1. ORGANIC CHEMISTRY 1 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: Wed. 11:15-12:00, Fri. 14:15-15:00)
Phone:

2. ORGANIC CHEMISTRY 1 sem. II. 2018/19
Lecture 30 h
Tutorials 15 h
Workload outside classroom 75 h
ECTS credits: 4

3. Final grade consist of:
13 June 2019: written tutorials test 50%
8 May 2019 and 26 June 2019
average of 2 written lecture tests %

4. PERIODIC TABLE OF ELEMENTS

5. Structures of some organic compounds
Octane number = 100

6. Structures of some organic compounds
Vanilla flower
Vanilla pods

7. Structures of some organic compounds
Antimalarial activity
Cinchona tree

8. Structures of some organic compounds
Fragrance component
Jasmine flowers

9. Structures of some organic compounds
Flavour and cooling effect
Mentha species

10. Structures of some organic compounds
Sugar beet
Sugar cane

11. Structures of some organic compounds
Artificial sweetener

12. Structures of some organic compounds
Synthetic compound increasing man’s sexual potency

13. The main components of organic chemistry as a discipline are these:
1. STRUCTURE DETERMINATION – how to find out the structures
of new compounds even if they are available only in invisibly small
amounts
2. THEORETICAL ORGANIC CHEMISTRY – how to understand those
structures in terms of atoms and the electrons that bind them together
3. REACTIONS MECHANISMS – how to find out how these molecules
react with each other and how to predict their reactions
4. SYNTHESIS – how to design new molecules and then make them
in the laboratory
5. BIOLOGICAL CHEMISTRY – how to find out what Nature does
and how the structures of biologically active molecules are related to
what they do

14. Lectures
Structure and bonding in organic compounds. Covalent and ionic bonds. Hybridization of carbon (sp3, sp2, sp). Basic conceptions and definitions – acidity, basicity, polarity, polarizability, nucleophilicity, electrophilicity. Structure and molecular properties.
Isomerism of organic compounds: constitutional and stereoisomerism (cis-trans isomers, chirality of carbon, optical rotation, absolute configuration of chiral carbon, racemate, enantiomers, diastereomers, meso compounds). Writing and naming of stereoisomers.
Mechanisms of organic reactions – parameters describing the reaction, energy profiles. General types of organic reactions. Writing balanced reaction equations.
Hydrocarbons: alkanes, cycloalkanes (radical halogenation); alkenes, alkynes (electrophilic addition to multiple bonds); arenes (electrophilic aromatic substitution).

15. Lectures
Methods of isolation and purification of organic compounds (crystallization, distillation, chromatography).
Structure determination by spectroscopic methods: general principles of mass spectrometry (MS), infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), ultraviolet spectroscopy (UV).
Alkyl halides – nucleophilic substitution and elimination (SN1, SN2, E1, E2 mechanisms)
Alcohols, phenols – preparation and chemical reactivity.
Ethers and epoxides - preparation and chemical reactivity.
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).

16. Tutorials
Different manners of writing and drawing structural formulas of organic molecules.
Systematic (IUPAC) and common names of hydrocarbons.
Systematic (IUPAC) and common names of compounds with single functional group.
Isomerism of organic compounds.
a) Constitutional isomerism
b) Stereoisomerism. Writing and drawing stereoisomers on the plane.
Cis-trans isomers of alkenes and cycloalkanes.
Chirality of organic molecules – enantiomers. Absolute and relative configuration of chiral centre.
Equation of chemical reaction – its meaning and application. Material balance in chemical equation.
Classifying of organic reactions into general categories: addition, elimination, substitution, rearrangement.
Chemical reactivity of hydrocarbons: alkanes, alkenes, alkynes, arenes.

17. Textbooks
In English:
John McMurry, “Organic Chemistry”, 8th ed. Brooks/Cole Publishing Co., Pacific Grove, California (or earlier editions)
K. P. C. Vollhardt, N. E. Schore, “Organic Chemistry, Structure and Function”, 3rd ed. W. H. Freeman and Co., New York 1999
F. A. Bettelheim, J. March, “General, Organic and Biochemistry”, 5th ed. Harcourt Brace College Publishers 1998
J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford University Press 2000
In Polish:
John McMurry, “Chemia organiczna”, t1/2, translation from 4th ed., PWN Warszawa 2000 (or later editions)
H. Hart, L. E. Craine, D. J. Hart, “Chemia organiczna. Krótki kurs”, Wyd. I, PZWL Warszawa 1999

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

20. ORGANIC CHEMISTRY 1 Lecture 1 Different manners of writing and drawing
structural formulas of organic molecules
Systematic (IUPAC) and common names of hydrocarbons
Systematic (IUPAC) and common
names of compounds with single functional group.

21. Language of organic
chemists

22. Types of organic compounds
HYDROCARBON FRAMEWORK
HYDROCARBON FRAMEWORK
FUNCTIONAL GROUP

23. Drawing and naming of organic structures

24. Rules for drawing skeletal structures
Carbon atoms are not shown. They assumed to be at each intersection of two lines (bonds) and at the end of each line. Occasionally, a carbon atom might be indicated for emphasis or clarity.
Hydrogen atoms bonded to carbon are not shown. Since carbon has always valence of 4, we mentally supply the correct number of hydrogen atoms to fill the valence of each carbon.
All atoms other than carbon and hydrogen (heteroatoms) are indicated.

25. ALKANES (saturated hydrocarbons, aliphatic hydrocarbons)
Do not contain functional groups

26. Functional groups. With carbon-carbon multiple bonds (aromatic ring)
Alkene Alkyne Arene
(aromatic ring)

27. Types of functional groups.
With carbon singly bonded to an electronegative atom
Alkyl halide Alcohol Ether
Amine Thiol (thioalcohol) Sulfide (thioether)

28. Functional groups. With carbon-oxygen double bond (carbonyl groups)
Aldehyde Ketone Carboxylic acid
Ester Amide Acid chloride

29. Naming alkanes according to IUPAC rules
Prefix—Parent—Suffix
What are substituents? How many carbons? What family?

30. Parent names of chain alkanes from C1 to C20
C1 methane
C2 ethane
C3 propane
C4 butane
C5 pentane
C6 hexane
C7 heptane
C8 octane
C9 nonane
C10 decane
C11 undecane
C12 dodecane
C13 tridecane
C14 tetradecane
C15 pentadecane
C16 hexadecane
C17 heptadecane
C18 octadecane
C19 nonadecane
C20 eicosane

31. Naming alkanes according to IUPAC rules
Step 1. Find the parent hydrocarbon – that means find the longest continuous
carbon chain in the molecule:
If 2 different chains are equal, choose the one with the larger number of branch
points:

32. Naming alkanes according to IUPAC rules
Step 2. Number the atoms in the main chain beginning at the end nearer
the first branch point:
If there is branching an equal distance away from both ends, begin numbering at the end nearer the second branch point:

33. Naming alkanes according to IUPAC rules
Step 3. Identify and number the substituents:
on C3, CH2CH3 (3-ethyl) on C2, CH (2-methyl)
on C4, CH (4-methyl) on C4, CH (4-methyl)
on C7, CH (7-methyl) on C4, CH2CH3 (4-ethyl)
3-ethyl-4,7-dimethylnonane ethyl-2,4-dimethylhexane
Step 4. Write the name as a single word using hyphen to separate different
prefixes, and commas to separate numbers.
Prefixes should appear in alphabetical order.

34. Naming alkanes according to IUPAC rules
Step 5. When a substituent of the main chain has its own sub-branching.
The name of complex substituent is formed applying the steps 1-4 just as
if the substituent was a compound itself. Numbering in complex substituent
starts always at the point of attachment to the main chain.

35. Common names of straight-chain and branched-chain
alkyl substituents derived from C3 – C4 alkanes
propane propyl isopropyl
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butane butyl sec-butyl

36. Common names of straight-chain and branched-chain
alkyl substituents derived from C4 – C5 alkanes
isobutane isobutyl tert-butyl
pentane pentyl

37. Common names of straight-chain and branched-chain
alkyl substituents derived from C5 alkanes
isopentane isopentyl tert-pentyl
neopentane neopentyl

38. Naming cycloalkanes according to IUPAC rules
Step 1. Use the cycloalkane name as the parent name
When alkyl substituent contains more carbons than ring,
use alkane as parent name.

39. Naming cycloalkanes according to IUPAC rules
Step 2. In substituted cycloalkanes number the atoms in the ring starting
at the point of attachment so as to arrive at the lowest sum. When different
substituents are present, they are numbered by alphabetical priority.
correct
wrong

40. Nomenclature of alkenes according to IUPAC rules
Alkenes are named according to a series of rules similar to those developed for alkanes, with the suffix –ene used instead of -ane to identify the family.
Step 1. Find the parent hydrocarbon – that means find the longest carbon chain containing the double bond:
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41. Step 2. Number the atoms in the chain beginning at the end nearer the double
bond. If the double bond is equidistant from the two ends, begin at the end nearer
the first branch point. This rule assures that the double bond carbons receive the
lowest possible numbers:
2-hexene methyl-3-hexene
Step 3. Write the full name numbering the substituents according to their position in the chain and listing them alphabetically. Indicate the position of the double bond by giving the number of the first alkene carbon. If more than one double bond is present indicate the position of each and use the suffixes -diene, -triene, -tetraene, and so on.
2-ethyl-1-pentene methyl-1,3-butadiene

42. Common names of unsaturated substituents
accepted by IUPAC
methylene ethylidene vinyl allyl
ethenyl propenyl

43. Common and systematic names of some alkenes
Systematic name Common name
Ethene Ethylene
Propene Propylene
2-Methylpropene Isobutylene
2-methyl-1,3-butadiene Isoprene

44. Naming cycloalkenes according to IUPAC rules
Cycloalkenes are named in a similar way, but because there is no chain end
to begin from, we number the cycloalkene so that the double bond is
between C1 and C2 and the first substituent has as low number as possible.
1-methylcyclohexene ,4-cyclohexadiene ,5-dimethylcyclopentene

45. Nomenclature of alkynes according to IUPAC rules
Alkynes follow the general rules of hydrocarbon nomenclature.
The suffix –yne is used to denote an alkyne, and the position of the triple bond is indicated by its number in the chain. Numbering always begins at the chain end nearer the triple bond so that the triple bond receives as low a number as possible.
6-methyl-3-octyne

46. 4-methyl-7-nonen-1-yne 1-hepten-6-yne
Compounds with more than one triple bond are called diynes, triynes and so forth; compounds containing both double and triple bonds are called enynes (not ynenes). Numbering of an enyne chain always starts from the end nearer the first multiple bond, whether double or triple. When there is a choice in numbering, though, double bonds receive lower numbers than do triple bonds.
4-methyl-7-nonen-1-yne hepten-6-yne
4-methylnon-7-en-1-yne hept-1-en-6-yne
Names of alkynyl substituents:
ethynyl propynyl butynyl

47. Nomenclature of arenes
Benzene Ethylbenzene Bromobenzene
Disubstituted benzene derivatives:
ortho-dibromobenzene meta-dibromobenzene para-dibromobenzene
o-dibromobenzene m-dibromobenzene p-dibromobenzene
1,2-dibromobenzene ,3-dibromobenzene ,4-dibromobenzene

48. and substituents are listed alphabetically
In tri- and more substituted benzenes the lowest possible numbers are used,
and substituents are listed alphabetically
1,2-dibromo-4-methylbenzene ,3,5-trimethylbenzene ,4-dibromo-2,5-dimethylbenzene

49. Aryl substituents
Phenyl Benzyl
C6H C6H5CH2-
Ph PhCH2- Bn

50. Common names of some alkylbenzenes
p-Cymene o-Xylene m-Xylene p-Xylene
1-isopropyl-4-methylbenzene ,2-dimethylbenzene ,3-dimethylbenzene ,4-dimethylbenzene
Cumene Mesitylene Styrene
Isopropylbenzene ,3,5-trimethylbenzene Vinylbenzene
Ethenylbenzene

51. Some aromatic hydrocarbons found in coal tar
Benzene Toluene ortho-Xylene Indene Naphthalene
Biphenyl Anthracene Fluorene Phenanthrene

52. Every organic compound consists of hydrocarbon framework
(and some contain also functional group)
Type of skeleton and functional group
determine both - physical properties and chemical reactivity of compound.
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53. Reactivity of functional group essentially the same,
Aliphatic aldehyde Aromatic aldehyde
Reactivity of functional group essentially the same,
reactivity of hydrocarbon part different

54. Reactivity of hydrocarbon part essentially the same,
Aliphatic amine Aliphatic carboxylic acid
Reactivity of hydrocarbon part essentially the same,
reactivity of functional group totally different

55. Overview of
functional groups in
organic molecules

56. Families of organic compounds
Family name Functional group structure Example Name ending
-ane
pentane
Alkane
-ene
2-pentene
Alkene
-yne
1-pentyne
Alkyne
None
benzene
Arene

57. None
3-chloropentane
Halide
-ol
2-pentanol
Alcohol
ether
dipentyl ether
Ether

58. -amine
pentylamine
Amine
-nitrile
pentanenitrile
Nitrile
None
3-nitropentane
Nitro

59. -thiol
2-pentanthiol
Thiol
sulfide
dipentyl sulfide
Sulfide
sulfoxide
dipentyl sulfoxide
Sulfoxide
sulfone
dipentyl sulfone
Sulfone

60. -al
pentanal
Aldehyde
-one
2-pentanone
Ketone

61. -oic acid
pentanoic acid
Carboxylic acid
-oate
ethyl pentanoate
Ester

62. Amide
-amide
pentanamide
-amide
N-methylpentanamide
-amide
N,N-dimethylpentanamide

63. -oyl chloride
pentanoyl chloride
Carboxylic acid
chloride
Carboxylic acid
anhydride
-oic anhydride
pentanoic anhydride

64. Naming of compounds
containing single
functional group

65. carbon atom of functional group
In chain structures with functional group
containing carbon, like:
nitrile (-CN),
aldehyde (-CHO),
carboxylic acid (-COOH),
ester (-COOR),
amide (-CONH2),
acid chloride (-COCl)
carbon atom of functional group
has to be number 1

66. When functional group containing carbon, like:
nitrile (-CN), suffix -nitrile
aldehyde (-CHO), suffix -al
carboxylic (-COOH), suffix -oic acid
ester (-COOR), suffix -oate
amide (-CONH2), suffix -amide
acid chloride (-COCl) suffix -oyl chloride
is directly linked to the ring, the suffix in the IUPAC name is changed to:
-carbonitrile,
-carbaldehyde,
-carboxylic acid,
-carboxylate,
-carbonamide,
-carbonyl chloride

67. ring carbon bonded to functional group
and
ring carbon bonded to functional group
is assign as number 1 !!!

68. EXAMPLES 1 1 Propanenitrile Cyclopropanecarbonitrile 1 1
Butanal Cyclobutanecarbaldehyde 1 1
Pentanoic acid Cyclopentanecarboxylic acid

69. EXAMPLES 1 1 Ethyl hexanoate Ethyl cyclohexanecarboxylate 1 1
Heptanamide Cycloheptanecarbonamide 1 1
Octanoyl chloride Cyclooctanecarbonyl chloride

70. EXAMPLES 1,2-Dimethylcyclopropanecarbonitrile
2-Isopropyl-4-nitrocyclobutanecarbaldehyde
2-Methoxy-4-methylcyclooctanecarbonyl chloride

71. When the following functional groups:
sulfonic (-SO3H),
hydroxyl (-OH),
amino (-NH2),
carbonyl (CO),
are linked to non-terminal carbons
The numbering of parent skeleton should be done in such a way as to assure the lowest possible number for the carbon linked to the functional group

72. 5-Methylheptane-3-sulfonic acid 3-Chloro-4-methylbenzenesulfonic acid
EXAMPLES
5-Methylheptane-3-sulfonic acid
3-Chloro-4-methylbenzenesulfonic acid

73. 1-Cyclohexylbutan-2-ol 5-Isopropyl-2-methylphenol
EXAMPLES
1-Cyclohexylbutan-2-ol
5-Isopropyl-2-methylphenol

74. EXAMPLES 7-Methyloct-7-ene-4-amine 7- Methyl-7-octene-4-amine
4-Ethyl-2-methylcyclohexylamine
4-Ethyl-2-methylcyclohexaneamine

75. 2,2,5-trimethylcyclohexanone
EXAMPLES
Hepta-1,6-dien-3-one
2,2,5-trimethylcyclohexanone

76. All principal functional groups
are of higher priority
than C=C or C≡C bonds!!!

77. SUBORDINATE FUNCTIONAL GROUPS – EXCLUSIVELY AS PREFIXES
-F fluoro-
-Cl chloro-
-Br bromo-
-I iodo-
-NO2 nitro-
-R alkyl- (methyl-, ethyl-, cyclopentyl-….etc.)
-OR alkyloxy- or alkoxy (methoxy-, cyclopentyloxy-…etc.)
-Ar aryl- (phenyl-, naphthyl-, anthryl-…etc.)
-OAr aryloxy- or aroxy- (phenoxy-, naphthyloxy-…etc.)

78. PRIORITY ORDER OF PRINCIPAL FUNCTIONAL GROUPS
(from the highest to the lowest priority)
R4N+Cl- quaternary ammonium chloride
R-COOH carboxylic acid
R-SO3H sulfonic acid

79. R-COO- Na+ carboxylate salt
PRIORITY ORDER OF PRINCIPAL FUNCTIONAL GROUPS
R-COO- Na+ carboxylate salt
R-COOR’ ester
R-COCl acid chloride

80. PRIORITY ORDER OF PRINCIPAL FUNCTIONAL GROUPS
R-CONH2 amide
R-CN nitrile
R-CHO aldehyde

81. PRIORITY ORDER OF PRINCIPAL FUNCTIONAL GROUPS
R-CO-R’ ketone
R-OH alcohol
Ar-OH phenol
R-NH2 amine

82. Common names of some functional
benzene derivatives
Phenol Aniline Benzoic acid Benzaldehyde
Phenylamine Benzenecarboxylic acid Benzenecarbaldehyde
Acetophenone Benzonitrile Salicylic acid Nitrobenzene
1-Phenylethanone Benzenecarbonitrile 2-Hydroxybenzenecarboxylic acid