Petroleum: Breaking and Making Bonds

1
Petroleum Breaking and Making Bonds

• Unit 3

2
Do Now

• READ pp. 210-211
• (Some claims made may not be valid)
• Answer the following questions
• What do you like about the commercial
• What do you not like about the commercial
• What would your commercial look like?

3
Objectives

• 1. SWBAT answer short answer and multiple choice
  questions on 2.D.
• 2. SWBAT identify the objectives and requirements
  for the unit 3 project.
• 3. SWBAT identify petroleum based projects and
  hypothesize what life would be like without
  petroleum.

4
In this unit

• You will learn about
• Molecules that make up petroleum
• Uses as fuels product building blocks
• Learning will help you analyze the claims

5
Unit Project

• Teams will design present advertisements
  featuring an imaginary, but plausible, vehicle
  that uses a particular type of fuel
• Biodiesel
• Compressed natural gas
• Hybrid gasoline-electric
• Hydrogen-oxygen fuel cell
• Other

6
Unit Overview

• A. Petroleum What is It?
• Refining of uses for petroleum
• Electrons covalent bonding in hydr0carbons
• Representations of formula for hydrocarbons
• Intermolecular forces properties of hydrocarbons

7
3A. Petroleum What is It?

• pp. 212-236

8
Do Now P. 1

• What is petroleum?
• What material is it mined from?
• What two elements is petroleum made from?

9
Objectives

• 1. SWBAT describe the chemical makeup of
  petroleum and how its refined.2. SWBAT describe
  and give examples of uses for petroleum.3. SWBAT
  explain hydrocarbon combustion reaction.4. SWBAT
  apply the location of petroleum to business,
  politics, and economy.

10
Intro to 3.A. Petroleum

• Lets make a list of the following items on the
  teachers desk

11
Objectives

• 1. SWBAT describe the chemical makeup of
  petroleum and how its refined.
• 2. SWBAT describe and give examples of uses for
  petroleum.
• 3. SWBAT explain hydrocarbon combustion reaction.
• 4. SWBAT apply the location of petroleum to
  business, politics, and economy.

12
Intro to 3.A. Petroleum

• Lets make a list of the following items on the
  teachers desk

13
3A. Petroleum What is It?

• Script for car ad highlighted energy
  fuel-related features that claimed to help
  conserve petroleum resources
• What properties make petroleum useful for burning
  building?
• Focus on key compounds in petroleum
• Their physical properties, molecular structure,
  how atoms bond to make these key compounds

14
3A.1 What is Petroleum?

• Crude oil petroleum pumped from underground
• Mixture of many compounds
• Colorless to greenish-brown to black
• Fluid as water or as resistant to flow as soft
  tar. Crude oil is not useable
• Must be refined separated into simpler mixtures

15
3A.1 What is Petroleum?

• Some mixtures are ready to use
• Others require more refining
• Refined petroleum is mainly a mixture of
  hydrocarbons, molecular compounds that contain
  only atoms of hydrogen (H) and carbon (C)

16
3A.1 What is Petroleum?

• Most petroleum is used as a fuel (89)
• Burning petroleum provides nearly ½ of the total
  U.S. energy needs
• Gasoline powers millions of U.S. automobiles,
  each traveling 14,000 miles per year
• Other petroleum based fuels heat homes office
  buildings, deliver energy to generate
  electricity, power diesel engines jet aircraft

17
Think Pair - Share

• 1. What percent of petroleum is used for fuel?
• 2. What two elements is petroleum made from?
• 3. List two products that are made from
  petroleum.
• 4. What is petroleum mined from?

18
3A.1 What is Petroleum?

• Petroleum is also a raw material for many
  familiar useful products
• New substances (e.g., medications plastics)
  (7)
• Other products (e.g., lubricants, road-paving
  tar) (4)
• Nonrenewable resource

19
Petroleum Products
20
3A.1 What is Petroleum?

• What happens to the molecules contained in
  petroleum when they are burned or used in
  manufacturing?
• The atoms in them rearrange to form new molecules
  as they do in all chemical reactions

21
3A.1 What is Petroleum?

• When hydrocarbons burn, the react with oxygen in
  the air to produce carbon dioxide and water
  and, of course, energy
• CxHx O2 ? CO2 H2O energy

22
3A.1 What is Petroleum?

• Methane burning
• CH4 2O2 ? CO2 2H2O energy

23
3A.1 What is Petroleum?

• Ethane burning
• C2H6 7O2 ? 4CO2 6H2O energy

24
3A.1 What is Petroleum?

• Petroleum is not uniformly distributed around the
  world
• 66 Middle Eastern Nations
• 5 North America
• 4 Central Asia, Far East, Oceana
• Figure 3.4, p. 214 more details

25
3A.1 What is Petroleum?
26
3A.1 What is Petroleum?
27
Using the diagram on pg. 214

• Answer the questions on worksheet 3.A.1.
• We will discuss answers as a class.

28
Using the diagram on pg. 214

• How would the following might affect the
  long-term regional petroleum availability, use,
  and trade
• 1. Industrialization/modernization of second and
  third world nations
• 2. Political unrest in the Middle East
• 3. Population growth in China and India
• 4. Depilation of Alaskan oil reserves

29
Do Now p. 1

• 1. Which area of the world contains the most
  petroleum?
• 2. What area of the world uses the most
  petroleum?
• 3. What product of burning fossil fuels is a
  danger to our environment?
• 4. What is the goal of the combustion reaction?

30
Objectives

• 1. SWBAT explain fractional distillation.
• 2. SWBAT draw and label a fractional distillation
  tower by temperature, intermolecular forces, and
  number of hydrocarbons.
• 3. SWBAT describe the relationship between
  alkanes and their boiling points.

31
A.2 Separation by Distillation

• pp. 215-218 Investigating Matter

32
Distillation

• Separation of liquid substances based on their
  different boiling points
• Distillate
• Condensed liquid collected

33
Distillation of a Mixture
34
A.3 Petroleum Refining
35
3A.3 Petroleum Refining

• Crude oil is a mixture of many compounds
• It takes more than simple distillation to
  separate them
• Refining process separates the crude oil mixture
  into several smaller mixtures, called fractions
• This process is called fractional distillation
• Compounds in each fraction have a particular
  range of boiling points specific uses

36
Refining Crude Oil

• These fractionating towers contain many different
  levels of condensers to cool the oil vapor as it
  rises. Temperatures range from about 400oC (at
  the base) to 40oC (at the top).

37
3A.3 Petroleum Refining

• Crude oil is heated to about 400oC in a furnace
• Pumped into the base of a distilling column
  (fractionating tower), which is usually more than
  100 ft (30 m) tall
• Many components of the heated crude oil vaporize

38
3A.3 Petroleum Refining

• Temperature of the distilling column is highest
  at the bottom
• Temperature drops towards the top
• Trays arranged at appropriate heights inside the
  column collect the various condensed fractions

39
3A.3 Petroleum Refining

• Smaller, lighter molecules lowest boiling
  points either condense high in the column or
  are drawn off the top of the tower as gases

40
3A.3 Petroleum Refining

• Fractions with larger molecules higher boiling
  points are more difficult to separate
• Require more heat energy to vaporize
• Condense back into a liquid in trays lower in the
  column

41
3A.3 Petroleum Refining

• Substances with the highest boiling points never
  vaporize
• Thick (viscous) liquids, called bottoms, drain
  from the columns base

42
Refer to Figure 3.9, p. 219
43
3A.4 Examining Petroleums Molecules

• pp. 219-220

44
3A.4 Examining Petroleums Molecules

• 1. Petroleums gaseous fraction
• compounds with low boiling points (less than
  40oC)
• small hydrocarbon molecules 1-4 carbons
• Low intermolecular forces (forces of attraction)
• LESS INTERMOLECULAR FORCES Easily separate rise

45
3A.4 Examining Petroleums Molecules

• 2. Petroleums liquid fraction varied
• boiling points (less than 40oC 370oC)
• 5-20 carbons
• higher intermolecular forces

46
3A.4 Examining Petroleums Molecules

• 3. Petroleums greasy fraction viscous bottoms
• boiling points (over 370oC)
• Over 20 carbons
• highest intermolecular forces
• Solids at room temperature

47
Think-Pair-Share

• Draw a fractioning tower
• Label the following
• Gasoline
• Gases
• High temperature/Low temperature
• Viscous substances
• Crude oil
• Heat source
• Short hydrocarbons/ Long hydrocarbons
• Strong intermolecular forces/Weak intermolecular
  forces

48
3A.5 Hydrocarbon Boiling Points

• p. 220, Developing Skills
• LAB!

49
Do Now

• Label the following picture
• Diesel
• Gasoline
• Heat Source
• Residue
• Crude Oil
• Gas

50
Objectives

• 1. SWBAT review fractional distillation.
• 2. SWBAT define covalent bonding.
• 3. SWBAT draw Lewis dot structures for several
  elements.

51
3A.6 Chemical Bonding

• pp. 220-224

52
3A.6 Chemical Bonding

• Organic Chemistry focuses on hydrocarbons
  substances that are made from them
• Called organic, because early chemists that
  living systems were needed to produce
  hydrocarbons
• Not so for 150 years - reactants other than
  petroleum have been used to make organic
  compounds

53
3A.6 Chemical Bonding

• Hydrocarbon molecules
• Carbon atoms join to make a carbon chain backbone
• Hydrogen atoms are attached to the carbon chain
  backbone
• Carbons ability to bond the way it does explains
  the abundance of different hydrocarbon compounds

54
Hydrocarbon Chains
55
3A.6 Chemical Bonding

• What holds atoms together?
• Answer is related to the arrangement of electrons
  in atoms.

56
3A.6 Chemical Bonding

• Atoms
• Nucleus
• Protons
• Neutrons
• Shells (Energy Levels)
• Electrons
• Each shell can hold a specific maximum number of
  electrons

57
3A.6 Chemical Bonding

• Refer to Periodic Table
• H 1e- in 1st shell
• He 2e- in 1st shell
• 1st shell only holds 2e-, so new shell starts

58

• Li 3e- - 2 in 1st shell, 1 in 2nd shell
• Be 4e- - 2 in 1st shell, 2 in 2nd shell
• B 5e- - 2 in 1st shell, 3 in 2nd shell
• C 6e- - 2 in 1st shell, 4 in 2nd shell
• N 7e- - 2 in 1st shell, 5 in 2nd shell
• O 8e- - 2 in 1st shell, 6 in 2nd shell
• F 9e- - 2 in 1st shell, 7 in 2nd shell
• Ne 10e- - 2 in 1st shell, 8 in 2nd shell
• 2nd shell only holds 8e-, so new shell starts

59
3A.6 Chemical Bonding
60
3A.6 Chemical Bonding

• Atoms whose last (outer) shell is filled are
  unreactive
• Found on the right side of the Periodic Table
  Group 18
• They all have 8 e- in the outer shell (except for
  He, because the 1st shell can only hold 2e-)
• Called the noble gases or inert gases

61
3A.6 Chemical Bonding

• Atoms in Group 17 are very reactive
• They tend to gain 1e- to finish the shell
• Example F 1e- ? F1- (8e- in outer shell)
• Atoms in Group 1 are very reactive
• They tend to lose 1e-. In the process, they lose
  the entire outer shell. The shell that is now
  exposed is filled, or finished.
• Example Na ? Na1 1e- (8e- in outer shell)

62
3A.6 Chemical Bonding

• Compounds made of nonmetals achieve filled outer
  shells by sharing electrons
• Covalent bonding
• H has 1e- in a shell that can hold 2e-. So, it
  is missing 1e-
• If two H atoms come together, they can each share
  the 1e- they have. Each H has the use of its e-
  as well as the use of the e- from the other H.

63
3A.6 Chemical Bonding

• H? ?H ?
  HH
• Single covalent bond 1 shared pair of e-

64
3A.6 Chemical Bonding

• C atom has 6e-, 2 in the 1st shell 4 in the 2nd
  
• 2nd shell needs 4 more e- to have a total of 8e-
• Methane, CH4, is the simplest hydrocarbon
• What would the dot equation look like?
• 4 single bonds

65
3A.6 Chemical Bonding

• Structures showing the valence e- as dots are
  called
• Electron-dot formulas
• Lewis dot structures
• Lewis structures

66
3A.6 Chemical Bonding

• For convenience, each e- pair can be written as a
  dash. These kind of representations are called a
  structural formulas.

67
3A.6 Chemical Bonding

• These are all 2-dimensional representations of
  molecules
• 3-dimensional models give a more accurate
  representation
• Help predict a molecules physical chemical
  behavior
• In 3A.7, you will build models of alkanes
• Each carbon in an alkane forms 4 single covalent
  bonds with other atoms

68
Worksheet 2.A.6
69
Do Now

• Draw the Lewis Dot Structure for
• 1. C
• 2. H
• 3. N
• 4. Br

70
Objectives

• 1. SWBAT define covalent bonding.
• 2. SWBAT draw Lewis dot structures for several
  elements.
• 3. SWBAT draw the Lewis dot structure and
  structural formula for several different
  molecules.

71
Drawing Lewis Dot Structures for Molecules

• Rule 1 Add together the number of valence
  electrons for each atom.
• Rule 2 Write out the elements without their
  electrons.
• Rule 3 Add electrons around the elements.
• Rule 4 Check to make sure EACH element has a
  filled valence shell.
• Rule 5 Count the number of electrons around each
  element and compare it to step 1. They should
  have the same number.

72
Lets Try Some Examples

• 1. C2H6

73
A.9. Nomenclature

• DO NOW
• Draw the lewis dot and structural formula for
  propanol.
• C3H7OH

74
Objectives

• 1. SWBAT build and describe ball and stick models
  of isomers.
• 2. SWBAT differentiate among straight carbon,
  branched carbon, and ring structures.
• 3. SWBAT determine the IUPAC name for alkanes and
  draw out molecules.

75
Alkanes, Alkenes, Alkynes,

• Alkanes hydrocarbons with single bonds
• Alkenes hydrocarbons with one or more double
  bonds
• Alkynes carbons with one or more triple bond

76
Vocabulary Terms

• Straight-Chain Alkanes
• Carbons in a straight line
• Branched-Chain Alkanes
• One carbons can be linked to 3 or 4 other carbons
• Ring Structure Alkanes
• Form a circle of carbons

77
Vocabulary Terms (Cont.)

• Structural Isomer
• Molecules that have the same molecular formula
  but different arrangements of atoms.

Structural Isomers of Propanol
78
Prefix Carbon
Meth 1
Eth 2
Prop 3
But 4
Pent 5
Hex 6
Hept 7
Oct 8
Non 9
Dec 10
79
Naming of Alkanes
80
(No Transcript)
81
Practice Problems

• Worksheet Supplement 3.A.9

82
3A.7 Modeling Alkanes

• pp. 224-228, Investigating Matter

83
Do Now-Name the following compounds

• 1. CH3-CH2-CH2-CH2-CH3
• 2. CH3-CH-CH2-CH
• I
• CH3
• 3. 4.

84
Objectives

• 1. SWBAT graph alkanes and determine the best fit
  line through the data.
• 2. SWBAT answer questions analyzing the data
  points.

85
A.7 Modeling Alkanes

• Tetrahedron
• 3D shape similar to a pyramid
• Condensed Formula
• CH3-CH2-CH2-CH3
• Write out all the carbons
• Molecular Formula
• C4H10
• CnH(n2)
• Each type of atom is written only once

86
A.8. Graphing/Homework

• Turn to page 228.
• Graph the data on page 226
• Answer questions 1-3 on page 229

87
Do Now

• What did you notice about the number of carbons
  and boiling points of alkanes?
• Why do you think this happens?

88
Objectives

• 1. SWBAT draw models of isomers.
• 2. SWBAT draw a conclusion about branched vs.
  straight chain isomers and boiling points.
• 3. SWBAT hypothesize about how climate affects
  molecules in different fuels.

89
A.9 Alkanes Revisited

• Drawing structural isomers
• Draw 2 isomers of butane

90
Think-Pair-Share

• Try to come up with an many as possible
  structural isomers for hexane.

91
A.10 Boiling points of Alkane Isomers

• Turn to page 231 and with a partner answer
  questions 1-3

92
What was the purpose of this activity?

• http//www.whfreeman.com/ChemCom/
• The more branches the LOWER the boiling point.
• WHY?
• The more compact, spherical shape of the branched
  isomer affords fewer contacts. (Easier to
  separate).
• Less Surface Area

93
Homework

• Pg. 235 29-31, 33, 34, 37, 38

94
Do Now

• Draw the lewis dot structure and structural
  formula for the following molecules
• 1. CF4
• 2. H2O
• 3. NH3

95
Objectives

• 1. SWBAT answer multiple choice and matching
  questions in a jeopardy game to review for their
  test on Thursday.

96
(No Transcript)
97
(No Transcript)
98
Take out a card

• Using the worksheet, list
• 1. your name
• 2. 2 things your understand
• 3. 2 things you want to review next class.

99
Naming (IUPAC)

• 1.  The yne suffix (ending) indicates an alkyne
  or ene suffix indicates an alkene.
•  2.   Select the longest chain containing the
  double or triple bond.  3.   Number from the end
  nearest the double or triple bond.
• 4. Specify where the bond
• starts.
• EX.

100
Lets try some examples

• 1.
• 2. CH3-CHCH-CH3
• 3. CH3-C CH
• CH3-C C-CH3