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Functional Groups
Functional Groups
Most
organic chemistry involves substituents often contain O, N, S, or P also called functional groupsthey are the chemically functional part of the molecule, and are the non-hydrocarbon part
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.
Functional Groups
The
Important:
Table 23.1, page 726 - shows some of the major categories, and their functional groups - KNOW THESE. Table 23.2, p. 727 - alkyl groups
Name parent as normal, add the halogen as a substituent (or prefix) - Examples on page 726
Halogen Substituents
Common
namesp.726 The more highly halogenated the compound is, the higher the b.p. (see Table 23.3, page 728) Few halocarbons found in nature but, readily prepared and used halothane (Fig. 23.3, p.727) and also the hydrofluorocarbons
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
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:
UV light
CH4 + Cl2
CH3Cl + HCl
Substitution Reactions
Treating
benzene with a halogen? Examples on Page 729 Halogens on carbon chains are readily displaced by hydroxide ions (OH1-) to make an alcohol + a salt: R-X + OH1- R-OH + X1CH3-Cl + NaOH CH3-OH + Methanol + sodium chloride NaCl
Substitution Reactions
CH3-I + KOH CH3-OH + KI
Iodomethane Methanol
Predict how the solubility of an alcohol varies with the length of its carbon chain.
Name the reactions of alkenes that may be used to introduce functional groups.
Construct the general structure of an ether and describe how ethers are named.
Alcohols
Alcohols
How
Alcohols
Aliphatic
alcohols classified 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 730
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.
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
Examples on page 731
Alcohols Common names: similar to halocarbons, meaning name the alkyl group, then followed by the word alcohol One carbon alcohol = methyl alcohol
Alcohols
More
than one -OH substituents are called glycols (ethylene glycol?) ** Examples on page 731 ** 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
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
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 water in all proportions; more than 4 carbons are usually less soluble, because the longer carbon chain is more nonpolar
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
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; also an important industrial solvent
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!
Addition Reactions
The
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
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 top of page 734 for the formation of ethanol from ethene + water
Addition Reactions
If
a halogen is added in an addition reaction, the result is a halocarbon that is disubstituted - middle p. 734 The addition of bromine is often used as a test for saturation - p.734 Addition of a hydrogen halide? called monosubstituted halocarbon
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)
Addition Reactions
The
hydrogenation of a double bond is a reduction reaction, which in one sense is defined as the gain of H Top- page 735, ethene is reduced to ethane; cyclohexene is reduced to cyclohexane
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 diExamples on page 735
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 Alcohol used for fuel in the future?
Construct the general formula for carboxylic acids and explain how they are named.
Describe an ester.
alcohol has an oxygen bonded to a carbon group and a hydrogen ether has an oxygen bonded to two carbon groups
An
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!)
Aldehydes and Ketones Ketones - the carbon of the carbonyl group is joined to two other carbons (meaning it is never on the end) Structures - bottom of page 737
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
23.4, page 738 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
(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)
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
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 23.6 page 741
The 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
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
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. 742
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 743
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
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
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
of hydrogen is called a dehydrogenation reaction may require strong heating and a catalyst Note equations at the top on page 744
can be oxidized in steps to carbon dioxide (middle p. 744): methane methanol methanal methanoic acid CO2
the
more reduced (more H) a carbon compound, the more energy it can release upon oxidation
can also be oxidized into other products Dr. Al K. Hall Mr. Al D. Hyde Equations middle of page 745 Preparing aldehydes from a primary alcohol is a problem, because they are then easily oxidized to carboxylic acids
test and Fehlings test are commonly used for aldehyde detection Figure 23.19 p. 745
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
Addition Polymers
An
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
Addition Polymers
Polytetrafluoroethene
(PTFE, or teflon DuPont) is very resistant to heat and chemical corrosion found on nonstick cookware; coating on bearings and bushings used in chemical reactors
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
Condensation Polymers
Ex:
polyethylene terephthalate (PET) Dacron ( DuPont), Fortrel ( Wellman), Polyesters: permanent press clothing, tire cords Sheets of polyester called Mylar ( DuPont), used as magnetic tape in tape recorders and computers, as well as balloons Nylon: carpet, fishing line, hosiery
Condensation Polymers
Examples:
aromatic rings form Nomex ( DuPont), which is a poor electrical conductor; makes parts for electrical fixtures; flame resistant clothing for race car drivers; flame resistant building materials Kevlar ( DuPont): strong and flame resistant
50-60 percent
5-10 percent
5-10 percent
5-10 percent 5-10 percent
5-10 percent
Timeline of Plastics
1862 First man-made plastic
Timeline of Plastics
1926 PVC is invented