SYLLABUS GM 2019-20 English

«С.Ж.
АСФЕНДИЯРОВ АТЫНДАҒЫ ҚАЗАҚ ҰЛТТЫҚ МЕДИЦИНА УНИВЕРСИТЕТІ» КЕАҚ

НАО «КАЗАХСКИЙ НАЦИОНАЛЬНЫЙ МЕДИЦИНСКИЙ УНИВЕРСИТЕТ ИМЕНИ С.Д. АСФЕНДИЯРОВА»
Redaction: 1
Chemistry Department Syllabus Page 1 from 63
«С.Ж. АСФЕНДИЯРОВ АТЫНДАҒЫ ҚАЗАҚ ҰЛТТЫҚ МЕДИЦИНА УНИВЕРСИТЕТІ» КЕАҚ
Redaction: 1
Information to contact:
Redaction: 1
Information about teachers

№ Full name Position Academic e-mail
degree
1. Myrzakozha Diyas Asylbekovich Head of D.Sc. myrzakozha.d@kaznmu.
department kz
2. Karlova Elmira Karlovna associate
Ph.D. karlova.e@kaznmu.kz
professor
3. associate almabekova.a@kaznm
Almabekova Alma Amirbekovna Ph.D.
professor u.kz
4. associate nechepurenko.e@kazn
Nechepurenko Elena Viktorovna Ph.D.
professor mu.kz
Policy of the discipline:

Student responsibilities:
▪ to behave according the Rules of academic honesty at all stages of the educational process; it is
forbidden to use mobile devices / gadgets, headphones, and other means of information service, cheat
sheets during any kind of control, including current and midterm controls, exam; otherwise the answer
is canceled with the subsequent drawing up of the act / removal from the exam and the mark "0" is
set;
▪ attend practical/laboratory classes and take the break time according to the schedule;.
▪ always be ready for practical / laboratory classes, for current and midterm examinations, exam;
▪ extracurricular classes are consultations; they are attended in the following cases: (1) student has
questions to the teacher; (2) student needs to pass self-study work tasks or topics of missed classes
(only with the permission of the dean's office).
▪ complete the tasks within the terms determined by the syllabus in discipline;
▪ do not miss classes for no reason; in case of absence for serious reason, provide permission from the
dean office to pass topics of missed classes;
▪ comply with safety regulations;
▪ do not spoil the books of the library fund of the University and property of the department: furniture,
equipment, instruments, tools, reagents etc.;
▪ comply with the subordination and basic ethical principles in relation to all participants in the
educational process (faculty, teaching support staff of the department and students);
▪ honestly discuss conflict situations (if they happen) in the group, with the participation of the group
teacher, head teacher and department head;
▪ leave the classroom / classroom during class time without the permission of the teacher;
▪ attend the exam according to the schedule, with a student`s book.
Student rights:
▪ get electronic version of syllabus on discipline;
▪ receive timely information about the grades received;
▪ receive reasoned justification for the grade;
▪ answer missed topic to the teacher (only with the permission of the dean's office), as well as
appropriate self-study questions;
▪ to get advice on the discipline course issues that caused difficulties as well as questions for self-
study (according to the schedule);
▪ receive additional tasks in order to increase the current assessment (except for midterm control) no
more than twice per semester;
Redaction: 1
▪ appellate for examination assessment in the prescribed manner.
Dress Code Requirements

▪ wearing a clean ironed medical gown;
▪ accurate clothing;
▪ have a neat hairstyle (for girls: no loose hair).
Penalties
▪ In case of a single violation of the discipline policy, the student receives an oral warning from the
teacher.
▪ In case of repeated violations of discipline policy, the student provides an explanatory note
addressed to the head of the department.
▪ With a systematic violation of discipline policy, the head of the department submits the appropriate
report to the dean’s office.
▪ For an undone task / absence in the lesson, the student receives “0” points, which will affect his
total assessment.
▪ If the Rules of academic honesty are not observed at all stages of the educational process, the answer
is canceled and a rating of “0”.
Purpose of the course unit

the formation of basic concepts about the physico-chemical nature of the processes and phenomena
occurring in the body and the skills of their application in the study of special subjects and research
Brief description of the discipline

Chemistry is a fundamental science and an instrument of research and knowledge of processes occurring
in living systems. It forms the basis for studying the functioning of biological systems of different levels
of organization at the molecular level.
The course includes selected topics of general and organic chemistry and their relationship with the
processes occurring in the human body: chemical thermodynamics and kinetics. Enzymatic catalysis.
Solutions and their colligative properties. Protolytic theory and buffer systems. The structure of matter.
Complex compounds, biogenic elements. Redox systems. Superficial phenomena. Dipers systems.
Heterofunctional compounds: hydroacids, oxo acids, amino alcohols. α-amino acids. Peptides. Proteins.
Solutions of biopolymers. Carbohydrates. Heterocyclic compounds. Alkaloids. Nucleosides. Nucleotides.
Nucleic acids. Saponifiable and unsaponifiable lipids.
Learning outcomes of the course unit

It is expected that upon completion of this program the student:
- will be able to use the principles of chemistry (rules, laws, patterns) to characterize the structure and
functions of the human body and use in medical practice
- will be able to characterize the chemical composition of the main structures of the human body (body
fluids, organic compounds) and correlate them with the properties of these structures (heterogeneity, acid-
base properties, buffer properties, etc.)
- will have an idea of the most important biochemical processes and various types of homeostasis in the
body;
- will be able to characterize the influence of factors on the shift of equilibrium in chemical systems,
equilibria in the body;
- will be able to characterize the influence of factors on the shift of equilibrium in chemical systems,
equilibria in the body
- will be able to perform basic calculations using the necessary scientific information
Redaction: 1
- will be able to critically comprehend and discuss data of calculations and studies
The study of this discipline is based on knowledge of the following disciplines:

chemistry, physics, mathematics, biology (school course)
Plan for studying the discipline

Contact work Self-study work
hours * hours
№ Topic Prac Labs Consulta Self-
tical tions study
lesso
ns
1. Macro- and microelements: biological role, medical 4 1 3
applying
2. Elements of chemical thermodynamics and kinetics. 4 1 3
Enzymatic Catalysis and Chemical Equilibrium
3. Solutions: composition and colligative properties. Osmotic 4 2 3
phenomena in biological systems
4. Protolytic equilibria and processes. Buffer solutions 3 1 3
5. Heterogeneous and metal-ligand equilibria. Complex 4 1 3
compounds.
6. Physico-chemistry of surface phenomena. Chromatography 4 1 3
7. Physico-chemical properties and stability of disperse 4 1 3
systems
8. Redox reactions and equilibrium. Electrodes` potential. 4 2 2
Midterm №1
9. Fundamentals of the structure and reactivity of organic 4 2 3
compounds. Reactivity of alcohols, phenols, thiols, amines.
10. Reactivity of aldehydes, ketones, carboxylic acids. Amino 4 2 3
alcohols, aminophenols, phenolic acids, hydroxy- and oxo-
acids
11. Amino acids. Biologically important properties of α-amino 4 1 3
acids. Peptides. The structure and properties of protein
molecules. Biopolymer solutions.
12. Carbohydrates. Monosaccharides. Disaccharides. 4 1 3
Polysaccharides
13. Saponifiable and unsaponifiable lipids 4 1 3
14. Heterocyclic compounds. Nucleosides, nucleotides. Nucleic 4 1 3
acids
15. Metabolic reactions of biologically active compounds. 4 2 2
Midterm №2
In total 60 20 40
POLICY of ASSESSMENT
Your final assessment by discipline will consist of two parts of the current (admission rating, 60%)
and final control assessment (40%).
The admission rating is set based on the total value of the current control assessments received at 3, 5,
7, 10, 12, 14 weeks (40%), and the midterm control received at 8, 15 weeks (60%). You are admitted to
the final exam if you have scored a total of at least 50% during the semester. The final assessment is set
on the basis of the total value of the admission rating (60%) and the Final Control Assessment (40%) -
exam
If you do not agree with the exam result, you have the right to appeal the review of the assessment.
The procedure is in accordance with the adopted Regulation on the appeal.
Type of % Learning Outcome Assessment Forme

control Framework
Current 40% of Written (MCQ test,
control admission CCA= written assignments)
assessments rating Current control provides
(CCA) for the assessment of
theoretical knowledge,
practical skills of a
student in practical
3, 5, 7, 10, 12, 14 weeks classes and is carried out
(6 of them) by a written survey, work
in small groups, by the
TBL method. It is carried
out in the time specified
in the matrix of
assessments of results for
the discipline.
Midterm 60% of MM= Written (written
(MM) admission assignments)
rating
Midterm №1 – lesson №8
Midterm № 2 – lesson №15.
Admission AR = AR = The minimum score of
rating (AR) (CCA*0.4) + admission rating for
(MM*0.6) admission to the exam =
50. Students who do not
score 50% of the
admission rating are not
allowed to take the
discipline exam.
Exam E*0.4 The exam in discipline is
held on tickets, in
writing.
Final FA= The minimum score of a

assessment (AR*0.6)+ positive FA in the
(FA) (E*0.4) discipline = 50.
If a student receives 25-
49 points in an exam (FX
score), he has the right to
retake the exam during
the interim certification
period.
A student who does not
agree with the exam
result has the right to
appeal no later than the
next day after passing the
exam.
The matrix of learning outcomes assessment by discipline
Assessed Learning Outcomes

Topic Lesson Knowledge Practical Communic Consul Self-study Midterm
№ № (different skill ation skills tation
cognitive
level)
1 1
2 Assessment: Assessment:
Formative Questions are
(in the form included in
of feedback; the tickets for
can be the topic
improved) assessment
and midterm
Summative, set Questions are
on the basis of included in
solving the tickets for
problems/cases the topic
(practical skills assessment
1, 2, 4) and midterm
2 4 Assessment: Assessment:
can be the topic
and midterm
1, 2, 3, 4) and midterm
can be the topic
and midterm
Formative Summative
(in the form (written control,
of feedback; set on the basis
can be of solving
improved) problems/cases)
can be the topic
and midterm
can be the topic
and midterm
can be the topic
and midterm
Formative Summative
(in the form (written control,
of feedback; set on the basis
can be of solving
improved) problems/cases)
Formative assessment does not appear in the electronic journal. This is a constructive feedback
following the results of a practical lesson.
Summative assessment is published in an electronic journal. It set on the basis of solving problems/cases
The list of tasks to achieve the learning outcomes:
List of practical skills

1) qualitatively and quantitatively characterize the processes occurring in a living organism, using the
laws and rules of chemistry
2) characterize the chemical composition, structure and properties of the main compounds of the
human body
3) evaluate the influence of various factors on the equilibrium shift in the system, as well as the
relationship of the structure and properties of compounds
4) demonstrate the ability to learn, to self-study and professional development
Recommended literature:
Main/basic literature
1. Morris Hein, Scott Pattison, Susan Arena. Introduction to General, Organic, and Biochemistry [Text]:
Book / 10th Edition.-USA: John Wiley&Sons, Inc, 2012.-1091 p.
2. Theodore L.Brown, H.Eugene LeMay Jr., Bruce E.Bursten, Catherine J.Murphy, Patric M.Woodward,
Matthew W.Stoltzfus. Chemistry. The Central Science [Text] / 13 Edition.-published by Pearson
Education Limited.- 2015.- 1140 p.
Additional literature
1. Ira, B. General, Organic, and Biochemistry - [Electronic resource]: / Blei Ira.- Second edition.- New
York: W. H. Freeman and Company, 2006.- 787 с.
2. Physical Chemistry. P.Atkins. 2007
3. Organic chemistry. R.Th.Morrison. 2007
4. Electronic resources
 http://www.chemistry.wustl.edu/~edudev/LabTutorials/
 http://www.chemguide.co.uk/
 https://chem.libretexts.org/Demonstrations_and_Experiments
 https://www.chemistryworld.com/careers/the-future-of-medicine/4891.article
 https://chem.libretexts.org/Core/Physical_and_Theoretical_Chemistry
The list of tasks to achieve the final learning outcomes:
Lesson №1
Macro- and microelements: biological role, medical applying
After the lesson the student will be able to:

- classify the elements
- write down the structure of the electron shell of atoms and ions of elements
- characterize the biological role of biogenic s-, p-, d-elements
- illustrate the use of compounds of biogenic elements in medical practice
- identify and characterize types of bonds between atoms in compounds
Bibliography
Required reading:
Electronic resources
Recommended reading :
Questions of the lesson:

1. Biogenic elemets. Classification of biogenic elements.
2. Endemic diseases: causes, methods of prevention.
3. Biogenic s-, p-, d- elements, their biological importance and use of their compounds in medicine..
4. Types of chemical bonds and their main characteristics. Van der Waals forces.
5. Characteristics of the structure of the electron structure of atoms and ions, their influence on the types
of bonds formed.
6. The relationship between the structure of molecules and the biological activity of substances.
7. Effect of toxic metals on human health.
8. Radioactive elements used in medicine. Biological effect of radiation.
Class format: Discussion of tasks and situational tasks.

Assessment: Formative (in the form of feedback; can be improved)
Tasks and exercises for discussion on practical lessons:
First, organizational issues and discipline policies are discussed..

Assessment of the level of residual knowledge of the school chemistry course is carried out (no grade is
set).
1. Place the given elements in the groups (one and the same element can belong to several groups):
K, Na, P, C, Mn, S, O, I, Mg, Pb, Fe, Ca, H, Hg, Cl.
Organogens Macroelements Microelements “Metals of life” Toxic elements
(trace elements)
2. Write down the structure of the electron configuration of the atom and ion of (a) sodium and (b)
chlorine. Which of radiuses is a larger one In (a) and (b) cases? Why?
3. *Compare the radii of sodium and potassium ions. In which case will the charge density be
higher? Which ion will be more hydrated?
4. What is necessary for hydrogen bonds formation? From the following, select the compounds
which could form hydrogen bonds HI, H2S, H2O, HCl, HF, NO2, ethanol, dimethyl ether. Show
these bonds schematically.
5. There is usually a lack of iodine in foods in mountainous areas. What could this lead to? What are
the diseases of this type called? What measures can be taken to prevent them?
6. What types of chemical bonds occur in the molecules of following substances: iron, water, sodium
chloride, oxygen, argon, ammonium chloride, potassium carbonate.
7. Give examples of macroelements, microelements, organogens. Describe their biological role.
What are the main intracellular and extracellular ions.
8. Why is strontium ion antagonist to calcium ion? How does the radioactive isotope strontium-90
affect the human body?
9. Describe the biological importance of halogen ions: fluorine, chlorine, bromine, iodine. Medical
use of their compounds.
10. The biological importance of calcium. Diseases caused by its deficiency and excess.
11. Which ions cause osmotic pressure of blood? What elements form the basis of bone tissue?
12. The biological role of metal ions (iron, zinc, magnesium, cobalt, etc.). How does the effect of
excess and lack of these elements?
13. Give examples of elements that have a toxic effect on a living organism. How do they appear in
nature? What is their toxic effect expressed in?
Tasks and exercises for self-study which could be discussed during a consultation:
1. Fill in the gaps in the following table, assuming each column represents a neutral atom
Symbol 52Cr
Protons 25
Neutrons 30 64
Electrons 48
Mass no.
2. Write the elecrton configuration for the following ions , and determinate which have nobel-gas
configurations: К+, Cl-, Mg2+, S2-, Cr3+, N3-.
3. What types of chemical bonds occur in molecules of the following substances: Cu, KBr, H2SO3, I2,
Na2SO4.
4. Give examples of compounds whose molecules are bound by van der Waals forces.
5. Give the definitions of the concepts of synergism and antagonism of elements. Give examples of
compounds used in medical practice.
6. Give examples of diseases that can be caused by an excess or deficiency of any elements in the
body.
7. How could the deficiency of biogenic elements' ions be filled in the body? Give examples.
8. Describe the toxic effects of Hg, Pb, Cd and other heavy metals..
Assessment: in the form of feedback during the consultation

Questions for self-study: Present in tabular form a brief description of the biological significance of the
following elements: K, Na, Ca, Mg, C, N, P, S, O, F, Cl, Br, I, Cu, Fe, Zn, Mn.
Assessment: Questions are included in the tickets for the topic assessment and midterm.
Lesson № 2
Elements of chemical thermodynamics and kinetics.

Enzymatic Catalysis and Chemical Equilibrium

- calculate the energy characteristics of processes and predict the direction of spontaneous processes
- describe the chemical transformations in time using kinetic curves and kinetic equations
- predict the effect of the change of concentration of reagents, temperature, catalysts or pH on the
reaction rate
- characterize the equilibrium of processes and the influence of various factors on the equilibrium
- characterize the features of enzymatic catalysis and analyse Michaelis-Menten equation
- use the reference literature to find the values necessary for calculations
Bibliography
Required reading:

1. The first law of thermodynamics (the law of conservation of energy). The thermal effect of a
chemical reaction. Thermochemical equations. Enthalpy. Lavoisier and Laplace’s law of
thermochemistry. Hess’s law.
2. The second law of thermodynamics. Entropy. Gibbs free energy as a main criterion for the
spontaneity of processes. The enthalpy and entropy factors.
3. Features of the thermodynamics of living systems. Characteristic of the stationary state of a
thermodynamic system. The Prigogin’s principle.
4. The rate of chemical reaction. Factors affecting the reaction rate.
5. Molecularity and order of reaction. Determination of the reaction order. Kinetic equations and
kinetic curves for reactions of various orders
6. The half-reaction time. The dependence of the half-reaction time of concentration for reactions of
the zero and first orders. Half life time.
7. Dependence of the reaction rate on temperature. The Van't Hoff's rule. The Arrhenius equation.
Activation energy.
8. Enzymatic catalysis. The Michaelis-Menten equation, its analysis. Order of enzymatic reaction in
respect to substrate and enzyme.
9. Features of enzymatic catalysis. Influence of temperature and acidity of the medium on
biochemical reactions.
10. Principle of Le Chatelier. Shift of the chemical equilibrium with a change in the concentrations,
temperature, pressure. The principle of adaptive rearrangements.

1. Place the given thermodynamic systems into the corresponding groups (the same system can
belong to several groups): a bowl with boiling water; closed can with soup; thermos with coffee;
universe, sugar tea, alive dog, plant, human.
Open Closed Isolated Homogeneous Heterogeneous
thermodynamic thermodynamic thermodynamic thermodynami thermodynamic
system system system c system system
2. The thermal effect of the water formation reaction is 286 kJ. What will be the thermal effect of its
decomposition? Why?
3. Calculate the heat of the reaction of glucose fermentation: С6Н12О6(g) → 2С2Н5ОН(l) + 2СО2(g). Use
the reference table to find the required values. Is this reaction exothermic?
4. Calculate the standard entropy of the reaction 2C 2H5OH(l) → С2Н5ОС2Н5(l) + Н2О(l). Use the
reference table to find the required values.
5. *How does the energy of the system change for exothermic and endothermic reactions? Illustrate
your answer graphically. Indicate the activation energy.
6. * Are these processes spontaneous or nonspontaneous at the standard conditions:
а) 2N2(g) + O2(g) ↔ 2N2O(g); ΔH0298>0;
b) 2C(s) + O2(g) ↔ 2CO(g); ΔH0298<0.
Explain why.
7. *For which of the reactions:
а) 3C2H2(g) ↔ C6H6(l); ΔH0r<0; ΔS0r<0;
b) FeO(s) + H2(g) ↔ Fe(s) + H2O(g); ΔH0r>0; ΔS0r>0
probability of being spontaneous decreases with decreasing of temperature? Explain why.
8. Suggest two possible ways to calculate the Gibbs energy for a reaction 2СО(g) + О2(g) →
2СО2(g). Use the reference table to find the required values. Is this reaction spontaneous under
standard conditions?
9. ATP formation from ADP and H2PO4-is nonspontaneous process. This reaction is connected with
creatine-phosphate hydrolysis which has negative ΔGo value:
ADP + H2PO4- ATP + H2O; ΔGo = +30 kJ
Creatine-phosphate + H2O  creatine + phosphate; ΔGo = -43 kJ
Use principle of thermodynamic conjugation to prove the possibility of spontaneous process in
the body: Creatine-phosphate + ADP  Creatine + ATP
10. What is the difference between average and instantaneous reaction rates? How are these values
calculated??
11. Explain the differences between: (a) molecularity and order of the reaction ; (b) overall order of
the reaction and the order with respect to the reactants.
12. How many times the rate of a bimolecular reaction decrease when a reagent concentration
decrease in twice?
13. Calculate how the rate of a chemical reaction А(s) + 2В(g) = 2С(s) will change when the
pressure is doubled if the kinetic equation of this reaction: v = k CB2 ?
14. The reaction H2O2 + 2HI → I2 + 2H2O is characterized by the first order in respect to both
reactants. Calculate the initial rate of the reaction if the same volumes of 0.02 M Н2О2 and 0.05 M
HI solutions were mixed. The rate constant is 0.05 L/(mols).
15. * The table shows the results of a hypothetical reaction 3А + В → 2С + 2D study (at constant
temperature):
№ of the experience Initial concentration, mol/L Initial rate of the
reactant А reactant В reaction, mol/(Ls)
1 0,02 0,02 0,04
2 0,04 0,02 0,16
3 0,02 0,04 0,04
Determine the reaction order with respect to substance A and substance B; calculate the value of
the reaction rate constant.
16. The appearance of the isotope of iodine (131I) occurs during accidents at nuclear power plants. Its
half-life is 8 days. How long does this isotope decay to 99%
17. The temperature coefficient of the reaction is equal to 2.4. This reaction ends per 30 minutes at
100°C. Calculate the time required to complete the reaction: a) at 80°C; b) at 130°C.
18. In what direction the equilibrium of reaction shift СО2(g) + С(s) ↔ 2СО(g), ΔН=171 kJ; if
temperature increases?
19. *The poisonous phosgene gas is produced from СОand Cl2. The equilibrium in the system Cl2(g)
+ CO(g) ↔ COCl2(g)established whenreact 80% of СО. Calculate the value of the equilibrium
constant for this process, if it is known that the initial concentration of CO, Cl 2and COCl2are equal
to 2; 2 and 0 mole/l respectively
1. Give examples: (a) open, closed and isolated systems; (b) homogeneous and heterogeneous systems.
Explain why you take them.
2. Determine the standard enthalpy of urea hydrolysis reaction CO(NH 2)2 (solution) + H2O (l) = СО2 (solution) +
2NH3 (solution) . Is this reaction exothermic or endothermic?
Substance and its aggregate state ΔНo, 298.15
kJ/mole
СО(NH2)2(solution) -319,2
NH3(solution) -79,9
СO2(solution) -413,6
H2O (l) -285,8
3. Calculate the entropy of reaction CO(g) + 2H2(g)  CH3OH(g), if the standard entropy of gaseous
hydrogen, carbon monoxide and methanol are respectively 131, 198 и 240 J/(mole.K).
4. In the human body, ethanol is oxidized in two stages: at first to acetaldehyde (ΔН01= -256 kJ/mol), then
to acetic acid (ΔН02= -237 kJ/mol): С2Н5ОН → СН3СОН → СН3СООН. Calculate thermal effect of
oxidation reaction: С2Н5ОН → СН3СООН.
5. Calculate the standard Gibbs energy of the denaturation reaction of trypsin 50 оС, standard enthalpy and
standard entropy of reaction are, respectively, 283 kJ/mol and 288 J/(mol.K). Characterise the
contribution of enthalpy and entropy factors.
6. Dinitrogen monoxide N2O is used in medicine for anesthesia. Calculate the Gibbs energy of the
reaction of oxidation of dinitrogen monoxide (N 2O) into toxic nitric oxide (NO) by atmospheric
oxygen and to conclude whether possibility of this process take place. The values of the Gibbs free
energy for gaseous substances dinitrogen monoxide (N2O), nitric oxide (NO) and oxygen are,
respectively, 103.7; 87.6; and 0 kJ/mol.
7. How does the rate of reaction change 2NО(г) + O2(г) ↔ 2NО2(г), if: а) the pressure in the system
increases 3 times; b) the volume of the system decreases 2 times?
8. Give the kinetic equation and show graphically, how the reaction rate depends on the concentration
for: a) the zero-order reactions; b) the first-order reactions; c) second-order reactions.
9. Write down the kinetic equation of reaction FeCl 3 + 3KNCS ↔ Fe(NCS)3 + 3KCl, if the reaction has
the first order with respect to both reactants.
10. The half-life of some first-order reaction is 30 minutes. What part of the initial concentration will
remain in an hour?
11. How the rate of reaction change by the temperature rises on 30 degrees, if the temperature coefficient
is equal to 2.8.
12. In what direction the equilibrium of reaction shift СО32- + Н2О ↔ НСО3- + ОН-, if alcali solution is
added to this solution?
Questions for self-study: Give examples of the use of radioactive substances in medical practice. What
are the half-lives of these substances? How long are they excreted from the body?
Lesson №3
Solutions: composition and colligative properties.

Osmotic phenomena in biological systems

- calculate different types of concentrations and recalculate one of them into another one
- quantitatively characterize the colligative properties of non-electrolytes and electrolytes
solutions
- illustrate the role of osmosis in living systems (turgor, hemolysis, plasmolysis, deplasmolysis,
osmolarity and osmolality of biological fluids);
- show a use of cryometry, ebulliometry and osmometry methods in determination of the molar
mass of the solute in biomedical research
- calculate the degree of dissociation and the isotonic coefficient of the electrolyte in solution
knowing its colligative properties
Bibliography
Required reading:

1. Water as an universal solvent. Aqueous solutions in the living body.
2. Expression solution concentration: Mass fraction, molarity, normality (molar concentration of
equivalent), molality, titer of solution, mole fraction.
3. Diffusion. Biological role of diffusion.
4. Colligative properties of nonelectrolytes solutions.
5. Vapor pressure lowering. Boiling point elevaton. Freezing point depression.
6. Osmosis. Osmotic pressure. The Van't Hoff law. Osmolarity and osmolality of the solution.
7. Osmosis in biological systems. Oncotic pressure. What is isotonic solution? Give examples of
solutions which are isotonic to the blood plasma.
8. Hypertonic and hypotonic solutions. How could hypertonic solutions be used in medical practice?
What happens to the cell in hypotinic and hypertonic solutions? Give definitions of hemolysis,
plasmolysis, deplasmolysis.
9. Features of the colligative properties of solutions of electrolytes. Explain the physical meaning of the
isotonic coefficient (Van't Hoff coefficient). How is it calculated?
10. Determination of molar mass of solute from colligative properties.

Assessment: Summative, set on the basis of solving problems/cases (practical skills 1, 2, 4)

1. When insufficient gastric acidity dilute hydrochloric acid is used with a mass fraction of HCl 8%.
Calculate the mole fractions of HCl and water in this solution.
2. How many grams of solute are contained in a given volume of solution: a) 200 ml of a 0.3 M glucose
solution; b) 400 ml of 0.15 n NaCl solution.
3. Calculate molarity of 38% HCl solution (dencity of the solution is 1.19 g/mL).
4. 5% glucose solution (M (C6H12O6) = 180 g/mol) is used to replenish fluid in the body and as a source
of easily digestible carbohydrate. Calculate molarity and molality of this solution (ρsolution=1.02 g/ml).
5. Calculate the molarity and molality of the 47% ethanol aqueous solution. The density of the solution
is 0.92 g/ml. What are mole fractions of alcohol and water in this solution?
6. * Is the process of dissolution of potassium chloride in water spontaneous at 25 оС, ifΔHo = 17,2
kJ/mole; ΔSo = 75,7 J/(mole.К)?
7. The normal osmotic pressure of blood plasma is 740–780 kPa. Calculate osmolarity of the plasma at
310 K.
8. * How does the freezing point of sucrose solution change, if you add to this solution: a) water; b)
urea. Explain your answer.
9. * There are two solutions with the same molarity - urea and calcium chloride. Which of these
solutions has higher osmotic pressure (at the same temperature). Explain your answer.
10. * Dilute solutions of sucrose and glucose have the same mass fraction of water. Which of these
solutions will boil at a higher temperature? Explain your answer.
11. * Enzymatic hydrolysis of the dipeptide take place in the solution. How will osmotic pressure of this
solution vary in time?Explain your answer.
12. *Aqueous solutions of urea and sucrose are separated by a semipermeable membrane. There is no
solvent transfer through the membrane. Which of the solutions has greater value of mass fraction of
solute? Explain your answer.
13. *0.5 mol of sucrose and 0.2 mol of calcium chloride were dissolved In equal volumes of water. The
freezing points of both solutions are the same. What is degree of dissociation of calcium chloride in
the solition??
14. Calculate the mass of sodium chloride that must be added per kilogram of ice so that it melts at –5°C.
The degree of salt dissociation in this solution is 90%.
15. * 9 g of sodium chloride (M = 58.5 g / mol) and 1 g of glucose were dissolved in 1 l of water.
Calculate the osmolality of this solution.
16. In humans, the osmolarity of the interstitial fluid increases from 0.3 osmol/l in the cortex to 1.2
osmol/l in the papilla of the nephron. Calculate the variation of osmotic pressure.
17. Osmotic pressure of 0.01 M CHCl2COOH solution at 300 K is equal to 43.59 kPa. Calculate degree
of dissociation of dichloroacetic acid in the solution?
1. Calculate the weight of the solute and the weight of water needed for preparing: a) 750 g 15% HCl
solution; b) 200 ml 0.01 М KMnO4; в) 250 ml 0.2 NСаCl2 (density of dilute solutions is equal to1 g/ml).
2. Calculate the mole fraction and mass fraction of sodium chloride in a system consisting of 0.2 mol of
NaCl and 8 moles of water.
3. The potassium chloride solution (ρ = 1.13 g / ml) contains 245.7 g of salt in 1000 g of water. Calculate
molality, molarity and mole fraction of salt in the solution.
4. What are the molality and mole fraction of solute in a 67% sucrose solution?
5. Potassium chloride solutions are used in medicine in case of hypokalemia, digitalis intoxication nad
arrhythmia of various origins. Calculate the molarity, molality and mole fractions of potassium chloride
solution contains 245.7 g of salt in 1000 g of water (ρ = 1,131 g/ml).
6. Adrenaline is used in medical practice in the form of solutions. The ampoule contains 1 ml of a 0.1%
solution (ρ = 1 g/ml). Calculate the molar concentration of adrenaline in this solution and the mass of
adrenaline in 1 ml of the solution (Madr = 219.7 g/mol)
7. Calculate the freezing point of solution which is prepared by dissolving of 2.76 g glycerol in 200g of
water?
8. Calculate the molecular weight of nonelectrolyte which is prepared from 5g of solute and 500g of
water if freezing point lowering is equal to 0.102.
9. What weight of sucrose should be dissolved in 250 g of water to obtain a solution with the boiling point
at 100.2oC?
10. Calculate the osmotic pressure of the solution which contain 1.34g of deoxyribose in 0.1 liter of
solution at the temperature 37oC. Is this solution hypo-, hyper- or isotonic with respect to a following
solutions with osmotic pressure: a) 780 kPa ( blood, upper bound); b) 730 kPa (blood, lower limit); c) 258
kPa.
11. Solution contains 34.23g of sugar dissolved in 45.05g of water. Calculate the vapor pressure of
solvent above these solution (Psolvent) if the vapor pressure of the pure solvent (P osolvent) is equal to
2.5∙104Pa.
12. Freezing point of the blood plasma is –0.59°C. What is the osmolality of plasma and what is its
osmotic pressure at 37°C? (Density is assumed to be 1 g/ml).
13. 0.9% sodium ckloride solution is isotonic to blood plasma. The density of this solution is 1.005 g / ml.
Calculate the isotonic coefficient (van't Hoff coefficient) and degree of dissociation of sodium chloride in
such a solution, if the osmotic pressure of the blood iis assumed to be 745 kPa.
Questions for self-study: Give examples of the use of isotonic and hypertonic solutions in medical
practice. What are concentrations of these solutions? What is the principle of their action?
Lesson №4
Protolytic equilibria and processes. Buffer solutions

- calculate the pH of acid solutions of acids, bases and buffer solutions
- explain the essence of the mechanism of the buffer action on the example of the buffer systems
of the body
- calculate the pH value in buffer solutions of known composition and the buffer capacity of the
solution
- explain the essence of acid-base homeostasis and the mechanism of its maintenance in the body
- characterize the state of acidosis and alkalosis as pathological conditions of the body
- use the reference literature to find the values necessary for calculations
Bibliography
Required reading:

1. Strong and weak electrolytes. The degree of dissociation; constant of dissociation. Ostwald’s
Dilution Law. Brønsted–Lowry theory.
2. The degree of dissociation and constant of dissociation. Ostwald's law.
3. Ionic product of water. pH as a characteristic of acidity of the solution.
4. Calculation of the concentration of hydrogen ions and hydroxide ions in solutions of strong and
weak acids and bases.
5. Electrolytes in vivo. Examples of pH values of various fluids of the human body. Acidic-basic
homeostasis of the living body.
6. Buffer solutions. The mechanism of the buffer action of ammonia, bicarbonate, protein and
phosphate buffer systems.
7. Calculation of pH of buffer solutions (Henderson-Hasselbach equation).
8. Buffer capacity. Factors affecting the buffer capacity of the solution.
9. Buffer of the blood, their biological role. Comparative characteristic of the blood buffer
systems.
10. Acidosis. Alkalosis. Causes and solutions


1. Calculate concentration of hydroxide-ions [OH-], when concentration of hydrogen-ions [H+]
(mole/l) is equal to: (a) 2∙10-3; (b) 3.2∙10-7. Are these solutions basic?
2. *Calculate the pH of the solution to 10 liters which contained 3.7 g of potassium hydroxide.
3. *How will the pH of solution change when 30 ml of 0.2 M sodium hydroxide solution is added to
300 ml of water? Write calculations.
4. Calculate molar concentration of formic acid, if its degree of dissociation in the solution is 0.05,
and constant of dissociation is Kа= 2.1.10-4.
5. *Aqueous solution of boric acid is used as an external antiseptic. Calculate the degree of
dissociation of boric acid for the first step, if 12.4 g of the acid is contained in 2 liters of solution
(Ка = 5.8∙10-10).
6. Calculate pH of buffer solution which was prepared by mixing of 250 mL of 0.2M formic acid
and 100 mL 0.5M sodium formate. (Ка(НСООН) = 1.8·10-4)
7. *What is the pH of the buffer solution containing 0.1 mol of NH4OH and 0.1 mol of NH4Cl in 1
liter of solution (pK (NH4OH) = 4.75)? How will the pH change when solution would be diluted
10 times?
8. *Calculate the volumes ratio of 0.1M solutions of sodium dihydrogen phosphate and sodium
hydrogen phosphate to prepare a buffer solution with pH 6.73.
9. 0.52 ml of a 1M NaOH solution was added to 10 ml of acetate buffer to change the pH by one.
Find the buffer capacity (mol / Led.rN) of this buffer solution.
10. *To 10 ml of a 0.1M solution of sodium formate was added 5 ml of 0.05 M hydrochloric acid
solution. Is the resulting solution buffer? Explain your answer with calculation.
11. *Calculate the pH of the acetate buffer solution prepared from 100 ml of 0.1 M CH 3COOH and
200 ml of 0.2 M CH3COONa (Kа(CH3COOH) = 1.7510–5). How will the pH of this buffer
solution change when 30 ml of a 0.2 M NaOH solution is added to it? Explain the answer with
calculations..
12. *Determine the pH of the buffer solution containing 18.4 g of formic acid and 68 g of sodium
formate in 1 liter if pK (HCOOH) = 3.75. How will the pH change when the solution is diluted 50
times? Explain the answer with calculations..
13. Explain the mechanism of action of the following buffer solutions: (a) bicarbonate, (b) protein, (c)
phosphate, (d) ammonia buffer systems. What is biological role of these systems in the normal
functioning of the body?
14. *40 ml of a 0.04 M NaH2PO4 solution were added to 16 ml of a 0.1 M Na 2HPO4 solution.
Determine: (a) the pH of the resulting buffer solution (K a(H2PO4-) = 1.6×10–7; (b) how the pH of
this solution changes when 6 ml of a 0.1 M HCl solution is added to it; (c) the possibility of
preparing phosphate buffer solution with pH = 8.5.
1. Put the given compounds in the table according to the protolytic theory (the Brønsted-Lowry
theory): HCl, CO32-, NH4+, SO42-, NH3, OH-, H2O, H2CO3, HSO3- :
Acids Ampholytes Basis
2. Calculate concentration of hydrogen-ions [H+], when hydroxide-ions concentration [OH-] (mole/l) is

equal to: (a) 4∙10-10; (b) 5∙10-6. c) 3.2∙10-7. . Are these solutions acidic?
3. Calculate pH of gastric juice if its active acidity is equal to 0.04 mole/l.
4. The range of changes in proton concentration for living organism is 1 .10-7 ÷ 1.6.10-8mole/l. What are
the values of pH corresponding to this state?
5. Write down (a) the dissociation equations for phosphoric acid in three steps and (b) the dissociation
constant expression for each of them. Values of these constants are equal to 7,52·10-3; 6,31·10-8;
1,26·10-12 respectively. How strength of these acids could be characterized?
6. Calculate degree of dissociation  for weak monobasic acid if concentration of its solution is 0.1
mole/L and constant of dissociation Ка is 10-9.
7. Calculate constant of dissociation Kb of weak monoacidic base if concentration of its solution is 0.2
mole/L and degree of dissociation =0,05.
8. Explain the mechanism of the buffer action on the example of acetate buffer solution and ammonia
buffer solution.
9. Calculate pH of a buffer solution containing 3.6 ml of 0.2 N solution of ammonium chloride and 2.3
ml of 0.1 N ammonium hydroxide solution (Kb=1.79·10-5).
10. 18 ml of 0.1 N hydrochloric acid solution was added to 100 ml of blood to change the pH from 7.36
to 7.00. Calculate the buffer capacity of the blood on the acid.
Questions for self-study: Characteristics of the biological role and mechanism of action of buffer
systems in the human body: protein, bicarbonate, phosphate, hemoglobin, oxyhemoglobin and ammonia.
Lesson №5
Heterogeneous and metal-ligand equilibria. Complex compounds

- describe the equilibrium of the system using equilibrium constants
- calculate the equilibrium concentration of ions in solution
- apply the Le Chatelier principle to consider acid-base, heterogeneous equilibria and equilibria
in solutions of complex compounds
- characterize the effect of common ions on the equilibrium in the system
- describe the main types of equilibria and show the possibility of the combined equilibria and
competing processes in the process of life
Bibliography
Required reading:

1. Heterogeneous equilibrium. Solubility constant. Quantitative characteristic of heterogeneous
equilibria.
2. Factors affecting the formation of sediment. Conditions for the formation and dissolution of
precipitation.
3. The effect of the pH of the solution and the addition of the ion of the same name on the solubility
4. Heterogeneous equilibria in the human body. Hydroxyapatite.
5. The structure of complex compounds. Isomerism and nomenclature of complex compounds.
6. Stability of complex compounds. Instability and stability constants of complex ions.
7. Polydentate ligands. Formation of complex compounds with polydentate ligands.
8. Complex compounds of a living organism.
9. Complexons, their use in medicine.

Assessment: Summative, set on the basis of solving problems/casesи тд (Practical skills 1,2,4)

1. Give an example of a heterogeneous equilibrium. What processes take place in the system in a
state of heterogeneous equilibrium?
2. Calculate the solubility of barium sulfate (mol/L) if the solubility constant of this compound is
1.110-10.
3. Calculate the solubility of CaF2 in water (mol/L and g/L) if Ks(CaF2) = 3.9.10-11.
4. The molar solubility of gold(I) chloride is 4.510-7 mol/L. Calculate the solubility constant of this
compound.
5. Calculate the mass of lithium carbonate in 3 liters of its saturated solution. The solubility constant
of this compound is 4.0·10-3.
6. 144 ml of a saturated solution of sodium periodate NaIO 4 contains 1 gram of iodine. Calculate the
solubility constant of this salt.
7. The solubility of nickel (II) oxalate is 3 mg/L. Calculate the solubility constant of this salt.
8. Calculate the mass of calcium ions containing in a 350 ml saturated solution of calcium oxalate.
KS(СаC2O4)=2.310-9.
9. Strontium oxalate precipitate is in contact with a 0.05 M solution of ammonium oxalate. Calculate
the mass of strontium oxalate contained in 0.3 liter of this solution. KS(SrC2O4)=1.610-7.
10. The toxicity of barium ions is manifested at concentrations above 4 mg / L. Prove that barium
sulfate may be used as a radiocontrast substance in medicine (K s=1.0.10-10). Can barium hydroxide
(Ks=5.0.10-3) be used for this purpose?
11. When you receive iodine drugs iodide ions are allocated through tear glands. For the treatment of
acute conjunctivitis 2% silver nitrate solution (ρ = 1 g/ml) is used. Calculate concentration of
iodide ions, at which there is a risk of formation of crystals of silver iodide (cauterizing action).
12. *Explain why silver chloride dissolved in ammonia solution but silver amminocomplex can be
destroyed with potassium iodide? Constants solubility chloride and silver iodide are, respectively,
1.78.10-10 and 8.3.10-17.
13. What are the features of the structure of the electron shell of the atoms of complexing agents?
14. Give examples of complex compounds that are found in living organisms. Describe the structural
features of metalloenzymes and other biocomplexes (hemoglobin, chlorophyll, etc.).
15. What are chelates? Describe the use of chelates in medicine. What explains the toxicity of heavy
metal salts? What compounds are used as antidotes for poisoning with heavy metal salts?
16. Describe the following complex compounds according to scheme: (a) the central atom (ion-
complexing agent), its oxidation state and coordination number; (b) ligands and their dentality; (c)
equations of primary and secondary dissociation; (d) an expression for the instability constant.
Complex compounds: (1) K2[Ni(CO3)2(H2O)4]; (2) [Cu(NH3)4](NO3)2; ); (3)
diaquatetraamminenickel (II) nitrate; (4) diammindichloroplatinum
17. *Cobalt ion Co2+ could form complex compounds with different ligands. Which of them – NH3 or
SCN- – could form more stable complex ion? Write the formulas of complex ions, the equations of
their dissociation and the expression for the instability constant. The values of the instability
constants find in the table.
18. *Compounds ethylenediaminetetraacetate (EDTA) and its salt Trilon B (Na2H2T) are commonly
used as ligands in medical and analytical practice. Which of the following cations forms the least
stable complex compounds with this ligand: Со3+ (Кin=3∙10-41), Мg2+ (Кin=8∙10-10), Fе 2+ (Кin=6∙10-
15
), Fе3+ (Кin= 6∙10-25)? Place the complexes in order of decreasing of their stability.
19. *Which of the complex compounds of iron-ion Fe2+ - with glycine or histidine as bioligands - is
more stable? Instability constants of complex compounds are, respectively, 1,58.10-8и 5,0.10-10.
20. *Write the equation of the secondary dissociation of diamminedichloroplatinum. What factors can
influence the equilibrium position of this reaction? What happens when sodium chloride solution
is added to this solution? When ammonia is removed from solution?
1. Compare the concepts of ionic product and solubility product (solubility constant).
2. Solubility constant (solubility product) of AgSCN is equal to 1.1 .10-12. Calculate the solubility of the
compound in water (mole/l).
3. How the concentration of ions change in solution if 0.1 mol NaCl is added to 1 liter of a saturated
solution of AgCl (Ks=1.10-10)?
4. Solubility of magnesium hydroxide at 18оС is equal to 1.7.10-4 mole/l. Calculate solubility constant
(solubility product) of Mg(OH)2 at this temperature.
5. What volume of water required for complete dissolution of 1 mg of HgS (Ks=1,6.10-52)?
6. Calculate pH value when Ni(OH)2 precipitate will be formed from a solution containing nickel ions
in a concentration of 0.01 mol/L (Ks=1.6х10-14)?
7. The mass concentration of molybdenum in a saturated solution of barium molybdate BaMoO 4 is 19.2
mg/L. Calculate the solubility constant of this salt.
8. Calculate the solubility (mol/L, g/L) of Ag2MoO4 silver molybdate in water, if the solubility
constant of this salt is 2.810-9.
9. Calculate the mass of magnesium carbonate in 750 ml of its saturated solution.. KS(MgCO3)=2.110-5.
10. Equal volumes of solutions of lead acetate and sodium oxalate were mixed. The concentrations of
both solutions were equal to 0.001 mol/L. Would a precipitate be formed? KS(PbC2O4)=4.810-10.
11. Name the following compounds and determine the degree of oxidation of the central atom: (а)
[CrCl(H2O)5]SO4; (b) [ZnCl2(NH3)2]
12. Write down the equations of primary and secondary dissociation and the expression for the complex
compound instability constant: K4[Mn(CN)6], [CrCl(H2O)5](NO3)2 , [СоF3(H2O)3].
13. Write the formulas of complex compounds and characterize their structure: (а) potassium
pentanitrobromoplatinat (IV); (b) hexaammine nickel (II) chloride.
Questions for self-study: Give examples of heterogeneous and metal-ligand equilibria occurring in the
human body. What factors influence these equilibria? How? Give examples of complex compounds of a
living organism.
Lesson №6
Physical chemistry of surface phenomena. Chromatography

- characterize and classify surface phenomena
- calculate the surface activity and adsorption of the solute at liquid and at solid surfaces
- explain the process of chromatographic separation of substances and the method of ion
exchange adsorption
- characterize the use of chromatographic methods for biomedical purposes
- characterize the adsorption of diphilic molecules at the interface of liquids with different
polarity and show the orientation of the molecules in the surface layer
Bibliography
Required reading:

1. Surface phenomena: adsorption, desorption, surface activity, adsorption equilibrium, chemisorption
2. Adsorption on a moving interface. Gibbs equation. The orientation of surfactant molecules in the
surface layer. Biological membrane structure.
3. What is the surface tension isotherm? What is an isotherm adsorption? Explain the differences between
positive and negative adsorption. Traube’s Rule.
4. Adsorption on the surface of a solid adsorbent. Selective adsorption. How does the ability to
adsorption depend on the charge of ions? Fajans' rule, (examples).
5. Formulate the main states of the theory of Langmuir. Langmuir adsorption equation and its analysis.
6. Give the Freundlich adsorption equation. How could the empirical constants in this equation be
calculated?
7. The main featureas of adsorption from solutions. Describe the ion-exchange adsorption and its areas of
application in medicine. Explain the essence of the process of water purification by ion exchange. Give
the equations of reactions occurring in ion-exchange chromatography.
8. What is chromatography? Classification of chromatographic methods of analysis according to the
method of implementation and the separation mechanism. Describe the use of chromatographic
methods in biomedical research and in sanitary and hygienic purposes.


1. What are the features of the surface layer? What processes can occur at the phase interphase?
2. Give examples of physical adsorption and chemisorption.
3. Give examples of surfactants.
4. Give examples of diphilic molecules, indicate their hydrophilic and hydrophobic parts. How does
surface activity in homologous series change?
5. Show schematically surface tension isotherms for solutions of propanol, hexanol and butanol of
same concentrations.
6. Ethanol is used as an antidote for methanol poisoning. Explain this use of ethanol.
7. There are 1M solutions: (a) sugar; (b) acetic acid; (c) sodium sulfate; (d) stearic acid. Place the
solutions in order of increasing surface tension. Explain this. Choose surfactants fron this group of
compounds.
8. Show schematically orientation of surfactant molecules in a saturated adsorption layer at the (a)
water-air and (b) benzene-water interface.
9. Give examples of polar and non-polar adsorbents. How does adsorption depend on the specific
surface of the adsorbent?
10. *Give examples illustrating the Rebinder's rule (of alignment of the polarities of the phases. Offer
an adsorbent to remove phenol from water. Explain your choice.
11. From the groups of ions listed below, select those that will be primarily adsorbed on the surface of
(a) silver chloride; (b) barium sulfate; (c) iron hydroxide. Cations: Al3+, Na+, Ca2+, Ag+, Ba2+, Fe3+,
Mg2+. Anions: SO42-, PO43-, Cl-, NO3-, OH-, CH3COO-. How will the precipitate surface be charged
in each case?
12. Compare the surface activity of propionic and butyric acids in aqueous solutions in this
concentration range:
С, mol/L σ, mN/mol
Propionic acid Butyric acid
0.0312 69.5 65.8
0.0625 67.7 60.4
Is the Traube’s Rule complied?
13. There are novocaine solutions with concentrations of 0.2 mol/L and 0.15 mol/L and cocaine
solutions with same concentrations. With a decrease in concentration, the surface tension of the
novocaine solution increased from 6.9∙10-2 N/m to 7.1∙10-2 N/m, and for a cocaine solution from
6.5∙10-2 N/m to 7.0∙10-2 N/m. Compare (a) the surface activity and (b) adsorption of these two
substances in a given concentration range at a temperature of 25°C.
14. *The adsorbtion capacity of adsorbent in respect to cholesterol is 0.7 μmol/g. Calculate the mass
of cholesterol adsorbed from blood plasma containing 4.8 μmol/ml cholesterol; K = 2 μmol/ml,
the molar mass of cholesterol is 386.6 g/mol? How will the adsorption change if the plasma
cholesterol concentration rises to 5.4 μmol/ml?
15. Calculate the amount of acetic acid, which is adsorbed by 100 g of soil. If the equilibrium
concentration of acetic acid in the solution is equal to15.5 mole/l, and Freundlich's equation
empirical constants are К=6.5 and 1/n = 0.12.
16. *Calculate graphically empirical constants К and n in Freundlich equation using the experimental
data obtained by carbon adsorption of valeric acid from aqueous solution at 25 °С:
c, mmole/sm3 0.006 0.025 0.053 0.118
Г, mmole/g 0.44 0.78 1.04 1.44

17. Explain the processes happened during the water purification by ion exchange chromatography.
Write equations of the reactions.
18. Explain how the separation of substances in the method of adsorption chromatography happens.
What is this method based on?
1. Using the Traube's rule, define how many times the surface activity of palmitic acid (С15Н31СООН) is
less than surface activity of eicosenic acid (С19Н39СООН).
2. What does the adsorption isotherm illustrate? Give example of adsorption isotherm scheme.
3. Schematically show on the same graph the isotherms of surface tension of the butanoic, propionic and
acetic acids. Compare the surface activity of acetic and propionic acid at the same temperature under the
condition of equality of their concentration.
4. How does the surface tension of water change if following substances will be added: a) propyl alcohol;
b) sodium chloride; c) soap?
5. How are diphilic molecules adsorbed at the water-oil interface? What determines their orientation?
6. What are the features of adsorption of strong electrolytes? What is selective adsorption rule?
7. Compare the surface activity of propionic and butyric acids in aqueous solutions in this concentration
range:
С, mol/L σ, mN/mol
Propionic acid Butyric acid
0.25 64.5 55.1
0.125 60.2 47.9
Is the Traube’s Rule complied?
8. Calculate the value of adsorption of water solution of caproic acid (С5Н11СООН) at 15оС, if its
concentration is 0.25 mole/l, surface tension of the solution is equal to 35∙10 -3 N/m, surface tension of
water is equal to 73.4∙10-3 N/m.
9. Determine the type of adsorption of sulfuric acid in water, if the concentration of sulfuric acid in water
is equal to 2.33 mole/l, surface tension of the solution is equal to 75.20∙10 -3 N/m, surface tension of water
is equal to 73.05∙10-3N/m, temperature is 18оС.
10. At a given temperature, 2.96∙10-3 mol/g of substance is adsorbed from a surfactant solution with a
concentration of 0.2 mol/L by some adsorbent. Calculate the adsorption capacity of the adsorbent Г∞ (in
mol/g) if the constant K value is 0.07 mol/L.
11. Calculate the acetic acid adsorption on a solid adsorbent, if the equilibrium concentration of acetic
acid is 0.22 mole/l, аndempirical constants К and n in Freundlich equation are equal to К=0.50 mole/g;
n=0.45.
Questions for self-study: Give examples and explain the use of the adsorption process and adsorbents in
medical practice. Explain how the adsorption of substances depends on the nature of the adsorbent.
Lesson №7
Physico-chemical properties and stability of disperse systems

- characterize and classify dispersed systems
- give a comparative description of the properties of true, colloidal and coarse systems
- record and explain the structure of the micelle of the colloidal solution (sol) obtained by
chemical condensation
- characterize methods of purification of colloidal solutions
- assume the structure and charge of the micelle, knowing the concentration and volume of the
reacting substances
- characterize the properties of colloidal solutions and their stability factors
- calculate the value of the coagulation threshold and the coagulating ability of the electrolyte
- characterize the structure of surfactant micelles in their solutions (colloidal surfactants)
Bibliography
Required reading:

1. Dispersed systems. Basic concepts. Methods of classification of dispersed systems.
2. Dispersion methods and condensation methods of colloidal systems obtaining. Peptization.
3. The structure of the micelle. EDL (electrical double layer), electro thermodynamic potential,
electrokinetic potential.
4. Properties of dispersed systems: molecular-kinetic, electrokinetic, optical properties. Electrophoresis.
Electroosmosis. Medical applications.
5. Methods for the purification of colloidal solutions: dialysis, electrodialysis, ultrafiltration. The use of
dialysis in medicine.
6. Thermodynamic stability, sedimentative and aggregative stability of colloidal solutions.
7. What factors cause coagulation of sols? Stages of coagulation. Colloidal protection. Role of
coagulation in the living organism. Coagulation threshold and electrolyte coagulating ability.
Additivity, synergism and antagonism of the action of a mixture of electrolytes.
8. Coarse-dispersed systems: aerosols, suspensions, emulsions. Properties and application in medicine.
Colloidal surfactants.
9. The formation of direct and inverse emulsions. Types of stabilizers.

Assessment: Summative, set on the basis of solving problems/cases (Practical skills 1,2,3,4)

1. Give examples of true, colloidal and coarse systems. Explain your choice.
2. Write a scheme of the micelle structure for sol:
a) Silver chloride, stabilized by sodium chloride
b) Lead (II) chloride, stabilized by potassium chloride
c) Iron (III) hydroxide , prepared by adsorption peptization; peptizing agent - iron (III) chloride
d) Iron (III) hydroxide , prepared by chemical peptization; peptizing agent – hydrochloric acid
e) Prussian blue, stabilized by iron (III) chloride
f) Prussian blue, stabilized by potassium hexacyanoferrate (II)
3. What are the features of the molecular kinetic and optical properties of colloidal dispersed
systems?
4. What phenomena are observed when a potential is applied to a colloidal solution? Explain.
5. In which direction do arsenic sulfide sol particles stabilized by hydrogen sulfide acid move by
electrophoresis (name electrode)? Write scheme of this sol micelle structure.
6. Explain the processes that occur during dialysis, electrodialase, vividialysis.
7. *Equal volumes of solutions were mixed: 1% calcium chloride and 1% sulfuric acid (take
densities equal to 1 g/mL). Write the micelle structure of the formed calcium sulfate sol. To which
electrode will particles of this sol move during electrophoresis?
8. What determines the stability of a colloidal solution? What happens when electrolyte is added to
sol?
9. Coagulation of 1.5 L of gold sulfide sol occurred after addition of 570 mL of a 0.2 M sodium
chloride solution. Calculate the coagulation threshold of a sol with sodium ions.
10. * 250 ml of a 0.0001 M silver nitrate solution was added to 100 ml of a 0.03% NaCl solution
(densities of both solutions are 1 g / ml) . Write the sol micelle structure. Which of the following
electrolytes will cause coagulation of this sol with the lowest threshold of coagulation: KCl,
Ba(NO3)2, K2CrO4, MgSO4, AlCl3?
11. *Thresholds for the coagulation of the unknown sol are equal to: 189 mmole/L for KCl; 183
mmole/L for K2SO4; 2.9 mmole/L for CaCl2. Determine the charge of the sol.
12. The coagulation threshold of the sol by 0.1M potassium dichromate solution is 0.063 mol/L.
Calculate the volume of this electrolyte, which must be added to 10 liters of aluminum hydroxide
sol to cause its coagulation.
13. Silver iodide sol was prepared by mixturing of equal volumes of two solutions: 0.04N KI and
0.01N AgNO3. Which of electrolytes would have highter threshold of coagulation – MgCO 3 or
K3[Fe(CN)6]? Why?
14. The coagulating ability of electrolytes with respect to a certain sol decreases in sequence: Na 3PO4
→ K2SO4 → NH4NO3. What is the charge of colloidal particles? Give examples of electrolytes
whose coagulating ability is approximately equal to the given compounds' one.
15. *A lead (II) bromide sol was obtained by mixing solutions of lead acetate and calcium bromide.
The coagulating ability of magnesium nitrate with respect to this sol is greater than the
coagulating ability of ammonium sulfate. Write the micelle formula of this sol.
16. *Give a scheme of the structure of emulsions of the following types: (a) oil/water and (b)
water/oil. Use hydrophilic and hydrophobic emulsifiers..
17. *Describe the micelle formation process in surfactant solutions. Write a scheme of surfactant
micelles formation in water. How does the micelle structure depend on the concentration of
surfactants in solution?
1. Compare molecular kinetic and optical properties of colloidal solutions with the properties of coarse
and true solutions. What is a Tyndall effect?
2. Write a scheme of the micelle structure for sol:
1) silver nitrate sol stabilized silver bromide;
2) iron (III) hydroxide sol obtained by hydrolysis reaction;
3) arium carbonate sol stabilized by barium chloride;
4) potassium sulfate sol stabilized barium sulfate.
3. Silver iodide sol obtained in excess AgNO3. To which electrode would move particles of the sol during
electrophoresis? Write the scheme of the micelle structure.
4. What volume of a solution of silver nitrate with a concentration of 0.001 mol/L should be added to 10
mL of a solution of sodium chloride with C(NaCl) = 0.002 mol/L to obtain a sol with positively charged
granules? Write a scheme of the sol micelles structure.
5. Which of the following substances cause peptization of freshly precipitated aluminum hydroxide: a)
potassium hexacyanoferrate (III); b) barium chloride; c) potassium hydroxide; g) aluminum chloride; d)
ammonia? Explain your answer.
6. In which order are coagulation thresholds for electrolytes CrCl 3, Ba(NO3)2, K2SO4 arranged if particles
of sol are negatively charged? Explain why.
7. To coagulate 10 ml of a sol of silver iodide with a negative charge of particles, 0.45 ml of a solution of
0.05 M barium nitrate solution is required. Find the coagulation threshold of of barium nitrate solution for
this sol..
8. Coagulation of 4 L of iron (III) hydroxide sol occurred after addition of 0.91 mL of a 10% magnesium
sulfate solution (density 1.1 g/mL). Calculate the sol coagulation threshold with sulfate ions.
Questions for self-study: Describe the use of the following processes in biomedical practice:
electrophoresis, dialysis (vividialysis).
Lesson №8
Redox reactions and equilibrium. Electrodes` potential. Midterm №1

- compare the oxidizing or reducing abilities of systems
- determine the probable direction of redox reactions
- explain the device and the calculation of the potential of the electrodes of the first and second
kind, redox electrodes
- calculate electrode potentials according to the Nernst equations
- calculate the EMF of electrochemical systems
- show the level of knowledge on topics of midterm control
- demonstrate a level of understanding of the essence and basic laws of processes occurring in
the body from the point of view of thermodynamics, kinetics, protolytic theory, etc.
- illustrate the assimilation of the basics of electrochemistry, basic concepts and surface
phenomena, and chromatographic analysis
- show knowledge on the classification, methods of obtaining, cleaning and physico-chemical
properties of disperse systems
- characterize the biological role of complex compounds, nutrients and the use of their
compounds in medicine
- explain the biomedical aspect of all the topics listed above
Bibliography
Required reading:

1. The potential at the interface of phases. Indicator electrodes and reference electrodes.
2. Calculation of potentials of electrodes of the first and second kind and redox electrodes. Nernst
equations.
3. Galvanic cells. Calculation of the electromotive force of the cell.
4. Biological importance of redox processes and redox potentials.
5. Spontaneity of redox processes. Equilibria in redox systems.
6. The use of potentiometric methods in biomedical research.
To prepare for midterm control:

Use questions given for each lesson on all topics covered.

Assessment: Midterm. Summative (written control, set on the basis of solving problems/cases)

1. What is the measure of the oxidizing and reducing ability of the substances? How could be
compared their redox ability?
2. Calculate the potential of the silver electrode placed in a solution of silver nitrate with a
concentration of 0.01 mol/L. What kind of electrode is it? (φоAg+/Ag = +0.80 V)
3. Calculate the potential of a hydrogen electrode placed in a solution of a strong monobasic acid
with a concentration of 0.002 mol/L.
4. In which conditions most of biochemical redox processes take place? The term "midpoint" of the
potential (normal electrode potential).
5. * What factors influence the redox properties of matter? Describe the effect of pH on the oxidative
properties of the permanganate ion.
6. *Methaemoglobin contains Fe3+, haemoglobin – Fe2+. Mass fraction of methaemoglobin (% from
total hemoglobin) changes with age: newborns have 6.22%, children of 1-3 months - 2.21% , in
children 1-3 years of 1.13% in children 7-14 years of 1.08%. How does the redox potential of the
system change if normal potential of the system methemoglobin / hemoglobin is equal to
φо’(Hb-Fe3+/ Hb-Fe2+) =0.17 V at temperatureТ=310 К?
7. Calculate ratio of concentrations of oxidized and reduced forms of biological redox systems
«cytochrome Fe3+ + ē ↔ cytochrome Fe2+» at temperature 298 К, if the redox potential of the
system is 0.058 V (φ0 = 0.04V).
8. * The cell consists of two electrodes: a hydrogen electrode in the gastric juice, and a saturated
calomel electrode. Calculate the concentration of hydrogen ions and the pH of gastric juice if
EMF of this element at 18°C is 0.330 V. The potential of saturated calomel electrode at this
temperature is 0.248 V.
9. * In which direction will the following processes proceed in an acidic medium in a standard state:
(а) Sn(IV) + Mn(II) ↔ Sn(II) + Mn(VII); (b) Cr(III) + Mn(VII) ↔ Cr(VI) + Mn(II); ( с) Sn(IV) +
Cr(III) ↔ Sn(II) + Cr(VI)? (φоSn4+/Sn2+ = +0.14 V; φоMn7+/Mn2+ = +1.53 V; φоCr6+/Cr3+ = +1.33 V)
10. *Calculate the potential of redox system СН3С(О)Н + 2H+ + 2ē → СН3СН2ОН in the conditions
of the human body if aldehyde concentration is equal to 10 -5 mole/l and alcohol concentration is
equal to 10-2 mole/l. Normal electrode potential for the system СН3С(О)Н, 2H+/СН3СН2ОН is
equal to 0.216 V.
1. Calculate the electrode potential of cadmium in the cadmium (II) nitrate solution, if activity of
cadmium ions is 0.02 mol / l (φоCd2+/Cd = -0.40 V).
2. How does the potential of a silver electrode change at a dilution of the silver nitrate solution is 10
times?
3. Calculate the potential of a hydrogen electrode placed in a solution with pH = 8.
4. Calculate the potential of a platinum electrode placed in a solution containing soluble salts of Sn (II)
and Sn (IV) at concentrations of 0.02 mol/L and 0.05 mol/L, respectively. φоSn4+/Sn2+ = +0.14 V.
5. The reactions occurring in a cell, the calculation of the EMF. On example of Daniell cell..
6. The glass and silver chloride electrodes as an indicator electrode and a reference electrode for
determination of pH in biological fluids.
7. Calculate the standard electromotive force of the cell formed by iron and nickel electrodes, if the
standard electrode potentials of the systems are respectively-0.44 Vи -0.23 V.
8. Are these reactions spontaneous or nonspontaneous:
9. а) Cu2+ + H2 → Cu + 2H+ ; b) 2Fe3+ + H2 → 2Fe2+ + 2H+, if standard potentials considered redox
systems are: φоCu2+/Cu=+0.337 V; φоFe3+/Fe2+=+0.771 V; φо2H+/H2=0.000 V. Prove your answer with
calculation.
Questions for self-study: Describe the use of ion-selective electrodes in biomedical research.
Lesson 9
Bases of the structure and reactivity of organic compounds.
Reactivity of alcohols, phenols, thiols, amines

- describe the shape of an organic molecule based on its structure;
- apply IUPAC nomenclature rules;
- explain the mutual influence of atoms and guess the properties of organic compounds;
- determine the reaction center in the molecule and evaluate the reactivity of organic compounds;
- characterize the influence of the acid-base center, the nature of the radical on the strength of acids and
bases of organic compounds;
- write chemical reactions for functional groups of alcohols, amines, thiols, phenols.
Bibliography
Required reading:

1. Classification and nomenclature of organic compounds. Hydrocarbon radicals. Structural isomerism.
The concept of stereoisomerism of organic compounds: conformation and configuration. The
relationship of the spatial structure with their biological activity.
2. Conjugate systems with an open circuit, their types (π,π- conjugation, p,π- conjugation). Cyclic
conjugated systems. Aromaticity. Hückel's rule.
3. The mutual influence of atoms in the molecules of organic compounds. The concept of electronegativity of
atoms, polarizability of bonds. The concept of inductive and mesomeric effects, their role in the formation of
reaction centers in organic molecules.
4. The concept of the mechanism of organic reactions. Homolytic and heterolytic covalent bonds fission
(breaking). Types of reagents: radical, nucleophilic and electrophilic.
5. Classification of organic reactions according to the result of the reaction. Substitution reactions (S), additions
(A), elimination (E), isomerization (rearrangement), redox reactions, hydrolysis.
6. Acid-base properties of alcohols, phenols, thiols and amines. The effect of the acid-base center and
radical on the strength of acids and bases.
The role of redox reactions in biochemical processes. Oxidation reactions of:
1) primary and secondary alcohols;
2) hydroquinone;
3) thiol (a) oxidation to disulfide (mild thiol oxidation); (b) strong oxidation.
Test reactions:
1) of polyhydric alcohols (Cu(OH)2 without heating);
2) of phenols (FeCl3);
3) deamination of primary amines (with НNO2);
Alkylation and acylation reactions of (a) amines; (b) thiols. Acylating agents. Coenzyme A as a
acylation coenzyme of biochemical reactions.
The role of hydrogen bonds in the formation of three-dimensional structure of proteins,
polysaccharides, nucleic acids. Show hydrogen bonds formation in alcohols, phenols, amines.

1. Add hydrogen atoms and name compounds according to IUPAC System.
Formula Systematic name
C
C-C-C-C
C C
C-C=C-C
C C
C=C-C=C-C
C
C-C
C
2. Determine the class of organic compounds and name them according to IUPAC System.
Formula Class of compound Systematic name
3. Write the structural formulas of the following compounds.

Systematic name Formula
dimethylamine
butanone
1,2,3-propantriol
2-methyl-2-propanol
2-hydroxybenzoic acid
2-amino-3-methylbutanoic acid
4. Write and name the radicals of: (a) methane; (b) ethane; (c) propane (2 radicals); (d) butane (4
radicals); (e) benzene and toluene (4 radicals).
5. Identify primary (1o), secondary (2o), tertiary (3o), and quaternary (4o) carbon atoms in the
compound .
6. For each of the following pairs of structural formulas, indicate whether the pair represents (1) the
same compound or (2) different compounds that are constitutional isomers or (3) different
compounds that are not isomers or (4) stereoisomers
1) and
2) and
3) and
4) and
7. Draw the possible structures of alkene C5H10 isomers which may present in cis- and trans- forms.
8. * Show graphically the electronic effects in the following compounds: (a) propene; (b) acrylic acid
(propenoic acid).
9. Write the structural formulas of benzene and phenanthrene. Why these compounds may be referred
as aromatic compounds?.
10. * Show graphically the distribution of electron density in: 1) toluene; 2) benzaldehyde..
11. Prove the acidic nature of ethanol, phenol, ethanethiol. Which of these compounds could react with
sodium hydroxide? Write the reactions.
12. How does the nature of the radical affect the basicity of the following amines: methylamine,
methylethylamine, aniline. Write the salt formation reaction of these compounds with hydrogen
chloride.
13. Write the oxidation reactions of the following compounds: 1) ethanol; 2) propanol-2; 3)
hydroquinone; 4) methanethiol. Which of these reactions underlies the action of coenzyme Q?
14. Write the formation reactions: (1) an ether with two ethanol molecules; (2) an ester of acetic acid
and ethyl alcohol; (3) copper glycerate, the reaction of glycerol with Cu(OH) 2 without heating.
What are products of the reactions?
15. Write the reactions of ethylamine with: 1) methyl iodide; 2) acetyl chloride; 3) НNO2, deamination
reaction. What are products of the reactions?
Class format:
Explanation, implementation and discussion of situational tasks, exercises, work in small groups.
1. Add hydrogen atoms and name compounds according to IUPAC System.
Formula Systematic name
C-C-C-C-C
C-C-C
C-C
C-C-C-C-C
C
C=C-C
C-C-C-C
C-C
C-C
C
C
2. What classes of organic compounds (a) adrenaline (the hormone of the adrenal medulla) and (b)
vitamin E belong to?
ÍÎ ÑÍ ÑÍ 2
NH ÑÍ 3
ÍÎ ÎÍ
Àäðåí àëè í
(a)
(b)
3. Identify primary (1o), secondary (2o), tertiary (3o), and quaternary (4o) carbon atoms in the compound
4. Write the structural formulas of the given radicals

1) propyl
2) isopropyl
3) sec-butyl
4) tert-butyl
5) phenyl
6) vinyl
7) p-tolyl
5. For each of the following pairs of structural formulas, indicate whether the pair represents (1) the same
compound or (2) different compounds that are constitutional isomers or (3) different compounds that are
not isomers or (4) stereoisomers
а) and
b) and
c) and
6. Name these compounds according to IUPAC System
а)
b)
c)
d)
7. Using the IUPAC names write structural formulas of the compounds below
Systematic name Formula
1)propenoic acid
2)2-methyl-2 butanol
3) 1,2-Ethandiol
4) 2-amino-3-mercaptopropanoic acid
8. Complete the following reactions and name the products of the reactions
1) С2Н5 ОН + Na
2) CH3CH2 SH + NaOH
3) С6Н5 NH2 + HCl
4) CH3 ОН
5) CH3CH2 S-S CH2CH3
6) CH3СН2 ОН + СН3 ОН
7) CH3 ОН + Н3PO4
8) НО СН2СН2 ОН + Сu(OH)2
9) CH3NH2 + HNO2
10) CH3 NH2 + CH3 I
11) CH3СН2 NH2 + (CH3СО)2О
*9. Identify B and C products in the following scheme. Write the reactions
Questions for self-study:

Describe the relationship of the spatial structure of organic compounds with their biological activity. Give
examples.
Lesson 10
Reactivity of aldehydes, ketones, carboxylic acids.
Amino alcohols, aminophenols, phenolic acids, hydroxy, oxo acids.

- write chemical reactions for functional groups of aldehydes, ketones, carboxylic acids;
- determine the center of chirality in a molecule and depict stereoisomers of the molecule;
- write the formulas of the most important heterofunctional compounds;
- characterize the chemical properties of heterofunctional compounds by writing chemical reactions for
the studied functional groups;
- write test reaction for different functional groups of organic compounds.
Bibliography
Required reading:

1. The structure of carbonyl and carboxyl groups. The effect of radical substituents the reactivity of
carbonyl compounds and the strength of acids.
2. Reactions of nucleophilic addition (АN) of aldehydes and ketones:
1) reduction reactions (with metal hydrides);
2) reaction with water;
3) reaction with alcohols.
3. Reactions of aldol addition (aldol condensation). The biological significance of this reaction.
4. Test reactions to the aldehyde group - oxidation of aldehydes when heated:
1) ammonia solution of silver hydroxide [Ag(NH3)2]OH (Tollen's reagent, “silver mirror reaction”);
2) copper hydroxide (II) (Trommer reaction);
3) with Fehling's reagent.
5. Reactions of nucleophilic substitution (SN) of carboxylic acids. Formation of the following
compounds:
1) esters (esterification reaction) and thioester.
2) amides;
3) anhydrides;
Counter reaction - hydrolysis reactions. The biological role of hydrolysis reactions.
Describe acyl phosphates and acetyl coenzyme A as natural macroergic acylation reagents and
characterize their biological role. Phosphorylation reactions.
6. Properties of dicarboxylic acids: decarboxylation and the cyclic anhydrides formation.
Decarboxylation as a pathway for the biogenic amines and bioregulators formation.
7. Intermolecular hydrogen bonds of carboxylic acids.
8. Heterofunctional compounds, as compounds involved and formed in the metabolism. The biological
significance of both metabolites and intermediates. Catabolism and Anabolism.
9. Optical isomerism. Asymmetric carbon atom. Optical activity. The configuration standard is glycerin
aldehyde. Stereoisomers with one and several centers of chirality. D and L rows. Enantiomers.
Diastereomers. Racemate.
10. Amino alcohols: ethanolamine, choline, acetylcholine, their biological significance as
neurotransmitters.
11. Aminophenols. Dopamine, norepinephrine, adrenaline are biogenic amines, their biological
significance as hormones.
12. Hydroxyacids: glycolic, lactic, malic, tartaric and citric acids.
13. Aldehyde and keto acids (oxo acids): glyoxylic, pyruvic, acetoacetic, oxaloacetic, α-ketoglutaric acid.
Keto-enol tautomerism on the example of acetoacetic ester.
14. Phenolic acids: salicylic, acetylsalicylic, para-aminosalicylic acid - as medicines.

1. Compare strength of acids and arrange the following acids in order of increasing acidity: acetic,
formic, propionic, oxalic, citric acids. Explain your answer..
2. Write the following reactions: (1) acetic aldehyde reduction; (2) acetone reduction; (3) ethanal
oxidation by copper (II) hydroxide without heating.
3. Which compound forms more stable compound with water — ethanal or trichloroethanal?
Write reactions.
4. Write the reaction of acetic aldehyde with ethyl alcohol. Note hydrolysis of hemiacetals and acetals.
5. Write the condensation reaction of acetic aldehyde with propionic aldehyde.
6. *What compounds can form during the reactions of acrylic aldehyde (propenal): (1) oxidation; (2)
reduction? What test reactions could be used to prove the presence of: (a) a double bond in propenal;
(b) an aldehyde group in propenal; (c) hydroxyl groups in the product of its oxidation? Write
reactions.
7. Write reactions: 1) ethyl ester of malonic acid formation; 2) acetic acid + НSКоА.
8. Write the reaction of the following anhydrides formation: 1) acetic anhydride; 2) mixed anhydride
acetyl phosphate.
9. Write the reaction of acetic acid amide formation with methylamine.
10. Why oxalic and malonic acids undergo decarboxylation when heated, whereas succinic acid forms an
anhydride. Write reactions.
11. Write:
1) acidic hydrolysis of ethyl acetate
;
2) alkaline hydrolysis of N-ethylacetamide
What are the products of hydrolysis?

12. Write down the structural and optical isomers of hydroxybutanoic acid. Name them according to the
IUPAC nomenclature.
13. *For the following compounds:
1) 2) 3)
write reactions (1) with sodium hydroxide; (2) with hydrochloric acid.
Which functional groups will form salts with sodium hydroxide? Which of these acids can be detected
by reaction with copper (II) hydroxide without heating? Write these reactions.
Which of the compounds can react with a solution of iron (III) chloride?
14. * Write the reactions according to the following scheme: ethanolamine  choline  acetylcholine.
Name the type of these reactions.
15. Adrenaline is the hormone of the adrenal medulla, whereas norepinephrine(noradrenaline) and
dopamine are the precursors of adrenaline:
ÍÎ ÑÍ ÑÍ NH 2 Í Î ÍÎ ÑÍ ÑÍ NH ÑÍ
2 2 ÑÍ ÑÍ 2
NH 2 2 3
ÍÎ Î Í ÎÍ
ÍÎ ÍÎ
Äî ô àì èí Í î ðàäðåí àëè í Àäðåí àëèí
Сlassify these compounds according to their functional groups. Characterize their acid-base
properties. What reaction could be used to get adrenaline from norepinephrine. Write the scheme of
this reaction.
16. Write the reactions: 1) oxidation of lactic acid with NAD +; 2) recovery of oxaloacetic acid with
NADH2. What are the reaction products obtained?.
17. Which of carboxylic groups of 2-oxopentanedioic (α-ketoglutaric) acid could be easier
decarboxylated and why? Write this reaction and name the reaction product.
18. Write the keto-enol tautomerism equilibrium of ethyl acetoacetic acid (3-oxobutanoic acid). Which of
the tautomeric forms of acetoacetic acid could react with bromine water? Write the reaction.
19. *Write aldol condensation reaction of oxaloacetic (oxobutanedioic) acid with acetyl coenzyme A.
20. *Write the reactions of the following transformations: fumaric acid (butendioic acid) → malic acid
(hydroxybutanedioic acid) → oxaloacetic acid (oxobutanedioic acid)
X. What reagents should be used for these reactions?
21. Write the reactions of salicylic acid derivatives formation: (a) methyl salicylate; (b) sodium salicylate;
(c) phenyl salicylate; (d) acetylsalicylic acid. What reagents should be used for these reactions?
Class format:
Explanation, implementation and discussion of situational tasks, exercises, work in small groups. The
numbers of mastered practical skills are №1,2,3.
Assessment:
Written control of tickets is carried out (solution of situational problems), a summative assessment of a
practical lesson is set.
1. Name the following compounds according to the IUPAC nomenclature
Formula Common names IUPAC names
* Rational nomenclature
Hydroxy acids
glycolic acid (involved in glycolysis)
lactic acid
(L (+) -isomer is found in muscle)
malic acid
(involved in the Krebs cycle)
tartaric acid
(has antioxidant properties)
citric acid (involved in the Krebs cycle)
Oxo acids
glyoxalic (glyoxylic) acid
pyruvic acid
(the main in the Krebs cycle)
acetoacetic acid
(refers to "ketone bodies" and is
accumulated in the body in diabetic
patients (as well as acetone is))
oxalacetic acid
* α-ketoglutaric acid
Amino alcohols
colamine
(part of phospholipid membranes)
choline
(part of phospholipid membranes, choline
ester is a neurotransmitter)
Phenolcarboxylic acid
salicylic acid
(forms aspirin with acetic acid)
para-aminosalicylic acid
(anti-tuberculosis action)
2. Compare the strength of the following acids and arrange them in order of increasing acidity:
trichloroacetic, acetic, formic, monochloroacetic acids. Explain your answer.
3. Complete the following reactions and name the products of the reactions
12) CH3C(O)CH3
13) Н2С=О + Н2О
14) CH3СН2CH=О + 2СН3 ОН
15) Н2С=О + CH3CH=О
16) Н2С=О + [Ag(NH3)2]OH
17)
18)
19) CH3SH + CH3COOH
20) CH3COOH + NH3
21) CH3COOH + CH3COOH
22) НООС СН2 СООН
4. Write down the structural and optical isomers of hydroxypropanoic acid. Name them according to the
IUPAC systematic nomenclature.
5. Complete the reactions and name the products:
1)
2)
3)
4)
5)
*6. Identify A and B products in the following scheme. Write the reactions
А Б
2) butendioic acid А Б

Explain the biological role of acylation, hydrolysis, and condensation reactions. Give examples.
Lesson 11
Amino acids. Biologically important properties of α-amino acids. Peptides.
The structure and properties of protein molecules. Biopolymer solutions.

- write chemical reactions characterized properties of amino acids as heterofunctional compounds;
- describe test reactions used for recognition and identification of amino acids and protein molecules;
- characterize the properties of biopolymer solutions;
- describe the main processes resulting in decrease of protein solutions stability;
- explain the principles of the electrophoretic method using for determination of isoelectric point of a
protein and of separation of a proteins mixture.
Bibliography
Required reading:

1. Classification of α-amino acids:
a) polar (ionogenic and non ionogenic) and nonpolar;
b) acidic, basic and neutral;
c) essential and non essential.
2. The structure and nomenclature of 20 α-amino acids of a living organism.
3. Acid-base (amphoteric) properties of α-amino acids. The zwitterion (bipolar ion) formation.
4. Chemical properties of amino acids as heterofunctional compounds:
Reactions of -СООН groups:
а) write amide formation reaction for (i) aspartic acid, (ii) glutamic acid.
b) write decarboxylation reaction for (i) tryptophan; (ii) histidine; the of biogenic amines and
bioregulators formation.
Reactions of -SH groups:
а) write reaction of cysteine mild (weak) oxidation. Biological importance of the reaction.
b) write reaction of cysteine strong oxidation which followed by decarboxylation.
Reactions of -NH2 groups:
а) deamination reactions: oxidative; non-oxidative; hydroxylation;
b) alkylation;
c) acylation.
Reactions of -ОН groups:
а) write oxidation reactions for (i) serine; (ii) threonine;
b) esterification reaction of alpha amino acids with organic and inorganic acids.
5. Peptides formation. Nomenclature. Electronic and steric structure of the peptide group. Acidic and
alkaline hydrolysis of peptides.
6. Tripeptide glutathione γ-Glu-Cys-Gly. Its biological significance.
7. Types of interaction between side chains of amino acids: hydrophobic, ionic, hydrogen and disulfide
bonds formation.
8. Test reactions of alpha amino acids: xanthoproteic reaction, ninhydrin test, biuret test.
9. Biopolymers of a living organism. The biological role of proteins in the human body. Proteins as
polyampholytes. Isoelectric point of protein and methods for its determination. At what pH does the
protein behave as a base or as an acid? Electrophoresis as a method of proteins and peptides
separation. How the charge of a protein molecule could be determined?
10. Swelling. Limited and unlimited swelling. The degree of swelling. How swelling depends on various
factors?
11. Stability of polymers' solutions. Factors that violate the stability of solutions of biopolymers:
denaturation, thixotropy, syneresis, salting out, coacervation. Medical and biological significance of
these processes.
12. Denaturation of proteins. Physical and chemical factors causing denaturation; the significance of the
process of denaturation for physiology.
13. Oncotic pressure of blood and its biological significance. Osmotic pressure of biopolymers solutions.
14. Viscosity of polymers' solutions. Viscosity of blood and other biological fluids. Concept of
biorheology.

1. Write the following reaction for (a) alanine and (b) aspartic acid: 1) zwitterion formation; 2) salt
formation with NaOH; 3) salt formation with HCl. Note the acid-base nature of these amino acids.
2. Write the deamination reactions of aspartic acid: 1) hydrolytic deamination; 2) non-oxidative
deamination; 3) oxidative deamination; 4) laboratory deamination with nitrous acid.
3. Write the following reactions for glutamic acid: (a) amide formation; (b) N-acyl derivatives
formation; (c) deamination with nitrous acid.
4. Write the following reactions: (1) histidine decarboxylation; (2) threonine esterification with
phosphoric acid; 3) threonine oxidation; 4) mild (weak) and strong oxidation of cysteine followed by
decarboxylation of the product of strong oxidation.
5. Write reactions of the following tripeptides formation: 1) Cis-Val-Asp; 2) Gly-Pro-Liz. Write their
full name. What could be said about value of isoelectric point of these tripeptides?
6. Write the structure of the brain neuropeptide Leu-enkephalin which has amino acid sequence Tyr-
Gly-Gly-Phe-Leu. What products are formed as a result of complete hydrolysis of this peptide in
presence of hydrochloric acid?
7. Write tripeptide glutathione formation reaction (-Glu-Cys-Gly). Characterize its biological
significance.
8. What type of bond could be formed between side chains of the following alpha amino acids: (a)
lysine and aspartic acid; (b) phenylalanine and valine; (c) tyrosine and aspartic acid? Show it
schematically
9. In what form does methionine (2-amino-4-methylthiobutanoic acid) predominantly exist: (a) as a
bipolar ion; (b) in solution with pH = 3? The isoelectric point of methionine is 5.8. Write the
appropriate structures
10. * It is recommended to rinse your mouth with a weak solution of sodium bicarbonate (pH ~ 8) after
taking glutamic acid in powder form. Why it is? It is known that isoelectric point of glutamic acid is
3.2?
11. * For the treatment of certain eye diseases, electrophoresis with a 2% cysteine aqueous solution is
carried out. Set to which electrode will molecules of this α-amino acid move: to positive (anode) or
negative (cathode)?
12. Two rubber samples of 5 g each were plased in benzene and toluene. After swelling mass of them was
11 g and 15.7 g respectively. In which of these solvents is the degree of swelling of rubber higher?
Calculate.
13. Isoelectric point of β-lactoglobulin is pI = 5.2. Determine the direction of movement of during
electrophoresis in a buffer solution with pH = 8.6 (to cathode or to anode). Explain the answer.
14. *Muscles' myosin is placed in a solution in which the concentration of hydrogen ions is 100 times
greater than in pure water. Determine the charge of protein molecules in this solution. Isoelectric point
of miosin is aproximately pH 5.1 to 5.3.
15. *Toward which electrode will β-lactoglobulin move in electrophoresis in a buffer solution containing
equal concentrations of hydrophosphate and dihydrophosphate anions (K a=6.3 x 10-8), if it remains at
the start at pH = 5.2?
Class format:
Assessment:
Formative (in the form of feedback; can be improved)
1. You are given IUPAC names of α-amino acids. Draw their structural formulas and write common
name of each of them
IUPAC name of α-amino acid Structural formula/common name
aminoethanoic acid
2-amino-3-hydroxypropanoic acid
2-amino-3-methylpentanoic acid
2-amino-4-methylthiobutanoic acid
2-aminopentanedioic acid
2,6-diaminohexanoic acid
2-amino-3-phenylpropanoic acid
2-amino-3-imidazolyl propanoic acid
pyrrolidine-2-carboxylic acid
2. Complete the following reactions. Name the products received
1) glycine + HCl →
2) valine + NaOH →
3) isoleucine
4) alanine
5) glutamic acid
6) glycine
7) aspartic acid + NH3 →
8) tryptophan
9) cysteine
3. Write reactions of the following tripeptides formation: 1) Lys-Pro-Met; 2) Try-Phe-Glu. Write their
full name. What could be said about value of isoelectric point of these tripeptides?
4. What type of bond could be formed between side chains of the following alpha amino acids: (a)
isoleucine and alanine; (b) two cysteine molecules; (c) glutamic acid and serine? Show it
schematically
5. In what form does leucine (2-amino-4-methylpentanoic acid) predominantly exist: (a) as a bipolar ion;
(b) in solution with pH = 8? The isoelectric point of methionine is 6.0. Write the appropriate
structures.
6. There are two enzymes with isoelectric point of 4.8 and 7.9 in solution. At what pH values could these
enzymes be separated? Explain the answer.
7. *At pH 6, insulin remains at the start during electrophoresis. To which electrode will insulin move in
a solution of hydrochloric acid with a concentration of 0.1 mol / L?
8. * Write the reactions according to the following scheme:
А B oxaloacetic acid C
9. What are the compounds A, B and C of the scheme?

Describe the role of proteins in the human body. Isoelectric point of proteins and methods for its
determination. Electrophoresis as a method of separation of proteins and peptides.
Lesson 12
Carbohydrates. Monosaccharides. Disaccharides. Polysaccharides

- find the center of chirality in the monosaccharide molecule and write its stereoisomers;
- write the formulas of the most important monosaccharides and characterize their reactivity;
- use test reactions to carbohydrates to detect monosaccharides in biological fluids;
- characterize the dependence of biological activity of carbohydrates on the structure and physical and
chemical properties.
Bibliography
Required reading:

1. Carbohydrates, classification, biological significance. Classification of monosaccharides according
the nature of functional groups (aldoses, ketoses) and the number of carbon atoms (pentoses,
hexoses).
2. Stereoisomerism of carbohydrates. Enantiomers Diastereomers Epimeres. α,β-anomers. Racemate.
3. Glucose, galactose, mannose, fructose, ribose, deoxyribose, xylose. Cyclooxothautomery. - and -
anomers. Fischer and Haworth projections. Glycoside hydroxyl. Mutarotation.
4. Formation and properties of - and - glycosides.
5. Oxidation of monosaccharides into -onic acids, -aric acids, -uronic acids. Decarboxylation of uronic
acids.
6. Reduction of monosaccharides: mannitol, sorbitol, dulcite, xylitol formation.
7. Test reactions based on oxidation reactions: silver mirror reaction (with Tollens reagent), reaction
with copper (II) hydroxide (Trommer reaction) and with Fehling reagent.
8. Reactions due to hydroxyl groups: (a) copper saccharate formation with copper (II) hydroxide; (b)
esters formation of monosaccharides with organic and inorganic acids (H2SO4, H3PO4).
9. Amino Sugars: glucosamine, galactosamine. Formation of O-acyl and N-acyl derivatives.
10. Reducing disaccharides (maltose, lactose): composition, type of bond.
11. Non-reducing disaccharide (sucrose): composition, type of bond.
12. Starch. Composition and structure of starch. Starch dextrinization. Test reaction. The structure of
amylose and amylopectin. The main types of bonds in these compounds.
13. Glycogen. Glycogen structural unit, types of bonds.
14. Connective tissue polysaccharides. Scheme of formation of disaccharide fragment of hyaluronic acid.
What are functions of hyaluronic acid in the body?
15. Scheme of disaccharide fragment formation of chondroitin-4-sulfate and chondroitin-6-sulfate. The
biological role of chondroitin sulfates.
16. Scheme of heparin disaccharide fragment formation. The biological role of heparin. Types of bonds
within disaccharide fragments and between them.

1. Write formulae of D- and L-glucose. What is the sign of belonging to the D-and L-series? Show the
asymmetric carbon atoms of glucose with asterisks. How could the total number of stereoisomers be
calculated?
2. Write the scheme of the cyclo oxo tautomerism of D-glucose and D-fructose. Write Fischer and
Haworth formulas of the cyclic isomers.
3. Write the reaction of -glucopyranose with methyl alcohol in the presence of HCl. What is the
difference between the obtained compound and ether?
4. Draw the scheme of oxidation reaction of glucose into: (a) gluconic acid; (b) glucaric acid.
5. Write the scheme of galactose oxidation to galacturonic acid, followed by decarboxylation. Write
galacturonic acid in both forms: open form and cyclic form.
6. Write the reactions of hydrogenation of glucose and fructose.
7. Write schemes of the following test reactions for glucose: (a) the "silver mirror" reaction; (b) reaction
with copper (II) hydroxide (when heated); (c) reaction with copper (II) hydroxide without heating.
8. Write scheme of formation reaction of 1,6-diphosphate-β, D-fructofuranose.
9. Write schemes of formation reactions of N-acyl and O-acyl derivatives of galactosamine: (a) with
acetic anhydride; (b) with sulfuric acid.
10. The β-D-galactose was treated with methyl alcohol in the presence of HCl, then product was oxidized
with diluted nitric acid, the resulting product was subjected to hydrolysis in an acidic medium, and
then decarboxylation reaction was provided. Write the appropriate reactions and name the products
received.
11. Write the reaction of formation of lactose, maltose and sucrose. Name the type of glycosidic bond in
these compounds. Which of these compounds are reducing disaccharides?
12. What are the similarities and differences between sucrose, maltose, lactose in the following reactions:
(a) with Felling reagent; (b) with copper (II) hydroxide without heating; (c) glycosides formation with
ethanol in the presence of anhydrous HCl; (d) hydrolysis reaction? Why does sucrose not react in a
"silver mirror" reaction?
13. Which reactions could be used for the following transformations?
maltose → glucose → gluconic acid
Write the reactions.
14. Write the following reactions: (a) sucrose → octaacetyl sucrose; (b) maltose → ethyl maltoside. What
reagents are used in these reactions?
15. Draw fragment of amylose and amylopectin.
16. Write the disaccharide fragment of chondroitin-6-sulfate (β, D-glucuronic acid and 2-deoxy-N-acetyl-
β, D-galactosamine-6-sulfate which are connected by β (13) glycosidic bond). Biological role.
17. Write a disaccharide fragment of hyaluronic acid (β, D-glucuronic acid and2-deoxy-N-acetyl-β, D-
glucosamine which are connected by β (13) glycosidic bond). Biological role.
18. Write scheme of formation of disaccharide fragments of heparin. What are the functions of heparin in
the body?
Class format:
numbers of mastered practical skills are №1,2,3,4.
Assessment:
1. Write structure of: (a) epimer of D-glucose; (b) diastereomer of D-glucose; (c) structural isomer of D-
glucose?.
2. Write the scheme of the cyclo oxo tautomerism of D-mannose and D-ribose. Write Fischer and
Haworth formulas for the cyclic isomers. Name α,β-anomers.
3. Complete the following reactions:
1) D-glucose D-glucuronic acid
2) - D-glucofuranose + C2H5OH
3) D-glucose D-glucaric acid
4) D-glucose D-gluconic acid
5) D-galactose
6) - D-glucofuranose + Н3РО4 →
7) D-galactose
8) D-galactose
9) -Д-глюкозамин
10) - D-glucopyranose + - D-glucopyranose →
11) sucrose
12) maltose
13) lactose + CH3OH
Name the products of the reactions.
4. Write the following reactions: a) glucose → penta acetyl glucose; b) ribose → tetramethyl ribose.
What reagents are used for these reactions?
5. Write the reactions according to the scheme:
sucrose → glucose → gluconic acid
6. Write the structural formula of the disaccharide formed by β-D-galactopyranose and α-D-
glucopyranose, which are linked by a β-1,4-glycosidic bond. Name this disaccharide. Write the
structural formula of the product of the interaction of this disaccharide with Cu(OH) 2 without heating.
Could this disaccharide react with Cu(OH)2 when heated? Write the reactions.
7. Write the disaccharide fragment of chondroitin-4-sulfate (β, D-glucuronic acid and 2-deoxy-N-acetyl-
β,D-galactosamine-4-sulfate which are connected by β (13) glycosidic bond).
8. Write the disaccharide fragment of heparin (N-sulfo-α,D-glucosamine-6-sulfate and β,D-glucuronic
acid which are connected by an α (14) glycosidic bond. Biological role.

Describe the biomedical value of carbohydrates.
Lesson 13
Saponifiable and unsaponifiable lipids

- characterize the properties of higher acids of lipids;
- know general structure of triacylglycerols and phosphoglycerides;
- describe the properties and hydrolysis reactions of saponified lipids;
- characterize the structure of unsaponifiable lipids;
- explain the biological significance of oxidative processes of fatty acids, lipids.
Bibliography
Required reading:

1. Classification and biological role of lipids.
2. The main fatty acids of the natural lipids, their structure. Cis-, trans-isomerism of unsaturated fatty
acids. Test reactions of unsaturated fatty acids (bromination, oxidation with an aqueous solution of
potassium permanganate).
3. Essential higher fatty acids as vitamins of "F" group. Biological role of omega-3, omega-6
polyunsaturated fatty acids.
4. Triacylglycerols, their structure, biological role and nomenclature. Triacylglycerols in nature.
5. Simple and mixed fats. Soft and liquid fats. The effect of degree of unsaturation of fatty acids on the
properties of fats. Iodine number as a measure of fat unsaturation.
6. Chemical properties of triacylglycerols: acidic hydrolysis, saponification, hydrogenation.
7. The concept of lipid peroxidation; β-oxidation of saturated fatty acids.
8. Phospholipids, their classification and biological role. Amino alcohols of phosphoglycerides; scheme
of conversion serine → ethanolamine → choline.
9. The general structure of phosphoglycerides. Phosphatidic acid. Phosphatidylserine,
phosphatidylethanolamine, phosphatidylcholine. Structure. The biphility of these compounds.
Hydrolysis.
10. Steroids classification. The general structure of steroids, order of numbering of carbon atoms.
11. Sterols: cholesterol, ergosterol. Sterols in nature. Biological role. Cholesterid, ergosterid. Vitamins D 2
and D3. Structure, biological importance.
12. Bile acids. Cholic acid. Deoxycholic acid. Structure. Paired bile acids. Glycocholic, taurocholic acids.
1. Draw cis and trans isomers of oleic acid. What is the configuration of natural unsaturated fatty acids?
2. What determines the consistency of fat? What do the following data mean: iodine value of human fat -
64, sunflower oil - 130?
3. Write reactions of the following fats formation: 1) 1-oleo-2,3-dipalmitin; 2) 1,2-dilinoleno-3-stearin.
What is the consistency of these fats? Which of them is fat and which is oil? Which of the fats has
higher iodine number?
4. What reactions can be used to distinguish triolein from tripalmitin? Give the reaction schemes.
5. Write the scheme of hydrogenation reaction of 1-linolenoyl-2-linoleoyl-3-oleolylglycerol. What is the
consistency of the initial fat and final product?
6. Write the reaction of tristearin hydrolysis: 1) with water in an acidic medium; 2) with sodium
hydroxide. Name the products of the reactions.
7. Write schemes of the following reactions: serine → ethanolamine → choline. What is the type of each
reaction?
8. Write D and L stereoisomers of glycero-3-phosphate. Which of them takes part in the
phosphoglycerides formation?
9. Write a scheme of lecithin (phosphatidylcholine) formation from glycero-3-phosphate with stearic and
linoleic acids. Show the polar and non-polar parts of the molecules.
10. Write the structural formula of 1-stearoyl-2-linoleoyl phosphatidylserine. Show ester bonds in the
molecule.
11. Write scheme of complete hydrolysis of 1-palmitoyl-2-oleoyl phosphatidylethanolamine in acidic
medium. What are the reaction products?
12. What sterol is a source of vitamin D3? Write the scheme of the reaction.
13. What vitamin is produced when ergosterol is irradiated with UV light? Write the scheme of this
reaction.
14. Write scheme of cholesteride formation and ergosteroide formation reactions with oleic acid.
15. Write the reaction of glycocholic acid and taurocholic acid formation. Characterize their biological
significance.
Class format:
Assessment:
Formative (in the form of feedback; can be improved).
1. Which of the following statements are true in relation to oleic acid?
1) there are two π bonds in the hydrocarbon radical
2) it is a part of natural lipids in the cis configuration
3) it is in a solid state at room temperature
4) its hydrocarbon radical contains 18 carbon atoms
5) it has an even number of carbon atoms
6) it is essential carboxylic acids
2. Write the formation reaction of: (a) 1,2-dilinoeloyl-3-palmitoylglycerol; (b) 1,2,3-trioleoidglycerol.
Do these fats have soft or liquid consistency? Which of the discussed triacylglycerols belongs to fats,
and which to oils? Which fat has the largest iodine number?
3. What reactions could be used to distinguish triolein from tristearin? What of them could be oxidized
by potassium permanganate? Write reaction schemes.
4. Write the reaction of 1,2-dilinoeloyl-3-oleoylglycerol formation. Write the reaction of complete
hydrogenation of this fat. Discuss the consistency of fat before and after hydrogenation. Explain your
answer.
5. Write the saponification reaction of tristearin with sodium hydroxide. What are the hydrolysis
products?
6. Write the reaction of phosphatidylserine formation with stearic and linolenic acids. What reaction can
be used to obtain phosphatidylethanolamine from phosphatidylserine?
7. Write the formation reaction of phosphatidylethanolamine, whose hydrolysis yields glycerol,
phosphoric acid, palmitic acid, linoleic acids and ethanolamine. Identify hydrophilic and hydrophobic
parts of the molecule.
8. Write scheme of the reaction of taurine (2-aminoethanesulfonic acid) formation from cysteine. Write
the reaction of taurocholic acid formation.
9. Write the reaction of cholesterol interaction with oleic acid.
10. What vitamin is formed when the ergosterol is exposed to UV light? Write a scheme of this reaction.

Describe the role of oxidative processes involving lipids and their structural components. The concept of
lipid peroxidation; β-oxidation of saturated fatty acids.
Lesson 14
Heterocyclic compounds. Nucleosides, nucleotides. Nucleic acids

- characterize the relation of the structure of heterocyclic compounds with their reactivity;
- characterize the biological significance of heterocyclic compounds and their derivatives;
- describe redox and acid-base properties, electrophilic substitution reactions of heterocycles;
- write tautomeric forms of derivatives of heterocyclic compounds;
- write the structure of nucleosides, nucleotides and nucleic acids.
Bibliography
Required reading:

1. Definition of heterocycles and their classification (according to the nature of the heteroatom; the
number of heteroatoms; the size of the cycle; the degree of unsaturation).
2. Aromaticity of biologically important heterocyclic compounds: pyrrole, furan, thiophene, imidazole,
pyrazole, pyridine, pyrimidine, indole, quinoline, purine.
3. Characteristic of acid-base character of pyrrole and pyridine. Intermolecular hydrogen bond in
imidazole, pyrazole.
4. Reduction reaction of pyrrole and pyridine. The concept of the structure of porphine.
5. Electrophilic substitution reactions of pyrrole, pyridine. Acidophobicity of pyrrole in electrophilic
substitution reactions.
6. Ways of synthesis of nicotinic acid and its amide from β-methylpyridine and nicotine. Nicotinic acid
and its amide (vitamin B3) as a structural unit of coenzymes NAD+ and NADP. Biological role.
7. The specificity of redox reactions of organic compounds. The concept of hydride ion transfer and the
action of the system NAD+ - NADH.
8. Hydroxy derivatives of purine: hypoxanthine, xanthine, uric acid. Structure. Prototropic tautomerism.
Lactim-lactam tautomerism. Salts of uric acid. What acid sites are involved in salt formation?
9. Definition of alkaloids and their classification. The physiological effect of alkaloids. Nicotine,
structure, properties. Nicotine salts formation with organic acids (citric, malic, oxalic, succinic).
Methylated xanthine derivative - caffeine, structure, biological role.
10. Pyrimidine bases: uracil, thymine, cytosine. Purine bases: adenine, guanine. Lactam-lactym
tautomerism.
11. Nucleosides. The nature of the connection of the nucleic base with a carbohydrate. Configuration of
glycosidic center.
12. Nucleotides. The structure of nucleoside monophosphates, diphosphates, triphosphates.
Nomenclature. Macroergic bonds. Biological role. Hydrolysis of nucleotides..
13. Cyclic forms of nucleotides. cAMP and cGMP, their biological importance.
14. Nucleic acids. The general scheme of the structure. Biological role. Ribonucleic (RNA) and
deoxyribonucleic (DNA) acids. Features of their structure. The nature of the connection between
nucleotides in the polynucleotide chain. The concept of the primary structure of nucleic acids: RNA
and DNA. The role of complementary interactions in the biological functions of DNA.

1. What structural features caused the aromaticity of pyrrole, imidazole, pyridine, pyrimidine, purine?
Huckel's aromaticity rule.
2. Show the formation of intermolecular hydrogen bond on the example of imidazole.
3. Write the reaction: (a) pyrrole with sodium amide; (b) pyridine with hydrochloric acid. What
properties does pyrrole and pyridine show in these reactions?
4. Features of the reactions of pyrrole and pyridine reduction. Write the reactions and name the products.
5. Write the electrophilic addition reactions: 1) pyrrole iodination; 2) pyridine sulfonation; 3) pyridine
nitration. What are the reaction products? What anti-vitamins does the pyridine sulfonation product
include?
6. Write the scheme of the following transformations: nicotine → nicotinic acid → nicotinamide. What
group of vitamins does nicotinic acid and its amide belong to? Name the type of each reaction.
7. Gout inflammatory processes are caused by sedimentation of the uric acid monosodium salt in the
joints. Which tautomeric form of uric acid does participate in the sodium salt formation reactions?
Write the reaction of sodium hydrogen urate and sodium urate formation.
8. Nicotine is found in tobacco leaves in the form of salts of organic acids. Write the reaction of nicotine
salt formation with citric acid. Which of the basic centers of the nicotine molecule is stronger and
involved in salt formation?
9. Write lactam-lactim tautomerism transformations of uracil and guanine. In which tautomeric forms do
pyrimidine and purine bases participate in nucleotide formation? Why?
10. Write the reaction of formation 5’-thymidylic acid (dTMP) and 5’-guanylic (GMP) acid.
11. Write the formation reaction of the following compounds: adenosine-5’-phosphate (AMP), ADP,
ATP. Macroergic bonds. Biological importance.
12. Write the reaction of cGMP formation (guanosin-3’, 5’-cyclophosphate).
13. * Draw a diagram of the connection of nucleotides in the polynucleotide chain using as an example of
dAMP (deoxyadenosine-5-phosphate) with dCMP (deoxycytidine-5-phosphate). What nucleic base
does form a complementary pair with cytosine in a DNA helix? How many hydrogen bonds are
formed between them?
14. * Which of the two complementary pairs - UMP and AMP, or TMP and dAMP - is part of the DNA?
Write the structure of the selected pair and show the hydrogen bonds. What atoms form hydrogen
bonds?
Class format:
number of mastered practical skill No. 1,2,3,4
Assessment:
1. 1) Name the given compounds
N
N N N
N 2) N 3) H 4) H 5) H
2) Choose a compound with the most acidic properties. Explain and write a reaction proving the acidic
properties of chosen compound. Name the product of the reaction.
3) Choose compounds with aromatic properties. Explain your choice.
2. Write the following reactions:
a) pyridine
b) pyrrole
c) pyridine
d) pyrrole
e) pyridine
f) pyrrole + NaNH2 →
g) pyridine + Н2О →
3. Write the scheme of the following reactions: β-methylpyridine→nicotinic acid→nicotinamide. Which
group of vitamins does nicotinic acid and its amide belong to? Name the type of each reaction.
4. The structure of caffeine and nicotine. Write the nicotine salt formation reaction with malic acid (2-
hydroxybutanedioic acid).
Which of the following statements are consistent with the structure and properties of adenosine - 3', 5'
- cyclophosphate:
1) two molecules H3PO4 are formed after its hydrolyses in an acidic medium
2) it has an N-glycosidic bond which is resistant to acid hydrolysis
3) contains two ester bonds with phosphoric acid in its structure
4) contains two anhydride bonds in its structure
5) β-D-ribose is in the structure
6. Write schemes of prototropic and lactim-lactam tautomerism of xanthine (2,6-dihydroxypurin).
7. Write tautomeric forms of uric acid. In what tautomeric form is uric acid involved in sodium salt
formation reactions? Write the reaction of salt formation of uric acid with one and two sodium
hydroxide molecules.
8. Give a diagram of the lactim-lactam tautomerism of cytosine (4-amino-2-hydroxypyrimidine).
9. Which base is complementary to guanine (2-amino-6-hydroxypurin)? Give the structure of this
complementary pair and indicate hydrogen bonds. Between which atoms do they arise?
10. Write the reaction for the formation of dCPM (cytidine-5’-phosphate). Indicate the types of bonds and
their relation to hydrolysis.
11. Write down the reaction of cAMP formation (adenosine-3’, 5’-cyclophosphate). Indicate types of
bonds and their relation to hydrolysis.
12. Write the reactions of the formation of ATP (adenosine-5’-triphosphate). Indicate the types of bonds
and their relation to hydrolysis. Macroergic connections. Biological value.

Describe the biochemical reactions involving the coenzyme NAD + -NADH. Give examples of reactions
involving this coenzyme.
Lesson 15
Metabolic reactions of biologically active compounds. Midterm 2

- describe the biological role of biologically important compounds;
- solve situational problems that simulate physicochemical processes in living organisms, based on
theoretical principles;
- to predict the results of physicochemical processes in living systems, based on theoretical principles;
- to characterize the relationship of the physical and chemical properties of substances, as well as their
chemical structure with their biological activity in a living organism.
Bibliography
Required reading:

1. Specific metabolic functions. Catabolism. Anabolism.
2. Metabolic reactions and features of their course in the body:
1) decarboxylation reaction;
2) deamination reaction;
3) acylation reaction;
4) alkylation reaction;
5) condensation reaction;
6) acid-base reactions;
7) redox reaction (NAD +, NADH);
8) an esterification reaction (fat synthesis, glucose phosphorylation, esterification with coenzyme A);
9) hydrolysis reaction (peptides, proteins; di- and hemisaccharides; nucleotides; triacylglycerols,
phosphoglycerides);
10) hydration reactions, dehydration.
3. The scheme of metabolic transformations of pyruvic acid. Chemism of metabolic reactions of pyruvic
acid conversion.
4. The concept of the tricarboxylic acid cycle (Krebs cycle). Chemistry of metabolic reactions in the Krebs
cycle.

22. *Write the following reactions:
1)
2)
3)
4)
5)
2. Write acid hydrolysis reactions:

1) triolein
2) cytidylic acid
3) Glu-Cis-Gly tripeptide
4) lactose
5) phosphatidic acid
3. Name the products of the reactions.
1) phosphorylation of β-D-glucopyranose
2) acylation of β-D-galactosamine to N-acetyl-β-D-galactosamine
To prepare for midterm control:

Use questions given for each lesson on all topics covered.
Class format:
Assessment: Midterm. Summative (written control, set on the basis of solving problems/cases)
1. Write the following reactions:
1) esterification of acetic acid with coenzyme A
2) hydration of fumaric acid
3) decarboxylation of oxaloacetic acid
4) oxidative deamination of alanine
5) non-oxidative deamination of aspartic acid
6) dehydrogenation of malic acid
7) reduction of acetoacetic acid
8) lactic acid oxidation
9) keto-enol tautomerism of oxaloacetic acid
10) alkylation of ethanolamine to choline
11) acylation of ethanolamine to acetylcholine
12) condensation of oxaloacetic acid with acetyl coenzyme A
13) β-D-glucopyranose phosphorylation
14) acylation of β-D-galactosamine to N-acetyl-β-D-galactosamine
Name the products of the reactions.
3. Write acidic hydrolysis reactions:
1) tripalmitin
2) deoxyadenyl acid
3) Tyr-Gly-Gly-Phe-Leu
4) sucrose drolysis
5) phosphatidic acid
What are the reaction products?.

Characterize specific metabolic functions. Describe matabolic and anabolic reactions.
Appendix 1
ASSESSMENT SHEETS
ASSESSMENT SHEET
case study solution
Name of the student ____________________ group number ________________________
№ Step Evaluation Criteria Excellent Acceptable Correction Unacceptable

required
1 Theoretical knowledge was 10 7 5 0
applied in solving the
problem; reference literature
was used if necessary
2 The formulas necessary for 10 8 5 0
solving the problem and / or
definition are correctly written
3 The correct algorithm for 10 8 5 0
solving the problem
4 The course of solving of the 20 15 10 0
problem is explained in detail
and sequentially
5 The necessary calculations are 10 8 5 0
performed correctly
6 The units of used and 10 7 5 0
calculated values are indicated
correctly
5 The biological role of the 10 7 5 0
compound is correctly
characterized and / or the
mechanism of action of the
buffer solution is recorded
6 A reasoned analysis is carried 10 7 5 0
out and reasonable
conclusions are made
7 Chemical terminology 10 8 5 0
knowledge
In total 100 75 50 0
ASSESSMENT SHEET
task according to the schemes of organic reactions

required
1 All formulas of organic 20 15 10 0
compounds are correctly
written
2 All reaction equations are 40 30 20 0
correctly written
3 The starting materials and 10 8 5 0
chemical reaction products are
correctly named
4 The correct reagents for this 10 8 5 0
reaction were chosen
compound and / or the
structure of the reaction
product is characterized
correctly
knowledge
In total 100 75 50 0
ASSESSMENT SHEET
oral (written) survey

required
1. Understanding the topic at 20 15 10 0
the proper level
2. Full and correct answer to 20 15 10 0
questions
3. Compliance of the answer 15 12 7 0
to the questions posed
4. Examples and evidence to 15 12 8 0
support the response
6 Reasoned analysis and 20 15 10 0
correct conclusions from
the information provided
knowledge
In total 100 75 50 0
ASSESSMENT SHEET
midterm

required
1. Level of the topic 20 15 10 0
understanding
2. Drawing up a complete 20 15 10 0
and correct answer
based on the material
studied
3. Compliance of the 15 12 7 0
material with the
questions posed
4. Confirmation of the 15 12 8 0
answer with specific
examples and facts, the
ability to use reference
literature if necessary
6 The ability to 20 15 10 0
independently and
reasonably analyze and
draw sound conclusions
7. Chemical terminology 10 6 5 0
knowledge
In total 100 75 50 0
ASSESSMENT SHEET
of exam

required
1 Theoretical are applied 10 7 5 0
knowledge in solving of the
problem
2 The formulas to solve the 10 8 5 0
problem and / or definition
are written correctly
3 The algorithm for solving the 10 8 5 0
problem is chosen correctly
4 The course of solving the 10 8 5 0
problem and gave a
theoretical justification is
explained in detail and
consistently
compound is characterized
correctly and / or mechanism
of action of the buffer
solution is written correctly
6 All the formulas of organic 20 15 10 0
compounds are written
correctly; correct names of
organic compounds are given
7 All the reaction equations are 20 15 10 0
written correctly
compound and/or the
structure of the reaction
product are characterized
correctly
In total 100 75 50 0

SYLLABUS GM 2019-20 English

Uploaded by

Copyright:

Available Formats

You might also like

SYLLABUS GM 2019-20 English

Uploaded by

Document Information

Original Description:

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

SYLLABUS GM 2019-20 English

Uploaded by

Copyright:

Available Formats

«С.Ж.

АСФЕНДИЯРОВ АТЫНДАҒЫ ҚАЗАҚ ҰЛТТЫҚ МЕДИЦИНА УНИВЕРСИТЕТІ» КЕАҚ

Information about teachers

Policy of the discipline:

▪ appellate for examination assessment in the prescribed manner.

Dress Code Requirements

Purpose of the course unit

Brief description of the discipline

Learning outcomes of the course unit

The study of this discipline is based on knowledge of the following disciplines:

Plan for studying the discipline

Type of % Learning Outcome Assessment Forme

Final FA= The minimum score of a

Assessed Learning Outcomes

The list of tasks to achieve the learning outcomes:

List of practical skills

Macro- and microelements: biological role, medical applying

After the lesson the student will be able to:

Questions of the lesson:

Class format: Discussion of tasks and situational tasks.

Tasks and exercises for discussion on practical lessons:

First, organizational issues and discipline policies are discussed..

Assessment: in the form of feedback during the consultation

Elements of chemical thermodynamics and kinetics.

After the lesson the student will be able to:

Questions of the lesson:

Class format: Discussion of tasks and situational tasks.

Assessment: Formative (in the form of feedback; can be improved)

Tasks and exercises for discussion on practical lessons:

Assessment: in the form of feedback during the consultation

Solutions: composition and colligative properties.

After the lesson the student will be able to:

Questions of the lesson:

Class format: Discussion of tasks and situational tasks.

Tasks and exercises for discussion on practical lessons:

Assessment: in the form of feedback during the consultation

Protolytic equilibria and processes. Buffer solutions

After the lesson the student will be able to:

Questions of the lesson:

Class format: Discussion of tasks and situational tasks.

Tasks and exercises for discussion on practical lessons:

2. Calculate concentration of hydrogen-ions [H+], when hydroxide-ions concentration [OH-] (mole/l) is

Assessment: in the form of feedback during the consultation

Heterogeneous and metal-ligand equilibria. Complex compounds

After the lesson the student will be able to:

Questions of the lesson:

Class format: Discussion of tasks and situational tasks.

Tasks and exercises for discussion on practical lessons:

Assessment: in the form of feedback during the consultation

Physical chemistry of surface phenomena. Chromatography

After the lesson the student will be able to:

Questions of the lesson:

Class format: Discussion of tasks and situational tasks.

Tasks and exercises for discussion on practical lessons:

Г, mmole/g 0.44 0.78 1.04 1.44

Assessment: in the form of feedback during the consultation

After the lesson the student will be able to:

Name of the student group number ____

Name of the student group number ____

Name of the student group number ____

Name of the student group number ____

Name of the student group number ____