Dual Prog Lv1

Topic 8 Organic Chemistry: The

Infinite Variety of Carbon
Compounds
Outline
1. Introduction
2. Hydrocarbons
3. Chlorinated hydrocarbons
4. Compounds containing C, H and other elements
 Introduction to Organic Chemistry
• Chemistry of carbon-containing compounds

• Most of these compounds come from living things

– Not necessarily all the case

• ~30 million chemical compounds known

– 95% are compounds containing carbon
 Why is organic chemistry important?
• Organic compounds are everywhere
and affect our daily life
– All living things contain carbon
– Many things we use are made of organic
compounds
• Organic chemicals make up
– Our clothes – natural and synthetic fibers
– Our medicines - aspirin, Tylenol, etc.
– Our food – carbohydrates, proteins, fat…
– Oils, perfumes, paints, plastics, detergents
– Fuels,
– many more…..
 Why carbon can form so many compounds?
• Able to bond strongly to other carbon atoms to form long chains.
– Very few other atoms can form short chains, let alone long chains
• The long chain can be in branched or, ring form.
• Bonds strongly to other elements
– In particular, H, and O & N (heteroatoms) H H
H H H H H H
C
H
H C C H H C C H C C H
C H C C H H C C C H
H H H H H
H H H
Cyclopropane Cyclobutane Cyclohexane
C3H6 C4H8 C6H12
 Types of organic compounds
• Hydrocarbons: containing carbon and hydrogen
only.
– alkanes
– alkenes
– Alkynes
– Aromatics
• Compounds containing carbon, hydrogen and
other elements, e.g.
– Alcohols, ether, carboxylic acid, aldehydes …….
Dual Prog Lv1
Topic 8 Organic Chemistry: The
Infinite Variety of Carbon
Compounds
Outline
1. Introduction
2. Hydrocarbons
3. Chlorinated hydrocarbons
4. Compounds containing C, H and other elements
 Hydrocarbons
• Made of carbon and hydrogen.
• Type of hydrocarbons
Hydrocarbons

Saturated un-saturated

alkanes alkenes alkynes aromatic

 1) Alkanes
• Saturated hydrocarbons

• Contain only single

bonds

• Each C atom has four

bonds.

• Each C has a tetrahedron

geometry.
Common ways to present a hydrocarbon molecule

structure condensed molecular

name or structural formula structural formula formula

H
methane CH4 CH4
H C H
H

H H H3C CH3 or
C2H6
ethane H C C H H3CCH3 or CH3CH3
H H

H H H
propane H C C C H C3H8
H3CCH2CH3
H H H
Another common way to present organic molecules
Skeletal structure:
the location of carbon atoms,
and hydrogen atoms bonded
to carbon, are not denoted by
the symbols C and H, but are
implicit. Carbon atoms are
implied to exist at each vertex.
Carbon atoms are assumed to
have four covalent bonds to
them, so the number of
hydrogen atoms attached to a
particular carbon atom can be
deduced by subtracting the
number of bonds drawn to
that carbon from four.
 Formula and names of alkanes
• Chemical (or molecular) formula:
CnH2n+2
n = 1, 2, 3, …

• Names: All have a –ane ending. A

prefix is used to indicate the number
of carbons. e.g.
– CH4, methane
– C2H6, ethane
– C8H18, octane
Homologous series: A series of
compounds in which each member differs
from the next by a specific number and kind
of atoms.
 Isomerism
• Isomers
• compounds with same molecular
formula but different structures.
• Differences in structure may give rise
to differences in chemical and
physical properties.

Example: H H H
H H H H
Butane H C C C H
H C C C C H isobutane
H H
H H H H H C H
C4H10
butane H

Boiling Temp: Boiling Temp:

0 degree -12 degree
Slide from Chapter 6:
Molecular Shape and Boiling Point
• Number of possible isomers increases rapidly with
the number of carbons
– C30H62 – >4 billion possible isomers
 Properties of Alkanes

Gas

Liquid

Solid

Small alkanes are gas (1-4C), those of 5-16C are liquid, those of
more than 16C are solids (at room temperature)
 Properties of alkanes
• Solubility:
– Soluble in water?
– Soluble in non-polar organic solvents?

• Less dense than water, so they can float on

water surface.
• They can easily burn to produce heat,
– e.g. propane

CH3CH2CH3 + 5 O2 
 Some applications of alkanes
• Gasoline. A complex mixture of
hydrocarbons that have between
5 to 12 carbons.

• Candle: most candles are made

from paraffin, solid alkanes with
20 to 40 carbons.

• Vaseline (Petroleum jelly):

– a semi-solid mixture of alkanes with
carbon numbers mainly higher than 25).
– Applied as an emollient (柔潤劑) or
protective film
 Cyclic Hydrocarbons
• Compounds in which the carbon chains is in the form of
rings.
• Alkanes can have cyclic structures, in addition to linear
chain structures.
H H
H H H H H H
C
H
H C C H H C C H C C H
C H C C H H C C C H
H H H H H
H H H
Cyclopropane Cyclobutane Cyclohexane
C3H6 C4H8 C6H12

General formula: CnH2n

The structure can be represented by skeletal
structures or geometric figures. e.g.
NAME Cyclopropane Cyclobutane Cyclohexane
Molecular formula C3H6 C4H8 C6H12

Structural formula H H
H H H H H H
C
H
H C C H H C C H C C H
C H C C H H C C C H
H H H H H
H H H

Condensed formula H2
H2 C
H2C CH2 H2C C H2C CH2
C C CH2 H2C CH2
H2 H2 C
H2

Geometric figure
 Unsaturated Hydrocarbons
1) Alkenes: hydrocarbons that contain one or more carbon-to-
carbon double bonds.
– General formula: CnH2n
• Alkenylic carbon has a planar geometry.

• Examples:
 Structural isomers
• Isomers may arises due to linkage of carbons and
the geometry of the double bond. e.g.
 Nomenclature for alkenes
• Parent chain = longest continuous carbon chain that
contains the C=C.

alkane => change –ane to –ene

• Use a number to indicate the location of the carbon-carbon

double bond.

• For geometric isomer, use E/Z (or cis/trans) to indicate

which isomer it is.

trans- cis-
Examples of alkenes
 2) Alkyne
• Alkynes: hydrocarbons that contains one or more carbon-
to-carbon triple bonds.
– General formula:
CnH2n-2
• Alkyne carbon has a linear geometry
• Examples:
 Structural isomers
• Isomers may arises due to linkage of carbons and the
position of the triple bond. e.g.
 Nomenclature, alkynes

• Parent chain = longest

continuous carbon chain
that contains the triple
bond.
alkane =>
change –ane to –yne

• Use a number to indicate

the location of the carbon-
1-octyne
carbon triple bond.
C8H14
 Physical properties of alkenes and alkynes
• The physical properties of alkenes and alkynes are quite
similar to those of the corresponding alkanes.
– Those with 2-4 C are gases at RT.
– Those with 5-18 C are liquids at RT.
– Those with >18 C are solids at RT.
• Are they soluble in water?
Chemical properties of alkenes and alkynes
• Alkenes and alkynes are collectively called
unsaturated hydrocarbons
– hydrogen can be added into these organic molecules, e.g.

CH2=CH2 + H2  CH3-CH3

• Like alkanes, they can burn with oxygen

• They can form polymers (will be discussed later)

 Some use of alkenes and alkynes
• Alkenes
– Ethylene is the most important organic chemical.
– Annual US production: > 20 billion kg
– half is used to produce polyethylene, the most
familiar plastics
– Very important materials for organic synthesis

• Alkynes
– Alkynes are used in oxyacetylene
torches for cutting and welding metals.
– Acetylene is also converted to a variety
of other chemical products.
Chemical synthesis involving ethylene
Global demand for ethylene is expected to increase from 79 million tons in 1997
to 114 million tons in 2005. In 1998, the U.S. consumption of ethylene was
approximately 52 billion pounds.
 3) Aromatic Hydrocarbons
• A special type of cyclic or closed ring unsaturated
hydrocarbon, represented by benzene, C6H6.

• Contain double bonds, but do not show the same reactivity

as other unsaturated hydrocarbons

Delocalized molecular
orbitals in benzene
 Aromatic hydrocarbons
• The special structure of benzene makes it very stable, less
reactive than alkenes and alkynes.

• Benzenes and similar compounds and those containing benzene

rings are called aromatic compounds.

• Some additional examples of aromatic compounds:

Property and uses of Aromatic hydrocarbons
• Benzene
– Less dense than water
– often used as solvent and fuel
– used to make other benzene derivatives
– toxic, can cause leukemia after long exposure

• Naphthalene
– used as an insecticide,
especially as a moth
repellant.
Benzene is less reactive than alkenes and alkynes, but they
do react with certain reagents under certain conditions to
give other benzene derivatives. e.g.

•The reaction is called electrophilic substitution reaction

General mechanism
H
+
H +E E + H+
E

Electrophile is Br+, Electrophile is NO2+ generated from

generated from Br2 + H2SO4 + HNO3
FeBr3
DP Lv1 Topic 8
Organic Chemistry: The Infinite
Variety of Carbon Compounds

Outline
1. Introduction
2. Hydrocarbons
3. Chlorinated hydrocarbons
4. Compounds containing C, H and other elements
 Chlorinated Hydrocarbons
• Hydrocarbons containing chlorine atoms.
• Replacement of H by Cl can give hydrocarbons with identical
carbon skeletons and structures
Examples of replacing H with Cl in a CH4
CH3Cl, methyl chloride, or chloromethane
CH2Cl2, or dichloromethane or methylene chloride
CHCl3, trichloromethane, or chloroform
CCl4, tetrachloromethane, or carbon tetrachloride

Polychlorinated
biphenyls (PCBs)
 Properties of Chlorinated Hydrocarbons
All chlorinated hydrocarbons have similar properties
• Add Cl to hydrocarbons
– Increase reactivity of alkanes

• They dissolve fats, oils, and greases

– Useful for dry cleaning

• Chlorinated compounds can be used as insecticides.

• Most of them are toxic, tend to accumulate in fatty tissues.

Chlorinated hydrocarbons can cause severe liver damage.
Dry cleaning:
Washing with an organic solvent

•In use since the 1940s, it is the most common solvent, the "standard" for
cleaning performance, and most aggressive cleaner.

•Better for oil-based stains than more common water-soluble stains

(coffee, wine, blood, etc).

•It can cause color bleeding/loss, and may destroy special trims, buttons
on some garments.

•Known for leaving a characteristic chemical smell on garments.

 Chlorofluorocarbons (CFCs)
Carbon compounds containing fluorine and chlorine are called CFCs.
e.g. common CFCs:
CFCl3, CFC 11; b. p. = 23 oC
CF2Cl2, CFC 12; b. p. = -29.8 oC
CF2ClCF2Cl, CFC 114, b. p. = 3.8 oC

These CFCs are gases or liquid with low boiling points.

Soluble in water? No.

• ideal as propellants widely used in aerosol cans for

deodorants, hair spray, food products, refrigerants.
• CFCs are very inert, so highly persistent in the
environment
• CFCs are bad for the “good ozone” in the atmosphere
(discussed in more details later)
Aerosol spray
A can or bottle that contains a liquid
under pressure.

When the container's valve is opened,

the liquid is forced out of a small hole
and emerges as an aerosol or mist.

Outside the can, the droplets of

propellant evaporate rapidly, leaving the
payload suspended as very fine particles
or droplets.

Typical liquids dispensed in this way are

insecticides, deodorants and paints.
A refrigerant is a compound used in a heat cycle that
reversibly undergoes a phase change from a gas to a
liquid, which can help to lower the temperature.
• https://www.youtube.com/watch?v=wzqTWv8z
GlM
 • The ideal refrigerant
– Has a boiling point somewhat below the target temp.
– Unreactive, chemically inert
– Safe, non-flammable
– Not toxic.
• CFCs meet the requirement.
– CCl2F2 (CFC12), b,p = −29.8 oC
– ClF2CCClF2 (CFC114), b,p = 3.8 oC
• The lack of reactivity gives them a lifespan that can exceed 100 years, giving
them time to diffuse into the upper stratosphere.
• Once in the stratosphere, the sun's ultraviolet radiation is strong enough to cause
the homolytic cleavage of the C-Cl bond,  depletion of the ozone layer
• By the year 2010 CFCs should be completely eliminated from developing
countries as well.
DP Lv1 Topic 8
Organic Chemistry: The Infinite
Variety of Carbon Compounds

Outline
1. Introduction
2. Hydrocarbons
3. Chlorinated hydrocarbons
4. Compounds containing C, H and other elements
Compounds containing carbon, hydrogen and other
elements
A. Concept of functional group:

Organic compounds = alkyl group + functional group

Alkyl groups
Alkyl group: derived from alkane by removing a H
Examples of alkyl groups:
CH3-, methyl, from CH4 (methane)
CH3CH2-, ethyl, from CH3CH3 (ethane)

For a short cut, alkyl group can be represented by the letter R.

Me-

Et-

n-Pr-

i-Pr-
n-Bu-

s-Bu-

i-Bu-

t-Bu-
 Functional Groups
• A group of atoms joined together as a special unit that cause
it to have specific properties and functions. Usually organic
compounds are classified by their functional groups.
• Examples of functional groups:
alkene, double C-to-C bond, C=C
alkyne, triple C-to-C bond, C C
halide, chlorine substitutes, Cl
halide, fluorine substitutes, F
many others to be learned later

Organic compound can be represented by R+functional

group, e.g.:
CH3Cl R-Cl, halide; CH3CH2H R-H, alkane
CH3CH2CH2CH=CH2  RCH=CH2, alkene
 2˚

1˚ 3˚
 B. Examples of Compounds containing carbon,
hydrogen and other elements
Alcohol Family, ROH
• Contains the OH (hydroxyl) group

• Their names are based on corresponding

alkanes (replace -e in alkane with –ol)

• Examples of alcohols
CH4, methane; CH3OH, methanol
CH3CH3, ethane, CH3CH2OH, ethanol
CH3CH2CH2OH, 1-propanol
 Methanol (methyl alcohol), CH3OH
• The simplest alcohol.

• Also called wood alcohol, once made from wood by destructive

distillation.

• Modern industrial production:

CO + 2 H2  CH3OH

• Useful as a solvent, a chemical intermediate.

• Can be used as a replacement for gasoline in automobiles.

• Can cause blindness and even death (drinking as little as 30 mL)

 Ethanol (ethyl alcohol), CH3CH2OH
• In common usage, it is often referred
to simply as alcohol or spirits.

• Made by fermentation or industrial

process

•Fermentation process: one glucose molecule is converted into two ethanol

molecules and two carbon dioxide molecules:

yeast
C6H12O6 → 2 C2H5OH + 2 CO2

•Industrial process: hydration of ethylene:

CH2=CH2 (g) + H2O(g) → CH3CH2OH(l)

Is there any difference in the property of ethanol produced by the two process? NO
 What is denatured alcohol, can we drink it?
• Pure ethanol and alcoholic beverages are heavily taxed, but
ethanol has many uses that do not involve consumption by
humans.
• To relieve the tax burden on these uses, most jurisdictions
waive the tax when an agent has been added to the ethanol to
render it unfit to drink. These include bittering agents such as
denatonium benzoate and toxins such as methanol and pyridine.
• Products of this kind are called denatured alcohol

Denatonium benzoate
 Ethanol and Health
Small amount may be beneficial.
Large amount can be harmful, although it is not as toxic as methanol.
Acts as a mild depressant (鎮靜劑), slows down physical and mental
activity.
 Alcoholic drinking
Alcoholic drinks contain alcohol from 3 to 60%.
- The amount of alcohol (% by volume) in
alcoholic drinks:
Drinks Amount of alcohol
Beer 3 to 8 %
Wine 8 to 18 %
Spirit 12 to 20 %
Whisky
Brandy 30 to 60 %
Vodka
After we drink alcohol,
=> stomach and intestines
absorb alcohol rapidly,
=> alcohol enters the
bloodstream,
=> alcohol is transported
to different parts.

E.g. heart, brain, muscles

Affects the functions of brain

 Physiological Effects from Alcohol

Alcohol is a depressant (抑制劑).

=> affect senses

=> lose control of speech, movements
and emotions.
Effects of alcohol in blood:
Conc. of alcohol per 100 cm3 blood

lose control of speech, movements and

emotions

– 60 mg more than 2 cans of beer

– 40 mg slow in movements

– 30 mg feel happy, relaxed

Effects of alcohol in blood:
Conc. of alcohol per 100 cm3 blood

feel sleepy and tired, lose

– 100 mg
control

– 60 mg lose control of speech, movements and

emotions
Conc. of alcohol per 100 cm3 blood
completely lose consciousness or
– 500 mg even resulting in death or coma

– 300 – 400 mg begin to lose

consciousness
– 200 mg
lose control of urination and
defecation

– 100 mg
feel sleepy and tired, lose
control
 Effects of alcohol on our health
- Liver removes alcohol from blood.

- Drinking too much alcohol at one time,

=> liver cannot remove alcohol completely.
=> alcohol damages the brain.
=> causes loss of memory and
emotional problems.

- Dead brain cells cannot function again.

 Effects of alcohol on our health
- If liver has to remove alcohol for long,

=> it may lead to liver cancer!

- Alcohol stimulates
the mucus lining of
stomach,

=> causing bleeding and stomach ulcer!

Legal limit in HK:

50 mg of alcohol per
100 cm3 blood
or
22 g of alcohol per
100 cm3 breath

Commit the ‘drunk driving’

offence if the above limit is
exceeded.
- The above limit will be exceeded if you
take the following within ONE hour:

> 2 cans of beer (about 600 cm3 )

> 2 glasses of wine (about 250 cm3 )
> 2 pints of whisky (about 50 cm3 )
 Isopropanol
• Isopropyl alcohol also known as rubbing
alcohol.
• Applications:
– used widely as a solvent and as a cleaning fluid
– commonly used in the home as an antiseptic
for cuts and scrapes.

• Toxicity:
– not nearly as toxic as methanol.
– about twice as toxic as ethanol, and acts as a
depressant.
– Around 15 g of isopropanol can have a toxic
effect on a 70 kg human if left untreated.
 Multifunctional Alcohols
• Several common alcohols have more than one –OH groups.

• Ethylene glycol: HOCH2CH2OH

– a main ingredient in antifreeze

• Glycerol: HOCH2CH(OH)CH2OH
– used in lotions to keep skin soft and as food additive to
keep cake moist.
 What is an antifreeze?
• Antifreeze is a substance added to a
solvent, such as water, to lower its
freezing point.

• Antifreeze is typically added to water

in the cooling system of an internal-
combustion engine so that it can be
cooled below the freezing point of
pure water (0 oC) without freezing.

• Ethylene glycol is the most widely

used automotive cooling-system
antifreeze. The term engine coolant is
widely used in the automotive
industry .
 Phenol, PhOH
• One of the H in benzene is replaced by
OH group.
benzene
• Different chemical properties than
other alcohols
• Behaves more like an acid

• Applications:
• Antiseptics
• Disinfectant for floors and furniture

• Toxicity: causes skin irritation OH

Phenol
 Ethers, ROR, or ROR’
• Two alkyl groups attached to same O.
• Example: CH3CH2-O-CH2CH3 or Et2O

• CH3OCH2CH2CH3 methyl propyl ether,

• often used as a solvent

• Properties:
• Little chemical reactivity
• Insoluble in water
• Highly flammable
 Applications of ethers
• As a solvent, e.g.
• CH3CH2-O-CH2CH3, diethyl ether
• As anesthetic (麻醉劑) agents, e.g.
– Neothyl: methyl propyl ether, CH3OCH2CH2CH3
– Penthrane: methoxyflurane, CHCl2CF2OCH3.

• Other use of ethers

• Methyl tert-butyl ether,
CH3OC(CH3)3
• It was added to gasoline as an
antiknock agent and to reduce
emission of CO in automotive
exhaust gas (a pollutant). Methyl tert-butyl ether
How to make ethers? nucleophilic
substitution
 Aldehydes and Ketones
• Both contain a carbonyl group (C=O)
• Aldehyde: R-CHO
• Ketone: R-CO-R’
O O O
C R C H R C R'

C(=O) R C(=O) H R C(=O) R,

or or or
CO RCHO RCOR
a carbonyl group an aldehyde a ketone
 Common Aldehydes
O O O
C C C
H H H CH3 H

formaldehyde acetaldehyde benzaldehyde

• Formaldehyde – used as a preservative for

biological specimens

• Larger ones are used as fragrances

– Benzaldehyde – flavor in maraschino
cherries, found in apricot, cherry and
peach seeds.
 Common Ketones
O O
H3C C CH3 H3C C CH2CH3

acetone ethyl methyl ketone

• Acetone – most common ketone

– Used primarily as a solvent for
such substances as fats, rubbers,
plastics, and varnishes

Nail polish remover

Quick drying varnish
 How to make ketones or aldehydes?
One common ways is through oxidation of alcohols

• Oxygen from
oxidizing agent
H H [O]
R C O R C O + H 2O
R' R'

• If either (or both) of these is hydrogen

you will get an aldehyde
• If both R and R’ are alkyl groups you
will get a ketone
 Examples
H OH H K2Cr2O7 / H2SO4 H O H
H C C C H H C C C H
heat H H
H H H

H OH CrO3 / pyridine H O
H C C H H C C H
CH2Cl2
H H H

Can one convert ketones or aldehydes to alcohols?

 O
- Examples
R' C R O OH
+ ?
C H C H
X-

benzaldehyde H

O-
R' C R
X

NaBH4: Sodium borohydride

 Carboxylic Acids
O O

C OH R C OH
-COOH RCOOH
a carboxyl group a carboxylic acid

Contains a COOH (C=O and –OH group on the same

carbon) group (carboxyl group)
 Names of carboxylic acids
Systematic names of carboxylic acids
• Replace the -e in the alkane name with -oic acid.
CH4 methane HCOOH methanoic acid
CH3—CH3 ethane CH3—COOH ethanoic acid

The common names of simple carboxylic acids

• Are formic acid (1C), acetic acid (2C), propionic acid (3C), and
butyric acid (4C).
HCOOH formic acid
CH3—COOH acetic acid
CH3CH2—COOH propionic acid
CH3CH2CH2—COOH butyric acid
 Common carboxylic acids
O O
O
H3C C OH CH3CH2CH2 C OH
H C OH
HCOOH CH3CH2CH2COOH

formic acid butyric acid or

acetic acid butanoic

Formic acid: first obtained by destructive distillation of

ants, present in stings of ants and bees.

Acetic acid: vinegar, 4-10% acetic acid solution.

Carboxylic acids generally have unpleasant odor!

Butyric acid can be isolated from butter fat.
 Properties of carboxylic acids
• Are weak acids.
• Ionize in water to produce carboxylate ions and hydronium
ions.
O O
║ ║
CH3−C−OH + H2O CH3−C−O– + H3O+

Reacts with base to give “carboxylic acid salts”. e.g.

CH3—COOH + NaOH CH3—COO– Na+ + H2O

acetic acid sodium acetate
(carboxylic acid salt)
 Esters
Esterification:
O H+ O
R'
R C OH + HO R' R C O + H2O

an acid an alcohol an ester

• Derived from carboxylic acids and alcohols.

• Can be made from the reactions of carboxylic acids and alcohol

• General formula: RCOOR’, or RCOOR

 Naming Esters

CH3CH2CH2COOCH3, methyl butyrate

 Properties of esters
• Esters tend to be fragrant (芳香), with fruity
odors and tastes.

– Methyl butyrate  apple

– Ethyl butyrate  pineapple

• Esters are widely used as flavorings (調味品)

in cakes, candies, and other foods and drinks
and as ingredients in perfumes.
Structures and flavors of some esters
 Reactions of Esters
• The carbonyl carbon is electron deficient, thus can be
attacked by nucleophiles.

O O
O _ _
+ C + Nu R C Nu C + OR'
R Nu
R OR'
OR'
 Reactions of Esters
An ester can be hydrolyzed by :
• either an aqueous base
• or an aqueous acid
to yield a carboxylic acid plus an alcohol

O O H - o r H + (c a ta ly tic a m o u n t) O
C + H 2O C + H O R '
R O R' R O H

this type of reaction is called acidic hydrolysis or

basic hydrolysis
 Mechanism of Ester Hydrolysis

Basic hydrolysis
via an addition
intermediate

Acidic Hydrolysis:
reverse of the
esterification
 Reactions of Esters
Ammonia reacts with esters to form amides
Ester Products
Aspirin
• Is used to relieve pain and reduce O
C OH
inflammation.
O
• Is an ester of salicylic acid and
O C CH3
acetic acid.
• Pain reliever: analgesic
O
Methyl salicylate C O CH3

• From Oil of wintergreen (冬青樹)

OH
• Is used to soothe sore muscles.
• Is an ester of salicylic acid and
methanol.
 Nitrogen-containing organic compounds
Amines.
• Derived from ammonia by replacing H with alkyl or
aromatic groups.
• They are bases.
• May have 1, 2, or 3 alkyl or aromatic groups
• Most biological amines are a-amino acids
– Building blocks of proteins

CH3CH2NH2,
ethylamine
CH3NHCH3,
dimethylamine aniline An amino acid
 Amides

In short form: RCONH2, RCONHR’, RCONR’R”

• N bonded directly to carbonyl group

• Linkage that holds proteins together
• Nylon, silk, and wool molecules contain
hundreds of amide functional groups.
Naming of amide: Their names are based on corresponding
alkanes (replace -e in alkane with -amide)
CH3CONH2: acetamide or ethanamide
CH3CH2CH2CONH2: propanamide
 Amides are commonly formed from the reaction
of a carboxylic acid with an amine.
O O
H R
R' OH
+ N X R' N
R + H2O
H H

O
O
H R
N R + HCl
R' Cl
+ R' N
H
H
 Heterocyclic Compounds
• Ring compounds that have elements other than C in
the ring
• Occur in plants
– Alkaloids: basic in solution
– Examples: caffeine, morphine, cocaine
• Form basic structure of DNA
 Heterocyclic Compounds
CH3
N N O

N
N CH3
H3C O
coffee beans
HO

O H
CH3
H N

HO
Poppy plant morphine