1. Organic Chemistry
Introduction
Functional Groups
Alkanes
Alkenes
Alkynes
Alcohols
Acids, Esters and Amides

2. Introduction
Organic chemistry is the study of carbon-containing compounds
The field of organic chemistry is very important for a wide variety of reasons.
A huge number of carbon-containing compounds are known.
Most of the advances in the pharmaceutical industry are based on a knowledge of organic chemistry.
Life as we know it is based on organic chemistry.

3. Introduction
Most organic compounds have a “skeleton” that is composed of C-C bonds.
The C-C bonds may be single bonds, double bonds, or triple bonds.
Carbon forms a total of 4 bonds.
The “skeleton” of an organic compound has H’s attached to it.
other “heteroatoms” like O, halogens, N, S, and P may be present as well

4. Introduction propane methane acetylene acetone
Some familiar organic compounds:
propane
methane
acetylene
acetone

5. Introduction Acetic acid “ether” aspirin Ethyl alcohol
Some familiar organic compounds:
Acetic acid
“ether”
aspirin
Ethyl alcohol

6. Introduction
Organic compounds are commonly classified and named based on the type of functional group present.
An atom or group of atoms that influences the way the molecule functions, reacts or behaves.
The center of reactivity in an organic compound

7. Functional Groups
On your exam, you will be responsible for recognizing and naming the various common functional groups that are found in organic compounds:
Use Table 25.4 and the following slides to help you study

8. Functional Groups Class of Compound Functional Group Alkane None
Cycloalkane
Alkyl halide
Alkene
Alkyne
Alcohol
Ether

9. Functional Groups Class of Compound Functional Group Aldehyde Ketone
Carboxylic Acid
Ester

10. Functional Groups Class of Compound Functional Group Amine Amide
Nitrile
Aromatic ring

11. Alkanes Contain C-C single bonds no functional group
Tetrahedral electron domain geometry
sp3 hybridized carbons
Free rotation around single bonds
propane

12. Cycloalkanes
Contain C – C with at least 3 of the carbons arranged in a cyclic (ring) structure
No functional group
Tetrahedral
sp3 hybrid orbitals

13. Alkyl Halides
Contain C-halogen bond
F, Cl, Br, or I

14. Alkenes Contain C=C (carbon-carbon double bonds)
1 sigma bond & 1 pi bond
Trigonal planar geometry
sp2 hybridized carbons
Which atoms must be coplanar in an alkene?
1-propene

15. Alkenes
The C=C present in an alkene is composed of 1 sigma (s) bond and 1 pi (p) bond.
Double bonds are rigid and cannot rotate freely.
Rotation would cause loss of overlap of the p orbitals, destroying the p bond.
ethylene

16. Alkynes Contain C C triple bonds Linear electron domain geometry
1 sigma bond
2 pi bonds
Linear electron domain geometry
sp hybridized carbons
Which atoms must be co-linear in an alkyne?

17. Aromatic Ring
Planar ring system with alternating single and double bonds
does not react like an alkene
Trigonal planar
sp2 hybridized carbons
Benzene ring is a very common aromatic ring.
benzene
pyridine

18. Functional Groups Alkanes are often called saturated hydrocarbons
Organic compounds composed of carbon and hydrogen that contain the largest possible number of hydrogen atoms per carbon atom.
Alkenes, alkynes, and aromatic hydrocarbons are called unsaturated hydrocarbons
Organic compounds composed of carbon and hydrogen that contain less hydrogen than an alkane having the same number of carbon atoms

19. Alcohols Contain C-O-H bond hydroxyl group
Alcohols form hydrogen bonds.
How does hydrogen bonding affect boiling point???
Amphoteric

20. Ethers Contain C-O-C bond tetrahedral e.d. geometry
bent molecular geo.

21. Amines Contain C-N-R R’ R and R’ can be H or C
Primary and secondary amines form hydrogen bonds.
Common organic bases
lone pair of e- on N
primary
secondary
tertiary

22. Aldehydes Contain (-CHO) Carbonyl (C=O) trigonal planar geometry
always on the 1st or last carbon in a chain
trigonal planar geometry
sp2 hybrid orbitals

23. Ketones Contain Trigonal planar e.d. geo. sp2 hybridized C O C-C-C
Carbonyl attached to middle of chain
Trigonal planar e.d. geo.
sp2 hybridized C

24. Carboxylic Acids Contain carboxyl group Form hydrogen bonds
trigonal planar
sp2 hybridized carbon

25. Esters
Contain
trigonal planar
sp2 hybridized

26. Amides Contain C=O is trigonal planar & sp2 hybridized
where R and R’ = H or C
C=O is trigonal planar & sp2 hybridized

27. Nitriles
Contain
Linear
sp hybridized C

28. Functional Groups thyroxine testosterone
Example: Identify the functional groups present in the following compounds.
thyroxine
testosterone

29. Functional Groups
Example: Identify the functional groups in the following compounds.
Lisinopril
Vanillin

30. Depicting Structures of Organic Compounds
Organic compounds can be depicted using a variety of formulas:
Empirical formula
Molecular formula
Lewis structure
Full structural formula
Three dimensional drawings
Condensed structural formula
Line angle drawings

31. Depicting Structures of Organic Compounds
Ethyl acetate is an organic molecule with:
empirical formula = C2H4O
molecular formula = C4H8O2

32. Depicting Structures of Organic Compounds
Ethyl acetate is an organic molecule with:
Lewis structure:
depicts all covalent bonds using a straight line and shows all nonbonding pairs of electrons
Full structural formula:
a Lewis structure without the nonbonding electrons

33. Depicting Structures of Organic Compounds
Ethyl acetate is an organic molecule with:
3-d drawing:
Condensed structural formula
Line angle drawing

34. Alkanes
Some of the simplest alkanes:
You must know these!!!

35. Alkanes
Some of the simplest alkanes:
You must know these!!!

36. Alkanes
The previous alkanes are also called straight-chain hydrocarbons:
all of the carbon atoms are joined in a continuous chain
Alkanes containing 4 or more carbons can also form branched-chain hydrocarbons (branched hydrocarbons)
some of the carbon atoms form a “branch” or side-chain off of the main chain

37. Alkanes 2-methylbutane 2,2-dimethylpropane
An example of a straight chain hydrocarbon:
C5H12 CH3CH2CH2CH2CH3 pentane
Examples of a branched hydrocarbon:
C5H12 CH3CHCH2CH3 CH3
CH3 CH3CCH3
CH3
2-methylbutane
2,2-dimethylpropane

38. Alkanes
The three structures shown previously for C5H12 are structural isomers:
compounds with the same molecular formula but different bonding arrangements
Structural isomers generally have different properties:
different melting points
different boiling points
often different chemical reactivity

39. Alkanes
Organic compounds can be named either using common names or IUPAC names.
You must be able to name alkanes, alkenes, alkynes, and alcohols with 10 or fewer carbons in the main chain using the IUPAC naming system.

40. Alkanes Base name: hexane Alkane Nomenclature:
Find the longest continuous chain of carbon atoms and use the name of the chain for the base name of the compound:
longest chain may not always be written in a straight line 1 2
CH3 - CH - CH3
CH2 - CH2 - CH2 - CH3
Base name:
hexane 3 4 5 6

41. Alkanes A substituent Alkane Nomenclature:
Number the carbon atoms in the longest chain beginning with the end of the chain closest to a substituent
groups attached to the main chain that have taken the place of a hydrogen atom on the main chain 1
A substituent 2
CH3 - CH - CH3
CH2 - CH2 - CH2 - CH3 3 4 5 6

42. Alkanes Alkane Nomenclature:
Name and give the location of each substituent group
A substituent group that is formed by removing an H atom from an alkane is called an alkyl group:
Name alkyl groups by dropping the “ane” ending of the parent alkane and adding “yl”

43. Alkanes Know these! 2-methylhexane Alkane Nomenclature:
Common alkyl groups (substituents):
CH3 methyl
CH3CH2 ethyl
CH3CH2CH2 propyl
CH3CH2CH2CH2 butyl
Know these! 1 2
CH3 - CH - CH3
CH2 - CH2 - CH2 - CH3 3 4 5 6
2-methylhexane

44. Alkanes Alkane Nomenclature:
Halogen atoms are another common class of substituents.
Name halogen substituents as “halo”:
Cl chloro
Br bromo
I iodo
F fluoro

45. Alkanes Know these. Alkane Nomenclature:
When two or more substituents are present, list them in alphabetical order:
Butyl vs. ethyl vs. methyl vs. propyl
When more than one of the same substituent is present (i.e. two methyl groups), use prefixes to indicate the number:
Di = two
Tri = three
Tetra = four
Penta = five
Know these.

46. Alkanes Example: Name the following compounds: CH3CH2CHCH2CH3 CH3

47. Alkanes Example: Name the following compounds: CH3CH2CHCH3 CH2CH2BrCl

48. Alkanes
You must also be able to write the structure of an alkane when given the IUPAC name.
To do so:
Identify the main chain and draw the carbons in it
Identify the substituents (type and #) and attach them to the appropriate carbon atoms on the main chain.
Add hydrogen atoms to the carbons to make a total of 4 bonds to each carbon

49. Alkanes
Example: Write the condensed structure for the following compounds:
3, 3-dimethylpentane
3-ethyl-2-methylhexane
2-methyl-4-propyloctane
1, 2-dichloro-3-methylheptane

50. Alkenes
Alkenes:
unsaturated hydrocarbons that contain a C=C double bond
Alkene Nomenclature:
Names of alkenes are based on the longest continuous chain of carbon atoms that contains the double bond.

51. Alkenes Alkene Nomenclature
Find the longest continuous carbon chain containing the double bond.
Change the “ane” ending from the corresponding alkane to “ene”
butane butene
propane propene
octane octene

52. Alkenes Alkene Nomenclature
Indicate the location of the double bond using a prefix number
designate the carbon atom that is part of the double bond AND nearest to the end of the chain
Name all other substituents in a manner similar to the alkanes.
Use a prefix to indicate the geometric isomer present, if necessary.

53. Alkenes Alkene Nomenclature
Different geometric isomers are possible for many alkenes.
Compounds that have the same molecular formula and the same groups bonded to each other, but different spatial arrangements of the groups
cis isomer
trans isomer

54. Alkenes Alkene Nomenclature Cis isomer:
two identical groups (on adjacent carbons) on the same side of the C = C double bond
Trans isomer:
two identical groups (on adjacent carbons) on opposite sides of the C = C double bond

55. Alkene
CH3 CH3
C = C
H H
CH3 H
C = C
H CH3
cis-2-butene
trans-2-butene

56. Alkene For an alkene with the general formula A P C = C B Q
cis and trans isomers are possible only if
A = B and
P = Q

57. Alkene Example: Name the following alkenes: CH3CH2 H C = C H H
CH3CHCH2 CH2CH3
CH3

58. Alkenes Example: Draw the structures for the following compounds:
2-chloro-3-methyl-2-butene
trans-3, 4-dimethyl-2-pentene
cis-6-methyl-3-heptene

59. Alkynes Alkynes: unsaturated hydrocarbons that contain a
C C triple bond
Alkyne Nomenclature:
Identify the longest continuous chain containing the triple bond
To find the base name, change the ending of the corresponding alkane from “ane” to “yne”

60. Alkynes Alkyne Nomenclature:
Use a number to designate the position of the triple bond
number from the end of the chain closest to the triple bond
just like with alkenes
Name substituents like you do with alkanes and alkenes

61. Alkynes Example: Name the following compounds: CH3CH2C CCHCH3 CH2CH3
ClCH2CH2C CH

62. Alkynes Example: Draw the following alkynes. 4-chloro-2-pentyne
3-propyl-1-hexyne