1. TASHKENT MEDICAL ACADEMY Department of Bioorganic and Biological Chemistry Bioorganic chemistry I COURSE SUBJECT : Reactivity of organic CONNECTIONS. Reactions of radical substitution and electrophilic addition. Electrophilic substitution reactions. LECTURE №3 LECTURER : PROFESSOR A.D.DZHURAEV

2. Knowledge of the reaction to form of organic compounds as a basis for understanding the reactions occurring in the body

3. 1. Types break the covalent bond. 2. Types of organic reactions 3. Radical substitution reaction 4. Electrophilic addition reactions 5. Electrophilic substitution reactions in the aromatic ring 6. Orienting effect of substituents on the aromatic ring 7. Electrophilic substitution reactions occurring in the body

4. 1) Homolytic (HOMO - equal, identical) high gas phase, nonpolar. environment RADICAL reagent (RADICALS) - Free Radicals А׳ - В׳

5. polar solvent

6. :Nu - - Nucleophilic particles, negatively charged, has electronic pair through which make a new relationship.

7. 1. Homolytic or the free-radical 2. Heterolytic or ion - in these reactions as an intermediate particle participate carbocations and carbanions. 3. Synchronous (AGREED). In these reactions, the oldest and gap formation of new connections occur simultaneously. cyclohexane

8. reactionradicalnucleophilicelectrophilic substitution (S) connection (A) expansion (E) SRARERSRARER SNANENSNANEN SEAEEESEAEEEE

9. Electrophilic addition reaction(АE ) I. Accession halogens 1,2 - dibromoethane

10. 1) Education  -Complex 2) Transition  - Complexto  -Complex 3) Nucleophilic Attack  - Complex or  -complex Cyclical. ion or brom  -complex 1,2-dibromoethane

11. 1)1.2 - dibrombuten -3 3) 3 - chlorobutyl -1 2) 1.4 - dibrombuten -2 4) 1 - chlorobutyl -2

12. О СН 2 = СН – С + НСl ОН О СН 2 – СН 2 – С Cl ОН ++ ++ -- -- acroleic acid 3 - Chlorine propanoic acid

13. 3-chlorobutyl-1 1-chlorobutyl-2

14. propene - (methylacetylene) 2-chloropropane-1 2,2-dichloropropene

15. 1. education electrophilic particles: polarization molecule gap connection 2. TRANSITION  -COMPLEX IN  -COMPLEX :  -COMPLEX  - COMPLEX hybridized 3. The cleavage of a proton from  -COMPLEX: The reaction mechanism:

16. Polarization or break bonds in molecules Cl 2 under Lewis acid (AlCl 3,FeCl 3 ) :  - complex  - complex 1 STAGE : 2 STAGE : 3 STAGE :

18. Vice-I-kind - showing the effect of M + (halogens, ОН, NH 2, SH, OR) – increase the electron density in the benzene ring, increase the reaction rate and send a new group in the ortho position pair : NH 2.. -- -- -- -- -- Aniline М(+) Phenol М(+) ОН.. --

19. Vice-II-type-M showing the effect of (COOH, CHO, NO 2, SO 3 H) – reduce the electron density in the benzene ring, the rate of reaction and direct the new group in the meta position : C O H O O N ++ -- -- ++ ++ nitrobenzene М(-) benzoic aldegid М(-) ++ ++ -- -- ++

20.  -tiofensulfo acid  - nitrofuran 5-nitrofurfurol  -nitropyridine