1. Chapter 11 Introduction to Organic Chemistry: Alkanes
11.1
Organic Compounds
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2. Organic Compounds An organic compound
Is a compound made from carbon atoms.
Has one or more C atoms.
Has many H atoms.
May also contain O, S, N, and halogens.

3. Properties of Organic Compounds
Typical organic compounds
Contain carbon.
Have covalent bonds.
Have low melting points.
Have low boiling points.
Are flammable.
Are soluble in nonpolar solvents.
Are not soluble in water.
Oil (organic) and
water (inorganic)
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4. Organic vs. Inorganic
Propane, C3H8, is an organic compound used as a fuel.
NaCl, salt, is an inorganic compound composed of Na+ and Cl− ions.
Why is propane an
organic compound, but
NaCl is not?
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5. Comparing Organic and Inorganic Compounds
TABLE 11.1
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6. Learning Check Identify each characteristic as most typical of
compounds that are (I) inorganic or (O) organic.
1. Has a high melting point
2. Is not soluble in water
3. Has a formula CH3─CH2─CH3
4. Has a formula MgCl2
5. Burns easily in air
6. Has covalent bonds

7. Solution Identify each characteristic as most typical of
compounds that are (I) inorganic or (O) organic.
I Has a high melting point
O Is not soluble in water
O Has a formula CH3─CH2─CH3
I Has a formula MgCl2
O Burns easily in air
O Has covalent bonds

8. Writing Formulas for Carbon Compounds
In carbon compounds
Carbon has 4 valence electrons and hydrogen has 1. •
• C • H •
To achieve an octet, C forms four bonds.
H H
 
H  C  H H C H
H H CH4 , methane

9. Tetrahedral Structure of Carbon
VSEPR theory predicts that a carbon atom with four single, covalent bonds has a tetrahedral shape.
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10. Organic Compounds with More Carbon Atoms
In organic molecules with more carbon atoms,
Valence electrons are shared.
Covalent bonds form between carbon and carbon atoms.
Covalent bonds form between carbon and hydrogen atoms.
H H H H
• • • •
H  C  C  H H C C H
H H H H
ethane, CH3─CH3

11. Tetrahedral Structure of Carbon
In molecules with two or more carbon atoms, each carbon atom with four single bonds has a tetrahedral shape.
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12. Chapter 11 Introduction to Organic Chemistry: Alkanes
11.2
Alkanes
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13. Names of Alkanes The names of alkanes
Are determined by the IUPAC (International Union of Pure and Applied Chemistry) system.
Use a prefix to indicate the number of carbons in a chain.
End in –ane.

14. IUPAC Names for Alkanes
TABLE 11.2
The names of organic compounds are determined by the IUPAC rules (International Union of Pure and Applied Chemistry). The stem of the name states the number of carbon atoms in the carbon chain of the compounds. The suffix, in this case –ane, indicates the alkane family.
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15. Learning Check A. Give the name of each compound: 1) CH3—CH3
2) CH3—CH2—CH3
3) CH3—CH2—CH2—CH2—CH2—CH3
B. Write the condensed structural formula of
pentane.

16. Solution A. Give the name of each compound: 1) CH3—CH3 ethane
2) CH3—CH2—CH3 propane
3) CH3—CH2—CH2—CH2—CH2—CH3
hexane
B. Write the condensed structural formula of pentane.
CH3—CH2—CH2—CH2—CH3

17. Structural Formulas
Alkanes are written with structural formulas that are
Expanded to show each bond.
Condensed to show each carbon atom and its attached hydrogen atoms.
Expanded Condensed H
H C H CH4 , methane
In methane, CH4 the four valence electrons of carbon are shared with the single electrons of four hydrogen (H) atoms. Each pair of electrons is a single bond, which can be drawn as a line. When a structure is drawn to show each bond, it is called a complete structural formula.

18. Writing Structural Formulas
Carbon atoms in a chain
Maintain tetrahedral shape.
Are connected in a zig-zag pattern.
Are drawn as 2-dimensional.
Can be written in several conformations.

19. Expanded and Condensed Structures
TABLE 11.3
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20. Line-Bond Formulas
Because each C atom has a tetrahedral arrangement, the order of atoms is not a straight line, but a zigzag pattern.
A line-bond formula abbreviates the carbon atoms and shows only the zigzag pattern of bonds from carbon atom to carbon atom.

21. Conformations The groups attached to a C-C single bond
Rotate around the bond,
Give different relative arrangements called conformations.
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22. Conformations of Butane
Rotation of the end CH3- provides different conformations for butane.
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23. Some Structures for Butane
TABLE 11.3
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24. Hexane has Six Carbon Atoms
Is an alkane with 6 carbon atoms in a continuous chain.
Has a “zig-zag” look because each carbon atom is at the center of a tetrahedron.
Is represented by a ball-and-stick model as
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25. Learning Check A. Write the condensed formula for: H H H H H
H C C C C C H
H H H H H
B. What is its molecular formula?
C. What is its name?

26. Solution
A. CH3CH2CH2CH2CH3
B. C5H12
C. pentane

27. Learning Check Write the condensed structural formula for A. ethane
B. heptane

28. Solution Write the condensed structural formula for A. ethane CH3─CH3
B. heptane CH3─CH2─CH2─CH2─CH2─CH2─CH3

29. Cycloalkanes Cycloalkanes Are cyclic alkanes.
Have 2H fewer than the open chain.
Are named by using the prefix cyclo- before the name of the alkane chain with the same number of carbon atoms.

30. Cycloalkanes The structural formulas of cycloalkanes are usually
represented by geometric figures,
Cyclopropane CH2
CH CH2
Cyclobutane CH CH2
CH CH2

31. More Cycloalkanes
Cyclopentane CH2
CH CH2
CH CH2
Cyclohexane
CH2

32. Learning Check Name the following: A. CH3─CH2─CH2─CH3 B.
C. CH3─CH2─CH2─CH2─CH2─CH2─CH2─CH3 D.

33. Solution Name the following: A. CH3─CH2─CH2─CH3 butane B. cyclopropane
C. CH3─CH2─CH2─CH2─CH2─CH2─CH2─CH3 octane D.
cyclohexane

34. Chapter 11 Introduction to Organic Chemistry: Alkanes
11.3
Alkanes with Substituents
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35. Isomers of Butane Isomers Have the same molecular formula.
Have different atom arrangements.
Of butane (C4H10) consist of a straight chain and a branched chain each with 4 carbon atoms.
branch
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36. Alkyl groups Alkyl groups are Alkanes that are missing one H.
Substituents attached to carbon chains.
Named with a –yl ending. H
H C CH3 methyl
H H
H C C CH3 CH2 ethyl

37. Naming Substituents In the IUPAC system,
A carbon branch is named as an alkyl group.
Halogen atoms are named as halo.

38. Naming Substituents IUPAC Common methyl ethyl propyl n-propyl
Isopropyl
butyl
n-butyl
1-methylpropyl
sec-butyl
2-methylpropyl
Isobutyl
1,1-dimethylethyl
tert-butyl or
t-butyl

39. Naming Substituents
IUPAC
Fluoro
Chloro
Bromo
Iodo
Hydroxy

40. Alkanes with Alkyl Groups
CH3
CH3 CH CH methylpropane
methyl groups
CH CH3
CH3 CH CH2 CH CH ,4-dimethylpentane

41. Naming Alkanes with Substituents
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42. Guide to Naming Alkanes
Give the name of CH3 CH3
 
CH3─CH─CH─CH3
STEP Longest chain is butane.
STEP Number chain. CH3 CH3
 
STEP 3 Locate substituents and name.
2,3-dimethylbutane

43. Learning Check
Write the IUPAC name for
Cl CH3
 
CH3─CH2─CH─CH─CH3

44. Solution STEP 1 Longest chain is pentane.
STEP Number chain from end nearest substituent.
Cl CH3 (nearest end)
 
CH3─CH2─CH─CH─CH3
STEP 3 Locate substituents and name alphabetically.
3-chloro-2-methylpentane

45. Learning Check Give the IUPAC name for each of the following:
A CH CH3
| |
CH3─CH─CH2 ─CH─CH2─CH3
B Cl CH3
CH3─CH2─CH─CH2─C─CH2─CH3 | Cl

46. Solution A. CH3 CH3 | | CH3─CH─CH2 ─CH─CH2─CH3 2,4-dimethylhexane
| |
CH3─CH─CH2 ─CH─CH2─CH3 2,4-dimethylhexane
B Cl CH more substituents on C3
CH3─CH2─CH─CH2─C─CH2─CH3 | Cl
3,5-dichloro-3-methylheptane

47. Drawing Alkane Structures
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48. What is In A Name?
The structural formula is drawn from the IUPAC name.
2, 4-dimethylhexane
2, dimethyl hexane
Location of Two CH3- groups carbon main chain
branches on attached with single C-C bonds
main chain

49. Learning Check Draw the condensed structural formula for
2-bromo-4-chlorobutane.

50. Solution STEP 1 Longest chain has 4 carbon atoms. C─C─C─C
STEP Number chain and add substituents. Br 
C ─ C ─ C ─ C ─ Cl
STEP 3 Add hydrogen to complete 4 bonds to each C.
CH3─CH─CH2─CH2─Cl

51. Naming Cycloalkanes with Substituents
The name of a substituent is placed in front of the
cycloalkane name.
CH3
methylcyclobutane
Number ring with two substituents
1-bromo-2-chlorocyclopentane Br Cl

52. Learning Check
Name each of the following:
CH3
CH2─CH3 2. Cl

53. Solution Name each of the following: 1. methylcyclopropane
2. 3-chloro-1-ethylcyclohexane

54. Learning Check
Write three isomers of C5H12 and name each.

55. Solution A chain of 5 carbon atoms CH3─CH2─CH2─CH2─CH3 pentane
A chain of 4 carbon atoms and 1 carbon branch
CH3 │
CH3─CH─CH2─CH methylbutane
A chain of 3 carbon atoms and 2 carbon branches
CH3─CH─CH3 2,2-dimethylpropane

56. Chapter 11 Introduction to Organic Chemistry: Alkanes
11.4
Properties of Alkanes
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57. Some Properties of Alkanes
The properties of alkanes include
being
Nonpolar.
Insoluble in water.
Less dense than water
Flammable in air.
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58. Alkanes with 1-4 Carbon Atoms
Alkanes with 1-4 carbon atoms are
Methane, ethane, propane, and butane.
Gases at room temperature.
Used as heating fuels.
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59. Alkanes with 5-17 Carbon Atoms
Alkanes with 5-8 carbon atoms are
Liquids at room temperature.
Pentane, hexane, heptane, and octane.
Very volatile.
Used to make gasoline.
Alkanes with 9-17 carbon atoms
Are liquids at room temperature
Have higher boiling points.
Are found in kerosene, diesel, and jet fuels.

60. Alkanes with 18 or more Carbon Atoms
Have high molar masses.
Are waxy solids at room temperature.
Used in waxy coatings of fruits and vegetables.
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61. Boiling Points of Pentanes
BPs of alkanes
Are lowest of organic compounds.
Increase with larger molecules due to increased dispersion forces.
Decrease for branched alkanes.
Increase for cycloalkanes.

62. Learning Check For the following pairs of hydrocarbon, which one has
the higher boiling point? Why?
1. butane or octane
2. hexane or 2,3-dimethylbutane

63. Solution For the following pairs of hydrocarbon, which one has
the higher boiling point? Why?
1. butane or octane octane has more carbon atoms
2. hexane or 2,3-dimethylbutane
hexane is not branched

64. Crude Oil The hydrocarbons in crude oil are
Separated by boiling points.
Heated to higher temperatures to produce gases that can be removed and cooled.
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65. Classification of Carbon Atoms
The classification of carbon atoms indicates the
number of carbon atoms attached.
A primary carbon (1°) bonds to one carbon atom.
A secondary carbon (2°) bonds to two carbon atoms.
A tertiary carbon (3°) bonds to three carbon atoms.
CH3 |
CH3 —CH2—CH2—CH3 CH3—CH—CH3
primary secondary tertiary

66. Combustion of Alkanes Alkanes
Undergo combustion by reacting with oxygen to produce carbon dioxide, water, and energy.
Are typically not very reactive due to strong C-C single bonds.
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alkane + O CO2 + H2O + energy

67. Balancing A Combustion Equation
Write the equation
C5H12 + O CO2 + H2O
Balance C
C5H12 + O CO2 + H2O
Balance H
C5H12 + O CO2 + 6H2O
Balance O with O2
C5H12 + 8O CO2 + 6H2O balanced

68. Learning Check Propane is used to provide heat for
cooking or warming a room. Write a
balanced equation for the complete
combustion of propane.
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69. Solution Unbalanced equation C3H8 + O2 CO2 + H2O Balance C
Balance H
C3H8 + O CO2 + 4H2O
Balance O
C3H8 + 5O CO2 + 4H2O (Balanced)
To balance the atoms in the formula C3H8, we place a coefficient of 3 in front of CO2 and a coefficient of 4 in front of H2O. The total O in the products is 10 O (6 O in 3CO2 and 4 O in 4 H2O). To balance the 10 O, a coefficient of 5 is placed in front of the O2.

70. Learning Check
Write a balanced equation for the reaction for the complete combustion of heptane C7H16.

71. Solution C7H16 + O2 CO2 + H2O C7H16 + O2 7CO2 + 8H2O
Balanced equation:
C7H O CO2 + 8H2O

72. Learning Check
Write the combustion reaction for ethane and balance.

73. Solution ethane CH3CH3 = C2H6 C2H6 + O2 2CO2 + 3H2O
Write the combustion reaction for ethane and balance.
ethane CH3CH3 = C2H6
C2H O2 2CO H2O
C2H O2 2CO H2O
C2H /2 O2 2CO H2O
Multiply through by 2 to clear
2C2H O2 4CO H2O balanced

74. Halogenation of Alkanes (Substitution)
When alkanes react with halogens,
The reaction is called substitution, one or more H atoms are replaced with a halogen usually Cl or Br.
Light or heat is required.
A mixture of halogenated products result, but we write the
equation with the monosubstituted product.
Example: ethane and chloride
light
CH3—CH3 + Cl2 CH3—CH2 —Cl

75. Learning Check
Give the structures and names of the possible monosubstituted products for the reaction of propane with bromine in the presence of light.

76. Solution CH3—CH2—CH2— Br 1-bromopropane; propyl bromide Br |
Give the structures and names of the possible monosubstituted products for the reaction of propane with bromine in the presence of light.
CH3—CH2—CH2— Br
1-bromopropane; propyl bromide Br |
CH3—CH—CH3
2-bromopropane; isopropyl bromide

77. Chapter 11 Organic Chemistry
11.5
Functional Groups
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78. Elements in Organic Compounds
In organic molecules,
C atoms form bonds
Mostly with H and other C atoms.
Sometimes atoms of O, N, S, and halogens F, Cl, and Br.

79. Functional Groups Functional groups are
A characteristic feature of organic molecules that behave in a predictable way.
Composed of an atom or group of atoms.
Groups that replace a H in the corresponding alkane.
A way to classify families of organic compounds.

80. Some Functional Groups

81. Alkenes and Alkynes
Alkenes contain a double bond between adjacent carbon atoms.
Alkynes contain a triple bond.
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82. Alcohols and Ethers
An alcohol contains the hydroxyl (-OH) functional group.
In an ether, an oxygen atom is bonded to two carbon atoms
–C–O–C– .
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83. More Functional Groups

84. Aldehydes and Ketones
An aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom, attached to at least one hydrogen.
In a ketone, the carbon of the carbonyl group is attached to two other carbon atoms.
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85. Carboxylic Acids and Esters
Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. O 
— C—OH
An ester contains the carboxyl group between carbon atoms.
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86. Amines and Amides In amines, the functional group is a nitrogen atom.|
—N —
In amides, the hydroxyl group of a carboxylic acid is replaced by a nitrogen group.
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87. Summary of Functional Groups

88. Functional Groups in Everyday Items
Methyl amine (fish)
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89. Learning Check 1) CH3–CH2–CH2–OH 2) CH3–O–CH2–CH3 3) CH3–CH2–NH2 O O
Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine.
1) CH3–CH2–CH2–OH
2) CH3–O–CH2–CH3
3) CH3–CH2–NH2
O O
|| ||
4) CH3–C–OH 5) CH3–C–O–CH3

90. Solution 1) CH3─CH2─CH2─OH 2) CH3─O─CH2─CH3 alcohol ether
Classify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine.
1) CH3─CH2─CH2─OH 2) CH3─O─CH2─CH3
alcohol ether
3) CH3─CH2─NH2 amine
O O
|| ||
4) CH3─C─OH 5) CH3─C─O─CH3
carboxylic acid ester