Chapter 23

Functional Groups

Pre-AP Chemistry Charles Page High School Stephen L. Cotton

Section 23.1 - Introduction to Functional Groups

OBJECTIVES:

Explain how organic compounds are classified.

Section 23.1 - Introduction to Functional Groups

OBJECTIVES:

Identify halocarbons and the IUPAC rules for naming halocarbons.

Section 23.1 - Introduction to Functional Groups

OBJECTIVES:

Describe how halocarbons can be prepared.

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

symbol R is used to represent any carbon chains or rings

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

Halogen Substituents Halocarbons - class of organic

compounds containing covalently bonded fluorine, chlorine, bromine, or iodine General formula: R-X (X = halogen)
Naming?

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

CH3CH2Br + NaOH CH3CH2OH + NaBr

Bromoethane Ethanol

Section 23.2 Alcohols and Ethers

OBJECTIVES:

Identify how alcohols are classified and named.

Section 23.2 Alcohols and Ethers

OBJECTIVES:

Predict how the solubility of an alcohol varies with the length of its carbon chain.

Section 23.2 Alcohols and Ethers

OBJECTIVES:

Name the reactions of alkenes that may be used to introduce functional groups.

Section 23.2 Alcohols and Ethers

OBJECTIVES:

Construct the general structure of an ether and describe how ethers are named.

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? (covalent bonding with

the carbon- not ionic with a metal like bases)

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?

Section 23.3 Carbonyl Compounds

OBJECTIVES:

Identify the structure of a carbonyl group as found in aldehydes and ketones.

Section 23.3 Carbonyl Compounds

OBJECTIVES:

Construct the general formula for carboxylic acids and explain how they are named.

Section 23.3 Carbonyl Compounds

OBJECTIVES:

Describe an ester.

Section 23.3 Carbonyl Compounds

OBJECTIVES:

Explain how dehydrogenation is an oxidation reaction.

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

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!)

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 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

Aldehydes and Ketones

Table

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

Aldehydes and Ketones

Benzaldehyde Cinnamaldehyde Vanillin Methanal

(the common name is: formaldehyde) 40% in water is formalin, a preservative

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)

The 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

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 have pleasant, fruity odors- banana, pineapple, perfumes

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

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

Oxidation- Reduction Reactions

Oxidation

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

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

Oxidation- Reduction Reactions

Loss

of hydrogen is called a dehydrogenation reaction may require strong heating and a catalyst Note equations at the top on page 744

Oxidation- Reduction Reactions

Methane

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

Oxidation- Reduction Reactions

Alcohols

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

Oxidation- Reduction Reactions

Benedicts

test and Fehlings test are commonly used for aldehyde detection Figure 23.19 p. 745

Section 23.4 Polymerization

OBJECTIVES:

Describe how addition polymers are formed.

Section 23.4 Polymerization

OBJECTIVES:

Describe how condensation polymers are formed.

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

Polymers from Monomers

Addition Polymers
An

addition polymer forms when unsaturated monomers react to form a polymer

ethene will form polyethylene, shown on page 747 polyethylene is easy to clean, chemically resistant- milk bottles, plastic wrap, refrigerator dishes

High Density Polyethylene

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

Plastic container code system. CODE MATERIAL

Polyethylene Terephthalate (PET) PERCENT OF TOTAL 20-30 percent

High Density Polyethylene

Polyvinyl Chloride (PVC)

50-60 percent
5-10 percent

Low Density Polyethylene

Polypropylene Polystyrene

5-10 percent
5-10 percent 5-10 percent

All other resins

5-10 percent

What Do the Numbers Mean?

1 -- PETE (Polyethylene terephthalate) PET (or PETE) 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...

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...

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...

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...

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...

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...

What Do the Numbers Mean?

7 -- Other This is usually a mixture of various plastics, like squeeze ketchup bottles, "microwaveable" dishes...

Timeline of Plastics
1862 First man-made plastic

1866 Celluloid makes its debut

1891 Rayon is discovered 1907 Bakelite is invented 1913 Cellophane causes the plastics craze

Timeline of Plastics
1926 PVC is invented

1933 Polyethylene is discovered

1933 Saran makes its debut 1938 Teflon is discovered 1939 Nylon stockings hit market 1957 Here comes velcro