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Year 1 · Medicine · Medical University of Sofia

Medical Chemistry: notes and exam prep for MU Sofia

Medical Chemistry for Year 1 Medicine at the Medical University of Sofia: all 43 syllabus topics in 16 sections, with exam-focused notes and SuperPrep recall sets.

What Medical Chemistry has on SuperMed

  • Notes on every topic, written to answer the syllabus question as it is asked.
  • SuperPrep : 448 recall sets. A short piece of material, then questions on all of it from memory, at the grade you are aiming for.

The Medical Chemistry syllabus

Every topic, numbered as the department numbers it. Each line says what the topic covers.

1. Chemical bonding and structure of molecules4 topics

  1. 1.1Nature of chemical bondingCovalent bond. Valence bond theory: σ- and π-bonds, single and localized double and triple bonds. Hybridization of atomic orbitals –nature and types. Saturation and direction of covalent bond. Coordinate covalent bond - (Dative bond). Delocalized covalent bond. Cyclic and acyclic conjugated systems. Polar and non-polar covalent bonds.Degree of ionicity. Ionic bond.
  2. 1.2Basic characteristics of molecules – geometry of the molecules, bond angles, length and energy of the chemical bonds and dipole momentNon-covalent interactions. Inter- and intramolecular forces. Hydrogen bond, ionic and Van der Waals interactions: dipole-dipole interactions (Keesom force), dipole – induced dipole interactions (Debye force) and induced dipole – induced dipole interactions (London dispersion forces). Biological meaning of the non-covalent interactions.
  3. 1.3Electronic effects in organic moleculesInductive and mesomeric effects. Resonance structure. Reactions types according to the structural change in reagent molecules. Reaction of addition (coupling), elimination (decomposition), substitution, rearrangement (isomerization) and oxidation-reduction reactions. Examples. Types of reagents – radicals, nucleophiles and electrophiles. Activation energy. Activated complex and transition state. Complex chemical reactions – competitive (parallel), successive, reversible and chain reactions. Heat of chemical reactions.
  4. 1.4IsomerismConstitutional (chain and positional) isomerism. Stereo isomerism. Configurational isomerism. Enantiomerism of compounds with chiral centers. Fischer projections and wedge – and - dash structural formulas. Sigma - diastereomerism of molecules with more than chiral centers. Epimers. Pi - diastereomers (geometric isomerism). Conformational isomerism. Newman projection formulae. Basic types of conformations.

2. Dispersions2 topics

  1. 2.1Types of dispersionsMolecular and ionic solutions. Mechanism of dissolution. Solubility and concentration of solutions. Temperature dependence of solubility. Solutions of electrolytes. Dissociation constant and degree of electrolyte dissociation. Weak and strong electrolytes. Ostwald's dilution law.
  2. 2.2Colloid dispersed systemsClassification. Kinetic and optical properties of colloids. Macromolecular Solutions. Stability and coagulation of colloidal solutions. Biological significance. Colligative properties of diluted solutions. Vapor pressure, boiling point elevation and freezing point depression. Diffusion, osmosis and law of osmotic pressure. Biological significance.

3. Chemical kinetics and thermodynamics4 topics

  1. 3.1Chemical kineticsChemical reaction rate. Concentration dependence on the reaction rate. Kinetic equation. Rate constant. Reaction order. Zero, first and second order reactions. Molecularity of the reaction. Rate - determining step. Temperature dependence on the rate of a reaction. Arrhenius equation. Other main factors that can affect the reaction rate of a chemical reaction.
  2. 3.2CatalysisCatalysts. Principle of catalystaction. Homogeneous and heterogeneous catalysis. Mechanism of catalytic reactions. Autocatalysis. Factors affecting the catalytic process. General concept for biocatalysis.
  3. 3.3Chemical thermodynamicsThermodynamic quantities: enthalpy, entropy and free energy. Heat of the chemical reaction. Reversible and irreversible chemical reactions. Chemical equilibrium. The rate law. Equilibrium constants for homogeneous, heterogeneous and successive reactions. Free energy and chemical equilibrium. Criteria for determining the direction of spontaneous processes - exergonic, endergonic and anergonic reactions.
  4. 3.4Reaction isotherm of van't HoffLe Chatelier - Brown principle. Effect of changes in the reaction conditions (temperature, concentration and pressure) on equilibria. Predicting the direction of a reversible reaction. Conjugation reactions in biochemistry. Compounds with „macroergic“ bonds.

4. Equilibrium processes in solutions4 topics

  1. 4.1Protolytic reactions(Protolysis). Acids and bases. Classical concept of acid and bases - Arrhenius theory. Theory of Broensted - Lowry for acids and bases. Strength of acids and bases. Acid and base ionization constants. рКаand рКb. Factors, affecting the strength of acids and bases. Theory of Lewis.
  2. 4.2AutoprotolysisIon product constant of water. pH concept (рН). Relationship between temperature and ion product constant of water. Importance of pH homeostasis in body fluids. Methods for pH measurement and biological significance.
  3. 4.3HydrolysisQuantitative characteristics - degree of hydrolysis and hydrolysis constant. Hydrolysis of salts formed of weak electrolytes. Relationship between hydrolysis constants and ionization constants. Hydrolysis of organic compounds. Biological meaning of hydrolysis.
  4. 4.4Buffer solutions – definition, propertiesHenderson - Hasselbalch equation. Buffer capacity. Preparing a buffer solution with a specific pH. Biological meaning of buffers. Buffers of the blood.

5. Oxidation-reduction (redox) processes2 topics

  1. 5.1Chemical redox processesElectron transfer. Half-reactions. Electrochemical redox potential. Standard electrode potential. Standard hydrogen electrode. Chemical current sources. Galvanic and electrolytic cell. Electrolysis.
  2. 5.2Potential concentration dependenceNernst - Peters equation. Formal electrode potential (Еh). Criteria for predicting the direction of redox reactions. Biological oxidation.

6. Complex compounds1 topics

  1. 6.1Complex (coordination) compoundsCentral ion, ligands and coordinative number. Coordinate covalent bond (Dative bonds). Types of ligands - denticity. Chelate complexes. Positively charged, negatively charged and neutral complex ions. Nomenclature, structure and stability of complex compounds. Biological significance. Application in medicine.

7. Hydrocarbons2 topics

  1. 7.1Aliphatic hydrocarbonsChemical bonding and hybridization models. Nomenclature. Homologous series. Isomerism: constitutional isomers (chain and positional). Conformation of cyclohexane. Axial and equatorial substitutes. Chemical properties of alkanes, alkenes and alkynes. Characteristic types of reactions. Mechanism of radical substitution (SR). Electrophilic addition reaction (АE). Polymerization of alkenes. Oxidation and combustion.
  2. 7.2Aromatic hydrocarbons (Arenes)Aromaticity–Hückel’s rule. Reactions of electrophilic substitution (SEAr). Orientation in benzene ring. Activating and deactivating groups. Polycyclic aromatic hydrocarbons. Procarcinogens.

8. Alcohols and Phenols. Thiols1 topics

  1. 8.1Alcohols and phenolsStructure and nomenclature. Homologous series. Types of alcohols and phenols. Acid – Base properties. Chemical properties of alcohols. Esterification, nucleophilic substitution (SN) – reaction with hydrogen bromide. Oxidation. Reactions of phenols. Acylation, nitration and bromination. Thiols – structure and properties. Some important naturally occurring thiols.

9. Amines and amino alcohols2 topics

  1. 9.1Aliphatic and aromatic aminesStructure, nomenclature and acid-base properties. Order of basicity of amines. Chemical properties. Reactions with nitric acid, formation of azo compound (diazenes), electrophilic substitution in the aromatic ring of anilines. Reactions with aldehydes, ketones, carboxylic acids and carboxylic acids functional derivatives.
  2. 9.2Biogenic amines - definition and classificationMonoamines derived from 2-phenylethylamine - catecholamines. Medicinal substances derived from 2-phenylethylamine. Polyamines - putrescine, cadaverine, spermidine, spermine. Amino alcohols - colamine (ethanolamine), choline, sphingosine.

10. Carbonyl compounds. Aldehydes and ketones2 topics

  1. 10.1Aldehydes and ketonesStructure and nomenclature. Tautomerism. Nucleophilic addition (AN) reactions. Reaction with oxygen nucleophiles (water and alcohols). Nucleophilic substitution reaction (AN + DN). Reactions with nitrogen nucleophiles (ammonia, primary amines, hydrazine and phenylhydrazine).
  2. 10.2Reaction of carbonyl compounds with carbon nucleophiles (aldol reaction and aldol condensation)Role for biological processes. Oxidation-reduction processes. Reduction of aldehydes and ketones. Oxidation of aldehydes. Quinones. Ubiquinones (coenzyme Q10), vitamin K1 (phylloquinone)

11. Carbonyl compounds. Carboxylic acids5 topics

  1. 11.1Mono carboxylic acidsSaturated and aromatic carboxylic acids. Structure and nomenclature. Relationship between structure and acidity. Chemical properties. Nucleophilic acyl substitution reactions (AN + DN): esterification and anhydrides formation. Alkaline hydrolysis (saponification) of esters and Claisen condensation. Reaction of esters with amines. Relationship to ribosomal protein synthesis. Acid hydrolysis of amides. Amides as drugs: paracetamol and lidocaine.
  2. 11.2Unsaturated mono carboxylic acidsStructure and nomenclature. Representative unsaturated mono carboxylic acids: acrylic acid, methacrylic acid and oleic acid. Chemical properties. Electrophilic addition of hydrogen bromide and polymerisation. Polyunsaturated fatty acids. Eicosanoids. Non-steroidal anti-inflammatory substances - aspirin, ibuprofen. Prostaglandin biosynthesis inhibition.
  3. 11.3Saturated dicarboxylic acidsStructure and nomenclature. Representative saturated dicarboxylic acids: oxalic, malonic, succinic, glutaric and adipic acids. Chemical properties. Decarboxylation and formation of cyclic anhydrides. Unsaturated dicarboxylic acids. Structure and nomenclature. Representative unsaturated dicarboxylic acids: maleic and fumaric acid. Chemical properties. Aromatic dicarboxylic acids: phthalic, isophthalic and terephthalic acid. Chemical properties.
  4. 11.4Hydroxycarboxylic acids (aliphatic and aromatic acids)Structure, nomenclature and acidity. Stereoisomerism in saturated hydroxy carboxylic acids. Major examples: lactic acid, β-hydroxy butyric acid, malic acid, tartaric acid, citric acid and salicylic acid. Chemical properties. Reactions on heating and complex formation. Medicines derived from salicylic acid.
  5. 11.5Oxo carboxylic acidsStructure and nomenclature. Major examples: glyoxalic, pyruvic, acetoacetic and oxaloacetic acid. Keto-enol tautomerism. Chemical properties. Addition of water, decarboxylation and oxidation. Acids involved in the Krebs cycle. Ketone substances ("ketone" bodies) - biological significance.

12. α-Amino acids, peptides and proteins3 topics

  1. 12.1α-Amino acids - structure, nomenclature, stereochemistryEssential amino acids. Acid-base properties. Isoelectric point. Chemical properties. Esterification, acylation and interaction with formaldehyde and ninhydrin. Amino acid analysis - diagnostic significance.
  2. 12.2Peptides and proteinsPeptide bond structure and stereochemistry. Methods for peptide synthesis - protecting groups and solid-phase synthesis. Examples of biologically important peptides: glutathione, enkephalin, vasopressin, oxytocin and insulin.
  3. 12.3Structural organisation of proteinsStructural elements of primary, secondary, tertiary and quaternary structure. Structure-function relationship. Edman method of protein sequencing. Methods for establishing the tertiary structure of proteins. Proteomics.

13. Carbohydrates3 topics

  1. 13.1Carbohydrates - definition and nomenclatureMonosaccharides - definition, structure and isomerism (constitutional isomers, enantiomers, diastereomers, epimers). Hemiacetal (cyclic) forms of monosaccharides - Haworth structures, anomers. Mutarotation.
  2. 13.2Chemical properties of monosaccharidesGlycoside bond formation. Isomerism of the glycosidic bond. Oxidation reactions (formation of ofaldonic, aldaric (sugar) and uronic acids). Reaction with primary amino group compounds. Reactions for detection of the structure of monosaccharides. Biologically important esters (esters with phosphoric acid).
  3. 13.3Disaccharides and polysaccharidesSpatial characteristic of glycosidic bond. Reducing and non-reducing disaccharides. Representative disaccharides: maltose, cellobiose, lactose and sucrose. Homopolysaccharides: starch, glycogen, cellulose, β-glucans and chitin - structure and properties. Heteropolysaccharides: hyaluronic acid, chondroitin sulphate, pectins and heparin - structure and properties. Glycoproteins - types. Biological significance of glycosylation.

14. Nitrogen-containing heterocyclic compounds3 topics

  1. 14.1Heterocyclic compounds with one heteroatom. PyrrolePyrrole. Structure. Acid-base properties and reaction with halogens (bromine or iodine). Compounds containing a porphyrin ring: protoporphyrin, haeme and haemin. Haemoglobin and methaemoglobin. Indole (benzopyrrole). Tryptophan. Neurotransmitters - serotonin and melatonin.
  2. 14.2Heterocyclic compounds with one heteroatom. PyridinePyridine. Structure and acid-base properties. Electrophilic substitution reactions (bromination and nitration). Nucleophilic substitution reactions (reaction with sodium amide). N-Alkylation (reaction with iodomethane). Nicotinamide (vitamin B3), nicotinamide adenine dinucleotide and vitamin B6 - structure and biological significance. Nicotine.
  3. 14.3Heterocyclic compounds with two nitrogen atomsImidazole (1,3-diazole). Structure and acid-base properties. Tautomerism in imidazolederivatives. Histidine and histamine. Antihistamines. Pyrimidine (1,3-diazine). Structure and acid-base properties. N-Alkylation (reaction with iodomethane). Pyrimidine bases: cytosine, uracil and thymine. Purine. Structure. Purine bases - adenine and guanine. Caffeine.

15. Nucleic acids1 topics

  1. 15.1Nucleic acidsNucleotides - acid-base properties and tautomerism. Spatial characteristic of RNA and DNA - complementarity. DNA denaturation. Polymerase chain reaction. Sanger method of DNA sequencing. Recombinant technologies. Genomics.

16. Lipids4 topics

  1. 16.1Lipids - definition and classificationsKetoacyl lipids. Long chain fatty acids. Fats - structure and properties. Oxidation. Saponification of fats. Glycerophospholipids - structure, types and biological significance. Sphingosine and sphingophospholipids - structure and biological significance.
  2. 16.2Isoprene and isoprenoid lipidsStructure and nomenclature. Acyclic and cyclic terpenes. Carotenoids. Fat-soluble vitamins (A, E and K) - biological functions.
  3. 16.3Isoprenoid lipids. SteroidsSteroids - definition, structure and classification. Cholesterol - biological synthesis. Cholesterol transport complexes. Statins. Vitamins of group D - biological function.
  4. 16.4Isoprenoid lipids. Sex hormonesSex hormones. Contraceptives. Anabolicsteroids. Corticosteroids - mineralocorticoids and glucocorticoids.

Who writes it

Each topic is drafted by a senior student against the syllabus question, sourced from the department’s lectures and textbook, and checked line by line by a second student before it is published. It is exam study support, not clinical guidance, and SuperMed is not affiliated with the university. How content is made

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