Chapter 26 Functional Groups and Organic Reactions - PowerPoint PPT Presentation

1 / 64
About This Presentation
Title:

Chapter 26 Functional Groups and Organic Reactions

Description:

example on top of page 791. Oxidation- Reduction Reactions ... Methane can be oxidized in steps to carbon dioxide (top page 792) ... Equations top of page 793 ... – PowerPoint PPT presentation

Number of Views:307
Avg rating:3.0/5.0
Slides: 65
Provided by: stephen54
Category:

less

Transcript and Presenter's Notes

Title: Chapter 26 Functional Groups and Organic Reactions


1
Chapter 26Functional Groups and Organic Reactions
  • Charles Page High School
  • Dr. Stephen L. Cotton

2
Section 26.1 - Introduction to Functional Groups
  • OBJECTIVES
  • Define a functional group, and give several
    examples.

3
Section 26.1 - Introduction to Functional Groups
  • OBJECTIVES
  • Describe halocarbons, and the substitution
    reactions they undergo.

4
Functional Groups
  • Most organic chemistry involves substituents
  • often contain O, N, S, or P
  • also called functional groups- they are the
    chemically functional part of the molecule, and
    are the non-hydrocarbon part

5
Functional Groups
  • Functional group - a specific arrangement of
    atoms in an organic compound, that is capable of
    characteristic chemical reactions.
  • What is the best way to classify organic
    compounds? By their functional groups.

6
Functional Groups
  • The symbol R is used to represent any carbon
    chains or rings
  • Important Table 26.1, page 774 -- shows some of
    the major categories, and their functional
    groups
  • Table 26.2, p. 775 - alkyl groups

7
Halogen Substituents
  • Halocarbons - class of organic compounds
    containing covalently bonded fluorine, chlorine,
    bromine, or iodine.
  • Naming? Name parent as normal, add the halogen
    as a substituent (or prefix) - Examples on page
    774

8
Halogen Substituents
  • The more highly halogenated the compound is, the
    higher the b.p. (see Table 26.3, page 775)
  • Few halocarbons found in nature
  • but, readily prepared and used
  • halothane (Fig. 26.3, p.776) and also the
    hydrofluorocarbons

9
Substitution Reactions
  • Organic reactions often much slower than
    inorganic reactions
  • must break strong covalent bond
  • trying to find new catalysts to use
  • Substitution - an atom (or group of atoms)
    replaces another atom or group of atoms

10
Substitution Reactions
  • A halogen (shown as X) can replace a hydrogen
    to make a halocarbon
  • R-H X2 ? R-X HX
  • Sunlight is often a sufficient catalyst
  • CH4 Cl2 ? CH3Cl HCl

UV light
11
Substitution Reactions
  • Treating benzene with a halogen? Page 776
  • Halogens on carbon chains are readily displaced
    by hydroxide ions (OH1-) to make an alcohol a
    salt
  • R-X OH1- ? R-OH X1-

12
Substitution Reactions
  • CH3-I KOH ? CH3-OH KI
  • CH3CH2Br NaOH ? CH3CH2OH NaBr

Iodomethane
Methanol
Bromoethane
Ethanol
13
Section 26.2Alcohols and Ethers
  • OBJECTIVES
  • Describe the structures and naming of alcohols
    and ethers

14
Section 26.2Alcohols and Ethers
  • OBJECTIVES
  • Define an addition reaction, and give several
    examples.

15
Section 26.2Alcohols and Ethers
  • OBJECTIVES
  • Compare the properties of alcohols and ethers.

16
Alcohols
  • Alcohols - a class of organic compounds with an
    -OH group
  • The -OH functional group in alcohols is called a
    hydroxyl group thus R-OH is the formula
  • How is this different from the hydroxide ion?

17
Alcohols
  • Arranged into categories according to the number
    of R groups attached to the carbon with the
    hydroxyl
  • 1 R group primary alcohol
  • 2 R groups secondary alcohol
  • 3 R groups tertiary alcohol
  • Note drawings on page 778

18
Alcohols
  • Both IUPAC and common names
  • For IUPAC
  • drop the -e ending of the parent alkane name add
    ending of -ol, numbering the position of -OH
  • parent is the longest chain that contains the
    carbon with the hydroxyl attached.

19
Alcohols
  • The hydroxyl is given the lowest position number
  • Alcohols containing 2, 3, and 4 of the -OH
    substituents are named diols, triols, and tetrols
    respectively

20
Alcohols
  • Common names
  • similar to halocarbons, meaning name the alkyl
    group followed by the word alcohol
  • One carbon alcohol methyl alcohol

21
Alcohols
  • More than one -OH substituents are called glycols
    (ethylene glycol?)
  • Examples on page 779
  • Phenols - compounds in which a hydroxyl group is
    attached directly to an aromatic ring. Cresol is
    the common name of o, m, and p isomers of
    methylphenol

22
Properties of Alcohols
  • Much like water, alcohols are capable of hydrogen
    bonding between molecules
  • this means they will boil at a higher temp. than
    alkanes and halocarbons with a comparable number
    of atoms

23
Properties of Alcohols
  • Alcohols are derivates of water the -OH comes
    from water, and thus are somewhat soluble
  • Alcohols of up to 4 carbons are soluble in all
    proportions more than 4 carbons are usually less
    soluble, because?

24
Properties of Alcohols
  • Many aliphatic alcohols used in laboratories,
    clinics, and industry
  • Isopropyl alcohol (2-propanol) is rubbing
    alcohol used as antiseptic, and a base for
    perfume, creams, lotions, and other cosmetics
  • Ethylene glycol (1,2-ethanediol) - commonly sold
    as antifreeze

25
Properties of Alcohols
  • Glycerol (1,2,3-propanetriol) - used as a
    moistening agent in cosmetics, foods, and drugs
    also a component of fats and oils
  • Ethyl alcohol (ethanol) used in the intoxicating
    beverages an important industrial solvent

26
Properties of Alcohols
  • Denatured alcohol- means it has been made
    poisonous by the addition of other chemicals,
    often methyl alcohol (methanol, or wood alcohol).
    As little as 10 mL of methanol has been known
    to cause permanent blindness, and 30 ml has
    resulted in death!!!

27
Addition Reactions
  • Carbon-carbon single bond is not easy to break
  • In double bonded alkenes, it is easier to break a
    bond
  • Addition reaction- substance is added at the
    double or triple bond location, after it is broken

28
Addition Reactions
  • Addition of water to an alkene is a hydration
    reaction - usually occurs with heat and an acid
    (such as HCl or H2SO4 acting as a catalyst)
  • Note sample at bottom of page 781 for the
    formation of ethanol from ethene water

29
Addition Reactions
  • If a halogen is added in an addition reaction,
    the result is a halocarbon that is disubstituted
    - top page 782
  • The addition of bromine is often used as a test
    for saturation - p.782
  • Addition of a hydrogen halide?

30
Addition Reactions
  • Addition of hydrogen to produce an alkane is a
    hydrogenation reaction, which usually involves a
    catalyst such as Pt or Pd
  • common application is the manufacture of
    margarine from unsaturated vegetable oils

31
Addition Reactions
  • The hydrogenation of a double bond is a reduction
    reaction, which in one sense is defined as the
    gain of H
  • On page 782, ethene is reduced to ethane
    cyclohexene is reduced to cyclohexane

32
Ethers
  • A class of organic compounds in which oxygen is
    bonded to 2 carbon groups R-O-R is formula
  • Naming? The two R groups are alphabetized, and
    followed by ether
  • Two R groups the same? Use the prefix di-
    Examples on page 783

33
Ethers
  • Diethyl ether is the one commonly called just
    ether
  • was the first reliable general anesthetic
  • dangerous- highly flammable, also causing nausea
  • ethers are fairly soluble in water
  • Note the LINK on page 784

34
Section 26.3Carbonyl Compounds
  • OBJECTIVES
  • Distinguish among the carbonyl groups of
    aldehydes, ketones, carboxylic acids, and esters

35
Section 26.3Carbonyl Compounds
  • OBJECTIVES
  • Describe the reactions of compounds that contain
    the carbonyl functional group

36
Aldehydes and Ketones
  • Review
  • alcohol has an oxygen bonded to a carbon group
    and a hydrogen
  • ether has an oxygen bonded to two carbon groups
  • An oxygen can also be bonded to a single carbon
    by a double bond

37
Aldehydes and Ketones
  • The CO group is called the carbonyl group
  • it is the functional group in both aldehydes and
    ketones
  • Aldehydes - carbonyl group always joined to at
    least one hydrogen (meaning it is always on the
    end!)

38
Aldehydes and Ketones
  • Ketones - the carbon of the carbonyl group is
    joined to two other carbons (meaning it is never
    on the end)
  • Structures - middle of page 785

39
Aldehydes and Ketones
  • Naming?
  • Aldehydes identify longest chain containing the
    carbonyl group, then the -e ending replaced by
    -al, such as methanal, ethanal, etc.
  • ketones longest chain w/carbonyl, then new
    ending of -one number it
  • propanone, 2-pentanone, 3-pentanone

40
Aldehydes and Ketones
  • Table 26.4, page 786 examples
  • Neither can form intermolecular hydrogen bonds,
    thus a much lower b.p. than corresponding
    alcohols
  • wide variety have been isolated from plants and
    animals possible fragrant odor or taste many
    common names

41
Aldehydes and Ketones
  • Benzaldehyde
  • Cinnamaldehyde
  • Vanillin
  • Methanal (common formaldehyde)
  • 40 in water is formalin, a preservative

42
Aldehydes and Ketones
  • Propanone (common acetone) is a good solvent
    miscible with water in all proportions
  • why is it a good substance used in nail-polish
    removers?

43
Carboxylic Acids
  • Also have a carbonyl group (CO), but is also
    attached to a hydroxyl group (-OH) carboxyl
    group
  • general formula R-COOH
  • weak acids (ionize slightly)
  • Named by replacing -e with -oic and followed by
    the word acid
  • methanoic acid ethanoic acid

44
Carboxylic Acids
  • Abundant and widely distributed in nature, many
    having a Greek or Latin word describing their
    origin
  • acetic acid from acetum, meaning vinegar
  • many that were isolated from fats are called
    fatty acids
  • Table 26.6 page 789

45
Esters
  • General formula RCOOR
  • Derivatives of the carboxylic acids, in which the
    -OH from the carboxyl group is replaced by an -OR
    from an alcohol
  • carboxylic acid alcohol ? ester water
  • many esters have pleasant, fruity odors- banana,
    pineapple, perfumes

46
Esters
  • Although polar, they do not form hydrogen bonds
    (reason there is no hydrogen bonded to a highly
    electronegative atom)
  • thus, much lower b.p. than the hydrogen-bonded
    carboxylic acids they came from!

47
Esters
  • Can be prepared from a carboxylic acid and an
    alcohol usually a trace of mineral acid added as
    catalyst (because acids are dehydrating agents)
  • Note equation on bottom p. 790

48
Esters
  • Naming? It has 2 words
  • 1st alkyl attached to single bonded oxygen from
    alcohol
  • 2nd take the acid name, remove the -ic acid, add
    -ate
  • example on top of page 791

49
Oxidation- Reduction Reactions
  • All of the previous classes of organic compounds
    are related by oxidation and reduction
    reactions.
  • What is oxidation-reduction?
  • Oxidation the gain of oxygen, loss of hydrogen,
    or loss of e-1
  • Reduction the loss of oxygen, gain of hydrogen,
    or gain of e-1

50
Oxidation- Reduction Reactions
  • Oxidation and reduction reactions (sometimes
    called redox) are coupled- one does not occur
    without the other
  • The number of O and H attached to C indicates the
    degree of oxidation

51
Oxidation- Reduction Reactions
  • The fewer the of H on a C-C bond, the more
    oxidized the bond.
  • Thus, a triple bond is more oxidized than a
    double bond and a single bond
  • An alkane is oxidized (loss of H) to an alkene,
    and then to an alkyne

52
Oxidation- Reduction Reactions
  • Loss of hydrogen is called a dehydrogenation
    reaction
  • may require strong heating and a catalyst
  • Note equations on page 791

53
Oxidation- Reduction Reactions
  • Methane can be oxidized in steps to carbon
    dioxide (top page 792)
  • methane ? methanol ? methanal ? methanoic acid ?
    CO2
  • the more reduced (more H) a carbon compound, the
    more energy it can release upon oxidation

54
Oxidation- Reduction Reactions
  • Alcohols can also be oxidized into other
    products
  • Dr. Al K. Hall ? Mr. Al D. Hyde
  • Equations top of page 793
  • Preparing aldehydes this way is a problem,
    because they are then easily oxidized to
    carboxylic acids

55
Oxidation- Reduction Reactions
  • Benedicts test and Fehlings test are commonly
    used for aldehyde detection - margin p. 793

56
Section 26.4Polymerization
  • OBJECTIVES
  • Define polymer and monomer

57
Section 26.4Polymerization
  • OBJECTIVES
  • Name and describe the uses of some important
    addition and condensation polymers

58
Addition Polymers
  • Polymers are giant molecules, not small like the
    ones studied earlier in this chapter
  • examples are plastics
  • Polymer- large molecule formed by the covalent
    bonding of smaller molecules called monomers

59
Addition Polymers
  • An addition polymer forms when unsaturated
    monomers react to form a polymer
  • ethene will form polyethylene, shown on page 795
  • polyethylene is easy to clean, chemically
    resistant- milk bottles, plastic wrap,
    refrigerator dishes

60
Addition Polymers
  • Polypropylene is a stiffer polymer, used in
    utensils and containers
  • Polystyrene is formed from styrene
    (phenylethene), and is a poor heat conductor
  • molded coffee cups and picnic coolers, insulates
    homes
  • Polyvinyl chloride (PVC) used for pipes in
    plumbing

61
Addition Polymers
  • Polytetrafluoroethene (PTFE, or Teflon) is very
    resistant to heat and chemical corrosion
  • found on nonstick cookware coating on bearings
    and bushings used in chemical reactors

62
Condensation Polymers
  • Condensation polymers are formed by the
    head-to-tail joining of monomer units
  • usually accompanied by the loss of water from the
    reacting monomers, and forming water as a product

63
Condensation Polymers
  • Ex polyethylene terephthalate (PET)
  • Dacron?, Fortrel?, Polyesters permanent press
    clothing, tire cords
  • Sheets of polyester called Mylar?, used as
    magnetic tape in tape recorders and computers, as
    well as balloons
  • Nylon carpet, fishing line, hosiery

64
Condensation Polymers
  • Examples
  • aromatic rings form Nomex?, which is a poor
    electrical conductor makes parts for electrical
    fixtures flame resistant clothing for race car
    drivers flame resistant building materials
  • Kevlar? strong and flame resistant
Write a Comment
User Comments (0)
About PowerShow.com