1. ORGANIC CHEMISTRY 2 Prof. Janina E. Kamińska
Łódź University of Technology
Faculty of Biotechnology and Food Sciences
Institute of General Food Chemistry
ul. Stefanowskiego 4/10
Room no 209
(Consultation hours: Tue. 13:15-14:00, Wed. 14:15-15:00)
Phone: 1

2. Lecture 15 h Tutorials 15 h Laboratory 45 h
ORGANIC CHEMISTRY 2 sem. III. 2018/19
Lecture 15 h
Tutorials 15 h
Laboratory 45 h
Prof. J.E. Kamińska, dr Ewa Maciejczyk
Workload outside classroom 90 h
ECTS credits: 6

3. Textbooks
John McMurry, “Organic Chemistry”, 5th ed. Brooks/Cole Publishing Co., Pacific Grove, California 2000 (or later editions)
K. P. C. Vollhardt, N. E. Schore, “Organic Chemistry, Structure and Function”, 3rd ed. W. H. Freeman and Co., New York 1999 (or later editions)
J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford University Press 2000 (or later editions)
Laboratory textbooks:
J.R. Mohrig, C. Noring-Hammond, P.F. Shatz ”Techniques in Organic Chemistry”
W.H. Freeman and Company 2010
J.C. Gilbert, S.F. Martin ”Experimental Organic Chemistry” 5th ed. Brooks/Cole 2011
L. M. Harwood, C. J. Moody, J. M. Percy, “Experimental Organic Chemistry”, 2nd ed., Blackwell Science Ltd., Oxford 1999

4. Biological Applications
Textbooks
Organic Chemistry
with
Biological Applications
Organic Chemistry
Fundamentals
of Organic Chemistry

5. McMurry in Polish

6. Laboratory textbook

7. Final grade consist of:
Written exam test 50%
Laboratory grade 30%
Organic chemistry 1 20%

8. Lectures An overview of carbonyl group chemistry
Aldehydes and ketones – preparation and chemical reactions: nucleophilic addition to carbonyl group; -substitution reactions, carbonyl condensation reactions (aldol condensation).
Carboxylic acids and their derivatives (acyl chlorides, anhydrides, esters, amides, nitriles) – preparation and chemical behaviour (nucleophilic acyl substitution, -substitution reactions).
Aliphatic and aromatic amines - preparation and chemical properties.

9. Biomolecules
-Amino acids – structure and properties. Isoelectric point, analytical reactions of amino acids.
Peptides and proteins. Peptide structure determination. Chemical synthesis of peptides. Protein structure (general).
Monosaccharides (pentoses and hexoses) – structure and properties.
Disaccharides (sucrose, lactose, maltose, cellobiose) and polysaccharides (cellulose, starch, glycogen) – structure and properties.
Lipids – structure and properties of glycerides, isoprenoids, terpenes.
Heterocyclic compounds containing oxygen, sulphur and nitrogen. Pyrimidine and purine bases – structure and properties. Nucleotides, nucleosides and nucleic acids structure.

10. of carbonyl group chemistry
An overview
of carbonyl group chemistry

11. CARBONYL GROUP sp2      sp2 sp2      sp2
C=O bond length A
C=C bond length A

12. CARBONYL GROUP ELECTRONIC STRUCTURE
Lone-pair electrons -
Lone-pair electrons
π-bond +
Carbon
or Hydrogen
Carbon
or Hydrogen

13. CARBONYL GROUP ORBITALS

14. POLARIZATION OF CARBONYL GROUP AND ITS REACTIVITY
Nucleophilic oxygen reacts
with acids and electrophiles - +
Electrophilic carbon reacts
with bases and nucleophiles

15. TYPES OF CARBONYL COMPOUNDS
ALDEHYDES
Hydrogen or carbon
cannot stabilize
negative charge and
therefore cannot act
as leaving group
KETONES

16. TYPES OF CARBONYL COMPOUNDS
Carboxylic acid
Carboxylic acid chloride
Carboxylic acid anhydride
Carboxylic acid ester
Carboxylic acid amide
Electronegative atom (oxygen, halogen, nitrogen) bonded to acyl group
R-CO- can stabilize a negative charge, therefore groups –OH, -Cl, -OCOR’,
-OR’, -NH2 can serve as leaving groups in substitution reactions.

17. TYPES OF CARBONYL COMPOUNDS
Cyclic acid anhydride
Cyclic ester
(lactone)
Cyclic amide
(lactam)

18. POLARITY OF CARBONYL COMPOUNDS
Type of carbonyl group
Dipole moment
(D)
HCHO
CH3CHO
(CH3)2CO
PhCOCH3
Cyclobutanone
CH3COOH
CH3COCl
CH3COOCH3
CH3CONH2
CH3CON(CH3)2
Aldehyde
Ketone
Carboxylic acid
Acid chloride
Ester
Amide
2.33
2.72
2.88
3.02
2.99
1.74
1.72
3.76
3.81

19. TYPES OF CARBONYL COMPOUNDS REACTIONS
GENERAL MECHANISMS
Nucleophilic addition
Nucleophilic acyl substitution
-Substitution
Condensation reactions

20. Nucleophilic addition to carbonyl group
1st step
Carbonyl carbon
rehybridizes
from sp2 to sp3

21. Nucleophilic addition to carbonyl group
2nd step
Two ways of stabilization
of tetrahedral intermediate

22. Nucleophilic addition to carbonyl group
EXAMPLE 1 – addition of methylmagnesium bromide to cyclohexanone
Synthesis of tertiary
alcohol from ketone

23. Nucleophilic addition to carbonyl group
EXAMPLE 2 – cyclohexanone imine formation
Net effect – replacing
C=O by C=NR

24. Nucleophilic acyl substitution
Net effect – replacing of group Y with nuclephile.
-Y is called leaving group
Y = -OR (ester)
-OCOR (anhydride)
-Cl (acid chloride)
-NH2, -NHR, -NR2 (amide)

25. Nucleophilic acyl substitution
EXAMPLE – ester synthesis from acid chloride and alkoxide
Net effect – replacing
of Cl by OR

26. -Substitution reactions -substituted carbonyl compound
Intermediates

27. -Substitution reactions
Net effect – extending of carbonyl compound hydrocarbon
framework by –CH2R fragment at -carbon

28. -Substitution reactions
EXAMPLE – -methylation of cyclohexanone

29. Carbonyl condensation reactions
New C-C bond
Two aldehydes
Aldol product
(aldehyde + alcohol)

30. Carbonyl condensation reactions
Carbonyl condensation reaction is a combination of -substitution step
and nucleophilic addition step
acetaldehyde
By condensation of acetaldehyde
3-hydroxybutanal is prepared
3-hydroxybutanal

31. Nucleophilic addition reactions of carbonyl compounds
Alcohol
Alcohol
Cyanohydrin
Alkene
Imine
Alkane
Acetal
Enamine

32. Negatively charged nucleophiles
Neutral nucleophiles
Hydroxide ion
Hydride ion
A carbanion
An alkoxide ion
Cyanide ion
Water
An alcohol
Ammonia
An amine