1. Chapter 11 Principles and Applications of
Power Point to Accompany
Principles and Applications of
Inorganic, Organic, and Biological
Chemistry
Denniston, Topping, and Caret
4th ed
Chapter 11
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

2. Organic Chemistry-History
Historically - compounds from living systems (plants and animals)
A “vital force”, ie. life was thought to be necessary to make organic chemicals.
In 1828 Wohler synthesized urea from purely inorganic chemicals.
Urea, found in urine, was definitely an organic compound!
urea

3. Modern Organic Chemistry
The Study of Carbon Compounds
(some exceptions: for example carbonates, carbon dioxide, etc.)
Biochemistry is now the field that studies chemicals of life.

4. Examples of Organic Chemicals
Foods
Carbohydrates
Fats
Proteins
Clothing
silk, linen, wool,
cotton, Dacron,
Nylon, Orlon,
etc.
Plastics
Pharmaceuticals
Detergents and Soaps
Pesticides
Gasoline and oils
Water purification

5. 11.1 Why is Carbon Unique? 1. Forms four covalent bonds
2. Bonds covalently to: H, O, N, P, S, and all other nonmetals (except noble gases)
3. Carbon atoms join to form:
a. Chains and b. Rings

6. Why is carbon unique?: 2
4. Carbon can form multiple bonds to itself, oxygen, and nitrogen.

7. Why is Carbon Unique?: 3
4. Many carbon compounds exist in the form of isomers.
Isomers are compounds with the same molecular formula but different structures.
An isomer example: A, B, and C all are C4H10 but have different structures. See the next slide!

8. Why is Carbon Unique?: 3b
Isomer Examples. All C4H8

9. Organic vs Inorganic: Differences
Bonding
Covalent
Ionic
Physical State
(room temp)
Gas/liquid common
Solids common
Melting points
Tend to be low
Tend to be very high
Sol. In water
Tend to be insoluble
Much higher percent soluble
Conductivity
Nonconductors
Conduct in soln. and molten

10. Families of Compounds: Hydrocarbons
Hydrocarbons contain only carbon and hydrogen.
They are nonpolar molecules and consequently are not soluble in water but are soluble in typical nonpolar organic solvents like toluene or pentane.
Hydrocarbons are constructed of chains or rings of carbon atoms with sufficient hydrogens to fulfill carbons need for four bonds.

11. Aliphatics Aromatics Structures Based On: Hydrocarbons
Chains and Benzene ring
nonbenzenoid
rings

12. Alkenes and cycloalkenes Alkynes and cycloalkynes
Hydrocarbons
Aliphatics Aromatics
Alkanes and cycloalkanes
Alkenes and cycloalkenes
Alkynes and cycloalkynes

13. Functional groups
Alkanes are compounds that contain only carbon-carbon and carbon-hydrogen single bonds.
For example:

14. Functional groups-2 alkenes have a carbon-carbon double bond
alkynes have a carbon-carbon triple bond

15. Functional groups-3 alcohols have the general formula:
ROH (R is a carbon group)
ethers have the general formulas:
R-O-R, Ar-O-R, Ar-O-Ar
Ar is also a carbon group but is “aromatic”
phenols have the general formula:
Ar-OH (aromatic only!)

16. Functional groups-4 R1 may be H or any carbon group
aldehydes have the general formula
R1 may be H or any carbon group
ketones have the general formula
neither R1 nor R2 can be H
aldehyde carbonyl
ketone carbonyl

17. Functional groups-5 carboxylic acids have the general formula
acid groups
carboxylic acids have the general formula
R1 may be carbon or H
esters have the general formula
R1 may be carbon or H but R2 cannot be H or it would be an acid!
ester carbonyl

18. Functional groups-6 acid chlorides have the general formula
R1 is usually carbon
anhydrides have the general formula
R1 usually is the same as R2 and neither is H

19. Functional groups-7 amines have one of these general formulas
R groups may be alkyl or aromatic
amides have the general formula
All Rs may be carbon or H
amine nitrogens
amide bond

20. Functional Groups-8 thiols (mercaptans) have the general formula
R1 is any carbon group
disulfides have the general formula
R is any carbon group
Rs may be different

21. Test: Identify the groups 1-9
1 an amine
2 a carboxylic acid
3 an ester
4 an alkene
5 an aldehyde
6 an alcohol
7 a ketone
8 a thiol
9 an anhydride

22. 11.2 Alkanes, CnH2n+2 methane CH4 hexane C6H12
The title shows the general formula for a chain alkane.
The first ten alkanes are:
methane CH4 hexane C6H12
ethane C2H6 heptane C7H16
propane C3H8 octane C8H18
butane C4H10 nonane C9H20
pentane C5H12 decane C10 H22

23. Lewis vs Condensed Formulas
The Lewis dot and condensed formulas for methane.
The Lewis dot and condensed formulas for ethane .

24. Drawing Methane and Ethane
Staggered form of ethane

25. Lewis vs Condensed Formulas-2
Lewis dot vs condensed formulas: propane.
Terminal carbons condense to CH3 with the hydrogens usually to the right of the carbon. Interior carbons condense to CH2 .

26. Lewis vs Condensed Formulas-3
A branch or substituent on a chain may be condensed into the chain usually after the carbon from which it branches.

27. IUPAC Names
The IUPAC (International Union of Pure and Applied Chemistry) is responsible for chemistry names.
Before learning the IUPAC rules for naming alkanes, the names and structures of eight alkyl groups must be learned.
These alkyl groups are historical names accepted by the IUPAC and integrated into modern nomenclature.

28. Alkyl Groups
An alkyl group is an alkane with one hydrogen atom removed. It is named by replacing the ane of the alkane name with -yl.
Methane becomes a methyl group.

29. Alkyl Groups-2
All six hydrogens on ethane are equivalent. Removing one H generates the ethyl group.

30. Alkyl Groups-3 isopropyl n-propyl
Propane: removal of a hydrogen generates two different propyl groups depending on whether an end or center H is removed.
n-propyl
isopropyl

31. Alkyl Groups-4a
n-butane gives two butyl groups depending on whether an end (1o) or interior (2o) H is removed.
n-butyl
sec-butyl

32. isobutyl t-butyl Alkyl Groups-4b
Isobutane gives two butyl groups depending on whether a 10 or 30 H is removed.
1o C
3o C
isobutyl
t-butyl

33. IUPAC Names for Alkanes-1
1. The base or parent name for an alkane is determined by the longest chain of carbon atoms in the formula. Note: the longest chain may bend and twist. It is seldom horizontal!
Any carbon groups not part of the base chain are called branches or substituents.
These carbon groups are also called alkyl groups.

34. IUPAC Names for Alkanes-1a
Rules 1 applied. Find the longest chain in each molecule. (Click for answer.)
A= B=8

35. IUPAC Names for Alkanes-2
2. Number the carbon atoms in the chain starting from the end with the first branch. If both branches are equally from the ends, continue until a point of difference occurs.

36. IUPAC Names for Alkanes-2a
Number the carbon atoms correctly.
Left: first branch is on carbon 3.
Right: first branch is on carbon 3 (From top) not carbon 4 (If from right). 1 2 3 4 5 6 7 8 1 2 3 4 5 6 7
this branch would be on C-4
if you started at correct C-8.

37. IUPAC Names for Alkanes-3
3. Prefix the branches/substituents in alphabetical order before the base/stem name (longest chain). Halogens usually come first.
Indicate the position of the branch on the main chain by prefixing its name with the carbon number to which it is attached. Separate numbers and letters with a hyphen.

38. IUPAC Names for Alkanes-3a
4-ethyl-2-methylhexane

39. IUPAC Names for Alkanes-3b
Hyphenated and number prefixes are not considered when alphabetizing groups.
Name the compound below.
5-sec-butyl-4-isopropylnonane

40. IUPAC Names for Alkanes-4
When a branch/substituent occurs more than once, prefix the name with di, tri, tetra,etc. Then prefix the number to the name with a separate number for each occurance. Separate numbers with commas.
eg. 3,4-dimethyl or 4,4,6-triethyl

41. IUPAC Names for Alkanes-4a
5-ethyl-2,3-dimethylheptane
ethyl>dimethyl

42. Test: IUPAC Names
6-ethyl-6-isobutyl-3,3-dimethyldecane

43. Constitutional/Structural Isomers
Constitutional/Structural Isomers differ in how atoms are connected. The two isomers of butane are shown below. The carbon atoms are connected in different patterns.
butane
Bp –0.4 oC
Mp –139 oC
Isobutane
Bp –12 oC
Mp –145 oC

44. 11.3 Cycloalkanes
Cycloalkanes have two less hydrogens than the corresponding chain alkane.
Hexane=C6H14; cyclohexane=C6H12
To name cycloalkanes, prefix cyclo to the name of the corresponding alkane.
Place substituents in alphabetical order before the base name as for alkanes.
For multiple substituents, use the lowest possible set of numbers. A single substituent requires no number.

45. Cycloalkanes-cont. 1-chloro-3- methyl- cyclohexane
Cyclopropane cyclohexane

46. Cis-trans Isomers in Cycloalkanes
Two groups may be on the same side (cis) of the imagined plane of the cycloring or they may be on the opposite side (trans). The two isomers are referred to geometric or cis-trans isomers. E. g.
cis-1-chloro-3-ethylcyclohexane
trans-1-chloro-3-ethylcyclohexane
cis-1,4-dichlorolcyclohexane
trans-1,4-dichlorocyclohexane

47. 11.4 Conformations of Alkanes
Conformations differ only in rotation about carbon-carbon single bonds. Two conformations of butane are shown below. The first (staggered form) is more stable because it allows hydrogens to be farther apart and thus the atoms are less crowded.
Insert Fig 11.6

48. Two conformations of Cyclohexane
Chair form Boat form
(more stable)
E=equitorial
A=axial

49. 11.5 Reactions of Alkanes All alkanes undergo:
Combustion to carbon dioxide and water
Halogenation to haloalkanes

50. Organic Introduction Saturated Hydrocarbons
The End
Organic Introduction Saturated Hydrocarbons