chapter 26 functional groups and organic reactions charles page high school dr. stephen l. cotton
TRANSCRIPT
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Chapter 26“Functional Groups and
Organic Reactions”
Charles Page High School
Dr. Stephen L. Cotton
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Section 26.1 - Introduction to Functional Groups
OBJECTIVES:
–Define a functional group, and give several examples.
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Section 26.1 - Introduction to Functional Groups
OBJECTIVES:
–Describe halocarbons, and the substitution reactions they undergo.
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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
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Functional GroupsFunctional 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.
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Functional GroupsThe 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 - KNOW THESE.
Table 26.2, p. 775 - alkyl groups
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Halogen SubstituentsHalocarbons - class of organic
compounds containing covalently bonded fluorine, chlorine, bromine, or iodine–General formula: R-X
Naming? Name parent as normal, add the halogen as a substituent (or prefix) - Examples on page 774
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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
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Substitution ReactionsOrganic 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
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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 + HClUV light
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Substitution ReactionsTreating benzene with a halogen?
Page 776Halogens on carbon chains are
readily displaced by hydroxide ions (OH1-) to make an alcohol + a salt:
R-X + OH1- R-OH + X1-
CH3-Cl + NaOH CH3-OH + NaCl
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Substitution Reactions
CH3-I + KOH CH3-OH + KI
CH3CH2Br + NaOH CH3CH2OH + NaBr
Iodomethane Methanol
Bromoethane Ethanol
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Section 26.2Alcohols and Ethers
OBJECTIVES:
–Describe the structures and naming of alcohols and ethers.
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Section 26.2Alcohols and Ethers
OBJECTIVES:
–Define an addition reaction, and give several examples.
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Section 26.2Alcohols and Ethers
OBJECTIVES:
–Compare the properties of alcohols and ethers.
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AlcoholsAlcohols - 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? (covalent bonding with the carbon- not ionic with a metal like bases)
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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
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Alcohols Both IUPAC and common names For IUPAC:
–drop the -e ending of the parent alkane name; add ending of -ol, number the position of -OH
–parent is the longest chain that contains the carbon with the hydroxyl attached.
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AlcoholsThe hydroxyl is given the
lowest position numberAlcohols containing 2, 3, and 4
of the -OH substituents are named diols, triols, and tetrols respectively–Examples on page 779
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AlcoholsCommon names:
–similar to halocarbons, meaning name the alkyl group followed by the word alcohol
–One carbon alcohol = methyl alcohol
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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
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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
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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…?
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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
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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
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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!!!
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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
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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
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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? -called monosubstituted halocarbon
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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 (making them solid from a liquid)
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Addition Reactions
The hydrogenation of a double bond is a reduction reaction, which in one sense is defined as
the gain of H Bottom- page 782, ethene is
“reduced” to ethane; cyclohexene is “reduced” to cyclohexane
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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
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Ethers Diethyl ether is the one commonly
called just “ether”
–was the first reliable general anesthetic
–dangerous- highly flammable, also causes nausea
ethers are fairly soluble in water Note the LINK on page 784
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Section 26.3Carbonyl Compounds
OBJECTIVES:
–Distinguish among the carbonyl groups of aldehydes, ketones, carboxylic acids, and esters.
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Section 26.3Carbonyl Compounds
OBJECTIVES:
–Describe the reactions of compounds that contain the carbonyl functional group.
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Aldehydes and KetonesReview:
–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
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Aldehydes and Ketones The C=O 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!)
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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
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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
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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
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Aldehydes and Ketones
Benzaldehyde Cinnamaldehyde Vanillin Methanal (common: formaldehyde)
–40% in water is formalin, a preservative
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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? (a powerful solvent-able to dissolve both polar & nonpolar)
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Carboxylic Acids Also have a carbonyl group (C=O),
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
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Carboxylic Acids Abundant and widely distributed in
nature, many having a Greek or Latin word describing their origin
–acetic acid (ethanoic acid) from acetum, meaning vinegar
–many that were isolated from fats are called fatty acids
Table 26.6 page 789
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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
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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
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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
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EstersNaming? 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
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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
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Oxidation- Reduction ReactionsOxidation and reduction
reactions (sometimes called redox) are coupled- one does not occur without the other
The number of Oxygen and Hydrogen attached to Carbon indicates the degree of oxidation
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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
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Oxidation- Reduction Reactions
Loss of hydrogen is called a dehydrogenation reaction
–may require strong heating and a catalyst
Note equations on page 791
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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
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Oxidation- Reduction ReactionsAlcohols can also be oxidized
into other products “Dr. Al K. Hall Mr. Al D. Hyde”Equations top of page 793Preparing aldehydes from a
primaryf alcohol is a problem, because they are then easily oxidized to carboxylic acids
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Oxidation- Reduction Reactions
Benedict’s test and Fehling’s test are commonly used for aldehyde detection - margin p. 793
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Section 26.4Polymerization
OBJECTIVES:
–Define polymer and monomer.
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Section 26.4Polymerization
OBJECTIVES:
–Name and describe the uses of some important addition and condensation polymers.
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Addition PolymersPolymers 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
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Polymers from Monomers
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Addition PolymersAn 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
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High Density Polyethylene
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Addition Polymers Polypropylene is a stiffer polymer, used
in utensils and containers Polystyrene is formed from styrene
(phenylethene), and is a poor heat conductor (styrofoam – Dow Chemical)
–molded coffee cups and picnic coolers, insulates homes
Polyvinyl chloride (PVC) used for pipes in plumbing
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Addition PolymersPolytetrafluoroethene (PTFE, or
“Teflon”) is very resistant to heat and chemical corrosion
–found on nonstick cookware; coating on bearings and bushings used in chemical reactors
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Condensation PolymersCondensation 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
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Condensation Polymers Ex: polyethylene terephthalate (PETE)
–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
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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
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Plastic container code system.
CODE MATERIALPERCENT OF
TOTAL
Polyethylene Terephthalate
(PETE)20-30 percent
High Density Polyethylene 50-60 percent
Polyvinyl Chloride (PVC) 5-10 percent
Low Density Polyethylene 5-10 percent
Polypropylene 5-10 percent
Polystyrene 5-10 percent
All other resins 5-10 percent
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What Do the Numbers Mean?1 -- PETE (Polyethylene terephthalate)
•PET is used in the production of soft drink bottles, peanut butter jars... •PET can be recycled into fiberfill for sleeping bags, carpet fibers, rope, pillows...
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What Do the Numbers Mean?2 -- HDPE (High-density polyethylene)
•HDPE is found in milk jugs, butter tubs, detergent bottles, motor oil bottles... •HDPE can be recycled into flower pots, trash cans, traffic barrier cones, detergent bottles...
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What Do the Numbers Mean?
3 -- V (Polyvinyl chloride)•PVC is used in shampoo bottles, cooking oil bottles, fast food service items... •PVC can be recycled into drainage and irrigation pipes...
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What Do the Numbers Mean?
4 -- LDPE (Low-density polyethylene)
•LDPE is found in grocery bags, bread bags, shrink wrap, margarine tub tops... •LDPE can be recycled into new grocery bags...
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What Do the Numbers Mean?
5 -- PP (Polypropylene)•PP is used in most yogurt containers, straws, pancake syrup bottles, bottle caps.... •PP can be recycled into plastic lumber, car battery cases, manhole steps...
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What Do the Numbers Mean?
6 -- PS (Polystyrene)•PS is found in disposable hot cups, packaging materials (peanuts), and meat trays... •PS can be recycled into plastic lumber, cassette tape boxes, flower pots...
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What Do the Numbers Mean?
7 -- Other•This is usually a mixture of various plastics, like squeeze ketchup bottles, "microwaveable" dishes...
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Timeline of Plastics1862 – First man-made plastic
1866 – Celluloid makes it’s debut
1891 – Rayon is discovered
1907 – Bakelite is invented
1913 – Cellophane causes the plastics craze
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Timeline of Plastics1926 – PVC is invented
1933 – Polyethylene is discovered
1933 – Saran makes it’s debut
1938 – Teflon is discovered
1939 – Nylon stockings hit market
1957 – Here comes velcro