ORGANIC

CHEMISTRY LECTURE TRANSES 1

MIDTERMS ANTROPINE (found in the

stems of tomato plants)
Importance of Organic Chemistry
Organic Chemistry holds a central Advancements in Organic Chemistry
place in chemical studies because its 18th Century
fundamental principles and its § CARL WILLIAM SCHEELE
applications touch virtually all other o Isolated acidic components
disciplines from grapes and lemons by
forming precipitates with
Brief History of Organic Chemistry Ca** or Pb then adding
§ Organic Chemistry became a mineral acids --- TARTARIC
defined science in the 19th century. ACID … CITRIC ACID;
Scheele also isolated uric
Plants have been used for years as acid from urine
folk medicine remidies in Africa, § FRIEDRICH SERTURNER
China, India, and South America. o Isolated a compound from
§ Bark of Cinchona Trees – chewed opium extracts ---
for years to treat symtoms of MORPHINE
malaria § [1820] PIERRE PELLETIER &
QUININE JOSEPH CAVENTOU
§ Ancient Egyptians roasted ox liver o isolated an alkaloid
in the belief that it improved night STRYCHNINE
vision § JUSTUS LEIBIG
VITAMIN A o perfected the science of
§ An ancient atipyretic involved oranic analysis based on
chewing willow bark Lavoisier’s early work
SALICILIN (a derivative of § [1807] JONS J. von BERZELIUS
salicylic acid) o described the substances
obtained from living
Mid 17th Century organisms as organic
§ A new compound was synthesized compounds and that they
called acetylsalicylic acid were only composed of only
ASPIRIN C&H
§ Fermentation of grains and fruits
ETHANOL Early 19th Century JONS JACOB
§ In ancient Bengal, Java and BERZELIUS developed what was known
Guatemala, plants provided a deep as VITAL FORCE THEORY
blue substance used to color
clothing The Vital Force Theory stated that
INDIGO organic compounds could not be made in
§ Ancient Phoenicians used an the lab, but needed a mysterious, God-
extract from a snail to color cloth given power that was found only in living
TYRIAN PURPLE organisms
§ Plant Belladona has been used for
centuries as a poison

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The Vital Force Theory began to decline o introduced the idea of closed
in 1828, when the German chemist valence bonds benzene
Friedrich Wöhler synthesized urea from
inorganic starting materials
§ [1916] GILBERT LEWIS
𝐴𝑔𝑂𝐶𝑁 + 𝑁𝐻4𝐶𝑙 → 𝐴𝑔𝐶𝑙 + 𝑁𝐻4𝑂𝐶𝑁 o introduced the concept of
bond formation due to
𝐴𝑔𝑂𝐶𝑁 : Silver Cyanate sharing of electrons covalent
𝑁𝐻4𝐶𝑙 : Ammonium Chloride bonds
𝐴𝑔𝐶𝑙 : Silver Chloride
𝑁𝐻4𝑂𝐶𝑁 : Ammonium Cyanate

𝐴𝑔𝑂𝐶𝑁 + 𝑁𝐻4𝐶𝑙 → 𝑁𝐻2𝐶𝑂𝑁𝐻2

Life involves Organic Molecules
𝑁𝐻2𝐶𝑂𝑁𝐻2 : Urea ü DNA
ü PROTEINS
§ MARCELLIN BERTHELOT ü NEUROTRANSMITTERS
o Showed that all classes of ü BODY ODOR
organic compounds could be ü FEMALE AND MALE SEX
synthesized HORMONES
o Strongly opposed LOUIS ü BIOLOGICAL FLUIDS
PASTEUR who supported the ü MEDICINES.. DRUGS
vital force theory
(fermentation) ORGANIC INORGANIC
low melting points high melting points
Mid 19th Century low boiling points high boiling points
§ HERMANN KOLBE low solubility in soluble in water
o Prepared ethane via water
electrolysis of potassium highly flammable nonflammable
acetate nonconductive conductive
§ SIR EDWARD FRANKLAND covalent onds ionic bonds
o Prepared butane from
iodoethane and zinc THE CARBON ATOM: BONDING & SHAPE
§ [1849] CHARLES WURTZ A. Covalent Bonding
o discovered amines 1. Carbon
§ ALEXANDER WILLIAMSON 2. Nitrogen
o showed how ethers could be 3. Oxygen, Sulfur
prepared from K salt of an 4. Hydrogen
alcohol and alkyl iodide 5. Halogen Cl, Br, I, F
§ [1863] WILLIAM PERKIN
o prepared the first The required number of valence electrons
commercially synthetic dye of an atom does not have to be achieved
mauve using only single covalent bonds
§ [1859] AUGUST KEKULE

 ORGANIC CHEMISTRY LECTURE TRANSES 3

B. Electron dot formula and Lewis

Structure b. Shape of a molecule with a carbon-
carbon double bond. The
Valence Shell Electron Pair Repulsion hydrogens and carbon form the
Theory (VSEPR) vertices of a triangle. The bond
→ States that electron pairs repel angles are 120°
each other because they have
like charges

Tetrahedral structure of carbon:

a. a regular tetrahedron
b. a carbon atom with tetrahedral
bonds
c. a carbon atom within a regular
tetrahedron
d. a methane molecule, CH4
In a triple bond, the carbon has only two
regions for shared electrons. To be
placed as far apart as possible, a linear-
arrangement is required.

Causes of Organic Compounds

• Alkanes
• Alkenes
• Alkynes
• Aromatic Hydrocarbons
• Alcohols, Phenols, Ethers, Thiols
• Aldehydes and Ketones
• Carboxylic Acids
o Carbohydrates
o Lipids
o Proteins
a. Lewis Structure for C2H4
o Nucleic Acid
• Esters

NOMENCLATURE:
Branched-Chain Alkane

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1. .. according to the Greek prefix
corresponding to the number of
carbon atoms followed by the suffix
–ane. (The name should be based
on the longest chain – parent
chain_
2. Name the attached shorter chains
(alkyl groups)
CH3- methyl
CH3CH2- ethyl
CH3CH2CH2- propyl
CH3(CH2)2CH2- butyl
CH3(CH2)3CH2- pentyl
3. To locate the positions of the alkyl
groups, number the longest carbon Isomers are molecules with the same
chain consecutively from one end molecular formula but different structural
to the other, starting at the end formula.
that will give the lowest number to
the first substituent. Note: There must be the same
number of carbon and hydrogen atoms
but there also must be a completely
different arrangement of Carbon Atoms

CYCLOALKANES

Since cycloalkanes consists of rings of –

CH2- units, they have the General
Formula: (CH2)n, or C2H2n, and are
represented by polygons in skeletal
drawings.

Step (1): Count the number of carbon

atoms in the ring, and add the prefix

 ORGANIC CHEMISTRY LECTURE TRANSES 5

“cyclo” to the name of the PROPERTIES OF SATURATED

corresponding alkane. HYDROCARBONS

Step (2): If a substituent is present on A. Physical State

the ring, the compound is named as an ∗ Both melting and boiling
alkyl-substituted cycloalkane rather points of hydrocarbons
than as a cycloalkyl-substituted alkane. increase with increasing
molecular weight.
Step (3): For substituted ∗ Low molecular weight
cycloalkanes, start at a point of alkanes, including
attachment and number the cycloalkanes, up to about 4
substituents on the ring so as to carbons, are gases at room
arrive at the lowest number. If two or temperature.
more different substituents are present, ∗ Alkanes from 5 to 17
number them by alphabetical carbons, are lipids.
priority. ∗ Larger alkanes are white,
waxy solids like solid
Step (4): If two or more different paraffin.
substituents are present, number them ∗ In any state, alkenes are
by alphabetical priority. colorless, odorless, and
tasteless organic compounds.

B. Solubility. Alkanes are nonpolar

compounds. Therefore they are not
soluble in water; which dissolves
only ions and polar compounds.

C. Density. Each liquid alkane has a

slightly different density, but all are
less dense than water.

CHEMICAL PROPERTIES
∗ The most important chemical
property of alkanes is that they
“burn” – a property called
“combustion”
∗ “complete combustion” gives
only two products:
Carbon Dioxide and Water

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∗ “incomplete combustion” may ∗ Liquid alkanes can cause damage if
yield: they get into the lungs. They
Carbon Monoxide dissole the lipid molecules in the
∗ The chief chemical property of cell membranes and cause
alkanes (including cycloalkanes) is pneumonia-like symptoms. For this
that they are “chemically inert” reason, anyone who swallows liquid
alkanes should not be induced to
SOURCES OF ALKANES vomit them up because some
A. Natural Gas – is formed by the might be forced into the lungs in
anaerobic decay of plants and that manner.
animals (putrefaction). Its main ∗ Liquid alkanes can also harm the
component is Methane (80- skin by similar physical process.
95%), the balance being varying The human skin is kept moist by
amounts of other hydrocarbons. natural body oils. Liquid alkanes
B. Petroleum (crude oil) – is a thick dissolve these oils and cause the
(viscous) black liquid found skin to dry out. However, mixtures
underground consisting of a of high-molecular-weight liquid
mixture of hundreds to thousands alkanes, sold in drugstores under
of different alkanes with varying the name “mineral oil”, soften
amounts of sulfur-, ocygen-, and and moisten skin, like Petroleum
nitrogen- containing organic jelly a mixture of solid and liquid
compounds. hydrocarbons also used to protect
a. Gasoline skin.
b. Kerosene
c. Fuel Oil and Diesel Fuel AROMATIC HYDROCARBONS
d. Lubricating Oil
e. Residue (used for greases, INTRODUCTION
tars, and asphalt)
Source: coal tar
Fragrant odor

Examples: vanilla, cinnamon, cloves,

wintergreen, and roses

wintergreen
BIOLOGICAL EFFECTS OF ALKANES
∗ Because they are so unreactive,
alkanes in general are not
particulary poisonous.
cinnamaldehyde


THE BENZENE STRUCTURE
August Kekule
• Principal founder of the theory of
chemical structure
• Suggested that the structure
contained a 6-membered ring of
atoms with alternating single and
double bonds
The Ourosboros Dream
• KEKULE spoke of the creation of
the theory on how he discovered
the ring shape of benzene molecule
after having a daydream of a snake
seizing its own tail
• This is an ancient symbol known as
OUROBOROS. The vision he said,
came to him after years of
studying the nature
carbon=carbon bonds.
• He also dreamed of a vision of
dancing atoms and molecules that
led to the theory of his structure.
BENZENE
• Benzene and all substances with
structures and chemical properties
that resemble benzene are
classified as aromatic compounds
ORGANIC CHEMISTRY LECTURE TRANSES 7
Representations of Benzene
• Benzene is a cyclic compound
commonly written as a hexagon
with alternating double and single
bonds or with a circle drawn in the
center of a hexagon.
UNUSUAL CHARACTERISTICS OF
BENZENE
• Unexpected Stability: does not
undergo addition reactions wherein
a double bond/s is/are converted
to single bonds; required a catalyst
of (FeBr3); undergoes substitution
rather than addiction
• Carbon-carbon bond length:
physical measurements show that
all C to C lengths in benzene are
identical
single bonds= 1.54 angstrom
double bonds = 1.40 angstrom
triple bonds= 1.34 angstrom
• Bonding in Benzene. The
electrons are not attached to
particular carbon atoms, but are
delocalized and associated with the
entire molecule.
This electronic structure imparts
unusual stability to benzene and is
responsible for many of the
characteristic properties of
aromatic compounds.
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atoms of benzene by another atom
or group of atoms.
• Monosubstituted benzene has the
formula C6H5G, where G is the
group replacing a hydrogen atom.

Monosubstituted Benzenes
• Some monosubstituted benzenes
are named by adding the name of
the substituent group as a prefix to
the word benzene.

CH2CH3 Br
sp2-sp2 orbital overlap to form the carbon
ring structure.
O2N Cl

nitrobenzene ethylbenzene chlorobenzene bromobenzene

• Certain monosubstituted benzenes

have special names.
CH=CH2 OH

CH3

H2N
styrene phenol aniline
O O
2
carbon-hydrogen bonds formed by sp -s C C toluene
OH H
orbital overlap and overlapping p
orbitals.
benzoic acid benzaldehyde

Phenyl Group
• The C6H5- group is known as the
phenyl group, and the name phenyl
is used to name compounds that
cannot easily be named as benzene
pi electron clouds above and below the derivatives.
plane of the carbon ring.
1 CH3
NAMING AROMATIC COMPOUNDS 2 H2
CH 3 4 5 C
CHCH2CH3
Naming Substituted Benzene
Compounds Cl

• A substituted benzene is derived by 3-chloro-2-phenylpentane diphenylmethane

replacing one or more hydrogen

 ORGANIC CHEMISTRY LECTURE TRANSES 9

Disubstituted Benzenes
• The prefixes ortho-, meta-, and
para- (abbreviated o-, m-, and p-)
are used to name disubstituted
benzenes.

Dimethyl Benzenes
• Dimethylbenzene - special name
xylene.
CH3 CH3 CH3

H3C

H3C
ortho-xylene meta-xylene
G CH3
para-xylene
ortho ortho
Polysubstituted Benzenes
• When there are more than two
substituents on a benzene ring, the
meta meta carbon atoms in the ring are
numbered starting at one of the
substituted groups.
para • Numbering must be done in the

direction that gives the lowest
possible numbers to the
substituent groups.

CH3 OH

O2N 1 NO2 1 Cl
6 2 6 2

5 3 5 3
Br
• When one of the substituents 4 4
corresponds to a monosubstituted NO2 5-bromo-2-chlorophenol
benzene that has a special name, 2,4,6-trinitrotoluene (TNT)
the disubstituted compound is
named as a derivative of that Priority of Function Group in
parent compound. Nomenclature

CLASS SUFFIX NAME

Carboxylic acid -oic acid

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ester -oate such as iron (III) chloride or iron (III)
amide -amide bromide, a Cl or Br atom replaces an H
nitrile -nitrile atom to form the products.
aldehyde -al
ketone -one Nitration of Benzene
alcohol -ol
NO2
amine -amine
H2SO4
alkene -ene + HO-NO2 + H2O
alkyne -yne nitric
acid
alkane -ane
benzene nitrobenzene
ether
When benzene reacts with a mixture of
Physical Properties of Aromatic
concentrated nitric acid and concentrated
Hydrocarbons
sulfuric acid at about 50°C, nitrobenzene
is formed.
Substitution Reactions of Aromatic
Hydrocarbons
Alkylation of Benzene
• Halogenation
• Friedel-Crafts Reaction
• Nitration
• Alkylation CH2CH3
• Sulfonation
+ CH3CH2Cl AlCl 3 + HCl
net addition of -Br or -Cl chloro-
net addition of –NO2 ethane
benzene ethylbenzene
net addition of –R (alkyl group)
net addition of SO3H

Halogenation of Benzene
Side-Chain Oxidation
• Carbon chains attached to an
X
FeX3
aromatic ring are fairly easy to
+ X2 + HX oxidize.
bromine or
chlorine CH2CH3 COOH
benzene
bromobenzene or K2Cr2O7/H2SO4
chlorobenzene + CO2
heat

When benzene reacts with chlorine or benzoic acid

ethylbenzene
bromine in the presence of a catalyst

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Sulfonation • Undergo photodecomposition when

• a reversible reaction that produces exposed to UV light from solar
benzenesulfonic acid by adding radiation
sulfur trioxide and fuming sulfuric • In the atmosphere, PAHs can react
acid. with pollutants such as ozone,
• the reaction is reversed by adding nitrogen oxides and sulfur dioxide
hot aqueous acid to producing diones, nitro and dinitro
benzenesulfonic acid to produce PAHs, and sulfonic acids
benzene • Can be degraded by some
microorganisms in the soil

Polycyclic Aromatic Hydrocarbons

Sources
• Crude oil processing
Coal → Coke + Coal gas + Coal tar
• Combustion of natural gas
• Cooking
• Tobacco smoking
• Natural process – carbonization

- Result of pyrolytic processes

Especially the incomplete
combustion of organic materials
during industrial and human
activities such as
- processing of coal and crude oil,
- combustion of natural gas including
vehicular exhaust traffic
- Cooking especially grilling and
charring meat and other food
products

The aromatic hydrocarbons, such as

benzene, toluene, xylene, naphthalene,
POLYCYCLIC AROMATIC
and anthracene, were first obtained in
COMPOUNDS
significant quantities from coal tar.
Large group of organic compounds with 2
or more fused aromatic rings. Aka
FUSED RING AROMATICS
• Relatively low solubility in water
• Highly lipophilic
• Low vapor pressure in air –
adsorbed on particlulate matter

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→ Metal pipe foundries; Cigarette
smoke
o Average total BaP content
in the mainstream of
smoke of cigarette was 35
ng before 1960; 18 ng in
naphthalene phenanthrene
1978-79; modern “low
tar” cigarettes deliver 10
ng BaP. The concentration
of BaP in a room
extremely polluted with
anthracene cigarette smoke was 22
ng/m3

• Drinking water
→ BaP, fluoranthene
→ Not exceeding 0.1µg/litre

• Food
→ Depends on the mode of
cooking, preservation and
storage

• Soil
Routes of Exposure
→ Forest soil range – 5-100µg/kg
• Air
→ Carcinogenic pahs are found in
→ Benzopyrene (BaP)
all surface soils
o a study was conducted in
→ Substantial amounts of PAHs
New Jersey which involved
are transferred to forest soild
a metal pipe foundry
from vegetative litter because
suspected as a major
the compounds are adsorbed
source of BaP = 0.9
from air on organic matter such
ng/m3. the range of BaP
as leaves and needles.
per gram of food was
between 0.004 – 1.2
SIGNIFICANCE
ng/g. drinking water
8 carcinogenic PAHs in the environment:
appeared to be a minor
BENZO(A)ANTHRACENE, CHRYSENE,
pathway of BaP exposures
BENZO(B)FLUORANTHENE,
in the study area. Among
BENZO(K)FLUORANTHENE, BaP, INDENO
the study subjects the
PYRENE, DIBENZOANTRHACENE AND
range and magnitude of
BENZOPERYLENE – this is in north
dietary exposures (2-500
America
ng/day) were much larger
than for nhalation (10-50
ng/day)

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• A ketone functional group may be

Health Effects of BaP located anywhere within a chain or
• Toxicogenic ring and its position is given by a
→ Adverse haematological effects number.
→ Reproductive: Stillbirths, • Chain numbering normally starts at
malformations, tumors the end nearest to the carbonyl
→ Toxicological – aplastic anemia, group.
pancytopenia, severed reduction
in peripheral blood leukocytes,
severe bone marrow depression
• Genotoxic
• Mutagenic
• Carcinogenic
→ Liver, lungs, pituitary &
mammary gland tumors IUPAC NAME: butanal
→ Skin carcinoma Common Name: butyraldehyde

ALDEHYDES AND KETONES

Aldehydes & Ketones

• Aldehydes and Ketones are organic
compounds which incorporate a
carbonyl functional group C=O.
The carbon atom of this group has
two remaining bonds that may be IUPAC Name: 3-hydroxybutanal
occupied by H or an alkyl or an aryl Common Name: 𝛽 − ℎ𝑦𝑑𝑟𝑜𝑥𝑦𝑏𝑢𝑡𝑦𝑟𝑎𝑙𝑑𝑒ℎ𝑦𝑑𝑒
substituent. or aldol
• If at least one of the substituents is
hydrogen H, the compound is an
aldehyde.
• If neither is hydrogen, the
compund is a ketone.

Nomenclature
• The IUPAC system or nomenclature
assigns a characteristic suffix to
the classes.
o –al to aldehydes
o –one to ketones
• Since an aldehyde carbonyl group
IUPAC Name:
must always be at the end of a
p-nitrobenzenecarbaldehyde
carbon chain, it is by default
Common Name: p-nitrobenzaldehyde
position #1. This defines the
numbering direction.

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Sources
• Widespread in nature both in
plants and animals

carvone (spearmint & caravay)

cinnamaldehyde (cinammon bark)

vanillin (vanilla bean) camphor (camphor tree)

rustone (musk dear)

citral (lemongrass)

testosterone (male sex hormone)

helminthosporal (a fungal toxin)

progesterone (female sex hormone)

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cortisone (adrenal hormone) Common Name: formaldehyde

IUPAC Name: methanal
Properties
• Generally, aldehydes and ketones
have higher boiling points than
similar sized alkenes
• The presence of oxygen with its
non-bonding electron pairs
increases their water solubility Common Name: acetaldehyde
relative to hydrocarbons. IUPAC Name: ethanal
• Unlike alcohols, aldehydes and
ketones cannot hydrogen-bond to
themselves, because no hydrogen
atom is attached to the oxygen
atom of the carbonyl group.
• Aldehydes and ketones, therefore,
have lower boiling points than
alcohols of comparable molar
mass.
Common Name: benzaldehyde
Boiling Points of Selected Aldehydes and
Ketones and Corresponding Alcohols

Name Molar Boiling

Mass Point C°
1-Propanol 60 97
Propanal 58 49
Propanone 58 56
1-Butanol 74 118
Butanal 72 76
IUPAC Name: 4-methyhexanal
Butanone 72 80
1-Pentanol 88 138 KETONES
Pentanal 86 103
2-Pentanone 86 102

First Alipathic Representatives of

Aldehydes

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Reduction
Aldehydes and ketones

Addition
Aldehydes and ketones

propanone (acetone)

Oxidation of Aldehydes
Aldehydes are easily oxidized to
carboxylic acids by a variety of oxidizing
agents, including (under some
conditions) oxygen of the air.

2-pentanone

6-methyl-3-octanone

Oxidation of Methanol
• This oxidation is catylyzed by
alcohol dehydrogenase

butanone
methyl ethyl ketone, MEK

Reactions of Aldehydes & Ketones Tollens Test

• The tollens test (silver-mirror test)
Oxidation for aldehydes is based on the
Aldehydes only

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ability of silver ions to oxidize

aldehydes.
• Ketones are negative

Tollens reagent = silver nitrate in

ammonium hydroxide Ag(NH3)2OH

remain blue: (-)

change to red: (+)

Positive Result for Silver Mirror Test

Fehling’s and Benedict’s Test

• Solutions contain 𝐶𝑢!! ions in an
alkaline medium
• In these tests, the aldehyde group
is oxidized to an acid by 𝐶𝑢!! ions.
• 𝐶𝑢!! is more stable than sliver ions
Water, Potato, Starch: negative
Glucose, Onion: positive

• Because most ketones do not give

original color: blue a positive result with Tollens,
after reacting with an aldehyde: Fehling, or Benedict solutions,
brick red precipitate these tests are used to distinguish
between aldehydes and ketones.
from cupric ions to cupric oxide
Biochemical Oxidation of Aldehydes
• When our cells ‘burn’
carbohydrates, they take
advantage of the aldehyde
reactivity.

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• The aldehyde is oxidized to a
carboxylic acid an is eventually
converted to carbon dioxide, which
is then exhaled.
• This stepwise oxidation provides
some of the energy necessary to
sustain life.

ALCOHOLS
(PHENOLS, ETHERS, & THIOLS)

Phenols
• The term phenol is used for the
class of compounds that have a Common Phenols
hydroxy group
• The parent compound is also called
phenol, C6H5OH

Naming Phenols
• Many phenols are named as
derivatives of the parent
compound, via the general
methods for naming aromatic
compounds.

Common Name: Catechol

IUPAC Name: o-dihydroxybenzene

Common Name: resorcinol

IUPAC Name: m-dihydroxybenzene

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• More acidic than alcohols and

water

Common Name: hydroquinone

IUPAC Name: p-dihydroxybenzene
Production of Phenol
• Phenol is obtained from coal tar
Common Phenolic Compounds
• Several commercial methods are
used to produce phenol
synthetically

Ethers
• Ethers have the general formula
ROR’

Ortho-phenylphenol
Disinfectant home sprays, gargles

Naming Ethers
• Individual ethers may be known by
several names

TETRAHYDROCANNABINOL – THC
Component of the marijuana plant –
Cannabis Sativa

Properties of Phenols
• Colorless, crystalline solid, mp =
41 °C IUPAC Nomenclature of Ethers
• Highly poisonous

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1. Select the longest carbon continous
chain and label it with the name of
the corresponding alkane
2. Change the –yl ending of the other
hydrocarbon group to –oxy to
obtain the alkoxy group name
e.g. CH3O – is called methoxy
3. Combine the two names from Steps
1 and 2, giving the alkoxy name Formation of Peroxides from Ethers
and its position on the longest • Oxygen of the air sloly reacts with
carbon chain first, to form the ethers to form unstable peroxides
ether name. that are subject to explosive
decomposition

Properties of Ethers
• Ethers are somewhat more polar
than alkanes, but are much less
polar than alcohols.
• Ethers – especially diethyl ether –
are exceptionally good solvents for
organic compounds.