНС13, NаОН (Н2О); 3) formaldehyde (Н+). Name the products. What is the practical significance of these reactions?
21. Place the listed compounds in order of reactivity increasing in the SE reactions: 1) p–nitrophenol, p–aminophenol, p–cresol, p–chlorophenol, m–nitrophenol, 2,4,6-trinitrophenol; 2) thiophenol, phenol, p-aminothiophenol, p–nitrophenol; 3) sodium phenolate, benzyl alcohol, phenol. Explain the answer.
22. Write to the scheme of possible chemical reactions that allow you to distinguish these compounds: phenol and benzyl alcohol.
23. Why alkylation of phenol should be conducted in an alkaline environment? Specify the reaction scheme of phenol ethylation. What is the mechanism of thisreaction?
24. Name the color reaction on the detection of phenols and indicate which of them will give the coloration with iron (ІІІ) chloride: benzyl alcohol, hydroquinone,phenetol, phenol, resorcinol, ethylene glycol. Write the schemes of reactions.
25. Complete the transformation scheme, name the products, reactions, provide mechanisms for individual reactions:
26. Propose the scheme of p–nitrophenol obtaining fro the appropriate reagents.
27. Complete the transformation scheme, name the products, reactions, provide mechanisms for individual reactions:
28. What is the end-product of the following reaction?
A.
B.
C.
D.
E.
29. Choose the mechanism of the following reaction?
A. SE
B. SN1
C. SN2
D. SR
E. AN
30. From the following compounds choose the structure of phloroglucinol.
A.
B.
C.
D.
E.
31. Which reagents and conditions are used to obtain phenol from benzoic acid?
A. Н2, cat., t˚
B. О2, t˚
C. KMnO4, t˚
D. H2SO4; t˚
E. О2, Н2О, Cu2+ , t˚
Correct answers of test evaluations and situational tasks:
28. B; 29, D; 30. D; 31. E.
Individual student work (1415-1500 hour) are checked by solving situational tasks for each topic, answers in test evaluations and constructive questions (the instructor has tests & situational tasks).
Student should know:
– the structure, nomenclature, isomery, methods of extraction and chemical properties of ethers, phenols and naphtols.
– the determination of physical constants of organic compounds (melting temperature, boiling temperature).
Student should be able to:
-to carry out reactions that characterize the chemical properties of ethers, phenols and naphthols;
References:
Main:
1. Clayden Jonathan. Organic Chemistry. Jonathan Clayden, Nick Geeves, Stuart Warren // Paperback, 2nd Edition. – 2012. – 1234 p.
2. Bruice Paula Y. Organic Chemistry / Paula Y. Bruice // Hardcover, 6th Edition. – 2010. – 1440 p.
3. Brückner Reinhard. Organic Mechanisms – Reactions, Stereochemistry and Synthesis / Reinhard Brückner // Hardcover, First Edition. – 2010. – 856 p.
4. Moloney Mark G. Structure and Reactivity in Organic Chemistry / Mark G. Moloney // Softcover, First Edition. – 2008. – 306 p.
5. Carrea Giacomo. Organic Synthesis with Enzymes in Non-Aqueous Media / Giacomo Carrea, Sergio Riva // Hardcover, First Edition. – 2008. – 328 p.
6. Smith Michael B. March’s Advanced Organic Chemistry. Reactions, mechanisms, and structure / Michael B. Smith, Jerry March // Hardcover, 6th Edition. – 2007. – 2384 p.
7. Carey Francis A. Advanced Organic Chemistry / Francis A. Carey, Richard A. Sundberg // Paperback, 5th Edition. – 2007. – 1199 p.
9. http://intranet.tdmu.edu.ua/data/kafedra/internal/zag_him/presentations/pharmaceutical/pharmacy/full_time_study/organic_chemistry/2_course/lecture_06. Alcohols. Phenols. Ethers.
Additional:
1. Francotte Eric. Chirality in Drug Research / Eric Francotte, Wolfgang Lindner //
Hardcover, First Edition. – 2006. – 351 p.
2. Quin Louis D. Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals / Louis D. Quin, John Tyrell // Hardcover, 1st Edition. – 2010. – 327 p.
3. Zweifel George S. Modern Organic Synthesis – An Introduction / George S. Zweifel, Michael H. Nantz // Softcover, 1st Edition. – 2007. – 504 p.
4. K. C. Nicolaou. Molecules that changed the World / Nicolaou K. C., Tamsyn Montagnon // Hardcover, First Edition. – 2008. – 385 p.
5. Mundy Bradford P. Name Reactions and Reagents in Organic Synthesis / Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro // Hardcover, 2nd Edition. – 2005. – 886 p.
6. Li Jie Jack. Name Reactions. A Collection of Detailed Reaction Mechanisms / Jie Jack Li // Hardcover, 4th Edition. – 2009. – 621 p.
7. Gallego M. Gomez. Organic Reaction Mechanisms / M. Gomez Gallego, M. A. Sierra // Hardcover, First Edition. – 2004. – 290 p.
8. Sankararaman Sethuraman. Pericyclic Reactions – A Textbook / Sethuraman Sankararaman // Softcover, First Edition. – 2005. – 418 p.
9. Tietze Lutz F. Reactions and Syntheses / Lutz F. Tietze, Theophil Eicher, Ulf Diederichsen // Paperback, First Edition. – 2007. – 598 p.
10. Olah George A. Superelectrophiles and Their Chemistry / George A. Olah, Douglas A. Klumpp // Hardcover, First Edition. – 2007. – 301 p.
11. Grossmann Robert B. The Art of Writing Reasonable Organic Reaction Mechanisms / Robert B. Grossmann // Hardcover, 2nd Edition. – 2003. – 355 p.
12. Cole Theodor C.H. Wörterbuch Labor – Laboratory Dictionary / Theodor C.H. Cole // Hardcover, 2nd Edition. – 2009. – 453 p.
The methodical instruction has been worked out by: associate prof. Dmukhulska Ye.B., assistant Medvid I.I., assistant Burmas N.I.
Methodical instruction was discussed and adopted at the Department sitting
25.06.2013. Minutes N 11
Methodical instruction was adopted and reviewed at the Department sitting
27.08.2013. Minutes N 1
