Title: Chapter 26 Functional Groups and Organic Reactions
1Chapter 26Functional Groups and Organic Reactions
- Charles Page High School
- Dr. Stephen L. Cotton
2Section 26.1 - Introduction to Functional Groups
- OBJECTIVES
- Define a functional group, and give several
examples.
3Section 26.1 - Introduction to Functional Groups
- OBJECTIVES
- Describe halocarbons, and the substitution
reactions they undergo.
4Functional 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
5Functional 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.
6Functional 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
7Halogen 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
8Halogen 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
9Substitution 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
10Substitution 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
11Substitution 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-
12Substitution Reactions
- CH3-I KOH ? CH3-OH KI
- CH3CH2Br NaOH ? CH3CH2OH NaBr
Iodomethane
Methanol
Bromoethane
Ethanol
13Section 26.2Alcohols and Ethers
- OBJECTIVES
- Describe the structures and naming of alcohols
and ethers
14Section 26.2Alcohols and Ethers
- OBJECTIVES
- Define an addition reaction, and give several
examples.
15Section 26.2Alcohols and Ethers
- OBJECTIVES
- Compare the properties of alcohols and ethers.
16Alcohols
- 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?
17Alcohols
- 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
18Alcohols
- 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.
19Alcohols
- 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
20Alcohols
- Common names
- similar to halocarbons, meaning name the alkyl
group followed by the word alcohol
- One carbon alcohol methyl alcohol
21Alcohols
- 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
22Properties 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
23Properties 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?
24Properties 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
25Properties 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
26Properties 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!!!
27Addition 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
28Addition 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
29Addition 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?
30Addition 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
31Addition 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
32Ethers
- 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
33Ethers
- 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
34Section 26.3Carbonyl Compounds
- OBJECTIVES
- Distinguish among the carbonyl groups of
aldehydes, ketones, carboxylic acids, and esters
35Section 26.3Carbonyl Compounds
- OBJECTIVES
- Describe the reactions of compounds that contain
the carbonyl functional group
36Aldehydes 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
37Aldehydes 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!)
38Aldehydes 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
39Aldehydes 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
40Aldehydes 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
41Aldehydes and Ketones
- Benzaldehyde
- Cinnamaldehyde
- Vanillin
- Methanal (common formaldehyde)
- 40 in water is formalin, a preservative
42Aldehydes 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?
43Carboxylic 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
44Carboxylic 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
45Esters
- 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
46Esters
- 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!
47Esters
- 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
48Esters
- 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
49Oxidation- 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
50Oxidation- 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
51Oxidation- 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
52Oxidation- Reduction Reactions
- Loss of hydrogen is called a dehydrogenation
reaction
- may require strong heating and a catalyst
- Note equations on page 791
53Oxidation- 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
54Oxidation- 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
55Oxidation- Reduction Reactions
- Benedicts test and Fehlings test are commonly
used for aldehyde detection - margin p. 793
56Section 26.4Polymerization
- OBJECTIVES
- Define polymer and monomer
57Section 26.4Polymerization
- OBJECTIVES
- Name and describe the uses of some important
addition and condensation polymers
58Addition 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
59Addition 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
60Addition 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
61Addition 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
62Condensation 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
63Condensation 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
64Condensation 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