ALCOHOL

1. Alcohols are among the most common organic compounds

2. Represent alcohols by the general formula R-OH, where R is an alkyl group.
3. Alcohols may be classified as primary, secondary, or tertiary, according to which carbon of the alkyl group is bonded to the
hydroxyl group

Other functional groups on an alcohol: 3 - bromo - 2 - pentanol

Cyclic alcohol (two -OH groups): Cyclohexan-1,4-diol

ALCOHOLS CONSTITUTIONAL ISOMERISM

Constitutional or structural isomers are compounds with the same molecular formula but different structural formula.

Examples: Butane and isobutane have the same molecular formula, C4H10, but different structural formulas.

ALCOHOLS NOMENCLATURE
Alcohols are named by both formal and common systems.
The most generally applicable system is that adopted at a meeting of the International Union of Pure and Applied Chemistry
(IUPAC) in Paris in 1957.
Derived in the same manner as those for Alkenes and alkynes, exception: the ending of the parent alkane is changed from -e to -
ol.

STEPS:
i. Identify other substituents, write the name of the substituents in
alphabetical order, and identify the position to which the -OH group bonded.
ii. Start numbering closest to the OH group
iii. Identify other substituents, write the name of the substituents in
alphabetical order, and identify the position to which the -OH group bonded.

PHYSICAL PROPERTIES OF ALCOHOLS

The lower carbon atoms are colorless liquids having a characteristic smell and
burning taste.
The more carbon atoms are more colorless and odourless.
Flammable and Produce a blue flame, NO SMOKE WHEN BURNING.

BOILING POINTS
The lower members have low boiling points but with the increase in molecular mass, the boiling points keep on increasing
gradually.
The -OH of an alcohol has a big effect on its physical properties

SOLUBILITY IN WATER
Alcohols with 3 carbons or less are miscible in water.
Alcohols with large carbon chains do not readily mix with water.

DENSITY
Generally, alcohols are lighter than water although the density increases with increase in molecular weight.

CHEMICAL REACTION OF ALCOHOLS

In a chemical reaction both the molecules and atoms, which interact with each other, are known as reactants.
Reactants usually contact each other, but if the bonds between atoms in the reactants are broken, the atoms rearrange and
form new bonds to form the products.

Dehydration or waterloss = Alcohols > Alkenes + H20

Elimination of Water molecule from alcohols to form alkenes.

Oxidation = Alcohols > Ketone > Carbonyl group

These reactions are also called dehydrogenation reactions because they involve the loss
of hydrogen from alcohol.

PHENOLS
Phenol is an aromatic organic compound with the molecular formula C₆H₅OH.
Phenols, sometimes called phenolic, they are mildy acidic
Phenolic compounds are classified as simple phenols or polyphenols based on the number of
phenol units in the molecule.

ELECTROPHILIC SUBSTITUTION REACTION OF PHENOLS

Phenols are highly prone to electrophilic substitution reactions due to rich electron density.
Electrophilic aromatic substitution reactions are the reactions where an electrophile replaces one or more hydrogen atoms
attached to the aromatic ring.

Example:
Nitration of Phenols
Phenols upon treatment with dilute nitric acid undergo nitration at low temperature (298 K) to give a mixture of ortho and para
nitrophenols.

o-nitrophenol is more volatile due to intramolecular hydrogen bonding. p-nitrophenol is less volatile and
has a high boiling point due to intermolecular hydrogen bonding.

ETHERS
Ether is a compound containing an oxygen atom bonded to two carbon atoms
Example: CH3CH2OCH2CH3 Diethyl Ether

STRCUTURE
The functional group of an ether is an atom of oxygen bonded to two carbon atoms. Figure 14.4 shows a Lewis structure and a
ball-and-stick model of dimethyl ether, CH3OCH3, the simplest ether.

NOMENCLATURE

Although the IUPAC system can be used to name ethers, chemists almost invariably use common names for low-molecular-
weight ethers. Common names are derived by listing the alkyl groups bonded to oxygen in alphabetical order and adding the
word ether. Alternatively, one of the groups on oxygen is named as an alkoxy group.

Cyclic Ether is an ether in which the ether oxygen is one of the atoms of a ring.

These ethers are known by their common names.

Ethylene oxide is an important building block for the organic chemical industry Tetrahydrofuran is a useful laboratory and
industrial solvent.

PHYSICAL PROPERTIES OF ETHERS

Ethers are polar compounds in which oxygen bears a partial negative charge and each attached carbon bears a partial positive
charge.

CHEMICAL REACTION OF ETHERS

Ethers resemble hydrocarbons in their resistance to chemical reaction. For example, they do not react with oxidizing agents,
such as potassium dichromate.

THIOALCOHOLS
Common names for simple thiols are derived by naming the alkyl group bonded to -SH and adding the
word mercaptan.
Thiols are named in the same manner as alcohols, but the suffix -e of the parent alkane is retained
and -thiol is added.
A compound that contains an -SH (sulfhydryl) group bonded to a tetrahedral carbon atom.
A common name for any molecule containing an -SH group.

PHYSICAL PROPERTIES OF THIOALCOHOLS

Because of the small difference in electronegativity between sulfur and hydrogen (2.5 - 2.1 = 0.4), an S-H bond is nonpolar
covalent. Thus, thiols show little association by hydrogen bonding. Thiols have lower boiling points and are less soluble in water
and other polar solvents than alcohols of similar molecular weight.

CHEMICAL REACTION OF THIOALCOHOLS

Thiols are weak acids (pKa = 10)
Thiols react with strong bases such as NaOH to form thiolate salts.

The most common reaction of thiols in biological systems is their oxidation to disulfides
Thiols are oxidized to disulfides by mild oxidizing agents. Reduction of a disulfide gives two thiols.
ALKENES
Alkenes are unsaturated hydrocarbons which contains C=C or carbon double bonds.
Suffix “ene”
Their structural formula is CnH_2n for molecules with one double bond (and no rings).
Alkenes are also known as olefins, after the original name for ethene, olefiant gas.

ALKENES ISOMERISM
Isomerism – Compounds that have the same molecular formula but different structural formulas
Constitutional Isomerism – Different compounds that have the same molecular formula but differ in their connectivity.

Alkenes Nomenclature
The IUPAC system for Alkene (INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY)

STEP 1: Name the longest chain that contains the C=C bond. Use the IUPAC root and the –ene ending
STEP 2: Number the longest chain so the C=C bond gets the lowest number possible.
STEP 3: Locate the C=C bond with the lower-numbered carbon.
STEP 4: Locate and name attached groups.
STEP 5: Combine all the names.
STEP 5: Combine all the names.

Cis-trans Isomerism
Cis trans are stereoisomers that have pairs of molecules which have the same formula but whose functional groups are in
different orientation.
How do you know if alkene has cis-trans isomers?
Double bond: If two groups are on the side of the double bond, the isomer is a cis alkene.
-If opposite side of the double bond, the isomer is a trans alkene

Cis-trans isomerism – also known as geometric isomerism, is a term used in chemistry that concerns the spatial arrangement of
atoms within molecules.
It is a from of alkene that have the same structure except for the orientation of the components around the double bond

Polymerization of Alkenes
Polymerization is a process by which an organic compound reacts with itself to form a high-molecular-weight compound
composed of repeating units of the original compound.
Polymers are macromolecules in which small units (monomers) are repeated again and again
Polymers are huge molecules so their molecular formulas are not written.
The simplest repeating unit in parenthesis with “n” as subscript to show the number of monomers.
Alkenes and substituted
alkenes form is an addition polymer.
• An addition polymer is a polymer in which the monomers simply "add together" with no other products formed besides the
polymer.
• Addition polymerization is similar to the addition reactions described previously except that there is no reactant other than the
alkene or substituted alkene.
Ethylene molecules are joined together in long chains.

ALKYNES

Unsaturated hydrocarbons organic molecules made of the functional group of at least one carbon-carbon triple bonds and are
written in the empirical formula of CnH2n-2.
Also known as ACETYLENE
Suffix “yne”
The IUPAC system for Alkynes
STEP 1: Name the longest chain that contains the C=C bond. Use the IUPAC root and the “yne” ending.
STEP 2: Number the longest chain so the C=C bond gets the lowest number possible.
STEP 3: Locate the C=C bond with the lower-numbered carbon.
STEP 4: Locate and name attached groups.
STEP 5: Combine all the names.
ALKYNE REACTIONS

 Addition
 Deprotonation
 Oxidative Cleavage

1. Addition
 Main pathway found in reactions of alkynes.
Breaking the C-C bond and form two new single bonds to carbon.

2. Deprotonation
 It leads alkynes to its conjugate base, an “acetylide” which is an excellent nucleophile

3. Oxidative Cleavage
 Treatment of alkynes with either ozone or KMnO4 the leads to carboxylic acids

AROMATICS

Aromatic hydrocarbons - compounds that contain sigma bonds and delocalized pi electrons between the carbon atoms in the
ring form. If the Huckel Rule is followed, a hydrocarbon can be an aromatic compound. This rule states that a compound is
aromatic if it possesses the following distinct properties: Planarity, Delocalization of the pi-electrons in the carbon ring entirely,
and a compound having (4n+2) π electrons in its structure, where n is an integer.

unsaturated hydrocarbons which have one or more planar six-carbon rings called benzene rings, to which hydrogen atoms are
attached

Nomenclature for Aromatics

1. Name the substituents followed by the name benzene.

2. If there are more than one substituents present, indicate the position by number followed by the name of the substituent
and name benzene.
-Positions 1,2 are also known as Ortho positions.
-Positions 1,3 are also known as Meta positions
-Positions 1,4 are also known as Para positions.
Chemical Reactions of Aromatic Hydrocarbons

Benzene undergoes substitution reactions instead of addition reactions due to delocalized bonding system (resonance)
Two substitutions reactions for Benzene and other aromatic hydrocarbons:
Alkylation – substituting an alkyl group into something
Halogenation – replacement of one of H atoms in benzene for a halogen atom.
NUCLEAR CHEMISTRY AND RADIOACIVITY

Radioactivity (Radioactive Decay)

Radioactivity: the spontaneous decomposition of atomic nuclei, which releases high-energy particles or rays

Radioactive decay results in a different nucleus.

• Nuclide: a nucleus with a specified number of protons and neutrons (= a specific isotope)

Isotope Symbol

Similar notation for subatomic particles

Proton
1p 0
Neutron = 1n −1
Electron = 0e

• Every element has at least one isotope whose nucleus spontaneously decomposes (radioisotope).
• A certain level of radiation naturally occurs all around us, even in our bodies (potassium-40).

Nuclear Equations

In a balanced nuclear equation, both the atomic number and the mass number must be conserved.

TYPES OF RADIO ACTIVITY

1. Alpha Particle (α) Emission

• α particle = helium nucleus 2He
• Net effect: loss of 4 in mass number, loss of 2 in atomic number

2. Beta Particle (β) Emission

3 2 P →■38(32@15)P
2 0 e → ■8(32@16)S  + ■8(   0@
−1)e■S+
8(32@15)P  → ■8(32@16)S  + ■8(  
15 16 − 1
 0@−1)e

• β particle: an electron
• Net effect: A neutron is changed into a proton

3. Gamma Ray (γ) Emission

• Gamma ray: high-energy photon of light (no charge or mass)

• Often accompanies different types of nuclear decays
• Net effect: no change in mass or atomic number

4. Positron Emission

Positron (β+): a particle with same mass as electron but opposite charge

• Net effect: A proton is changed into a neutron.

5. Electron Capture

• One of the inner-orbital electrons is captured by the nucleus.

• Net result: Changes proton into neutron.

Summary: Radioactivity

Nuclear Transmutation
• Nuclear transmutation: the change of one element into another by particle bombardment (neutron, α particle, proton,
nucleus)
• Most of the ~3300 known radioisotopes are made through artificial nuclear transmutation in particle accelerators.

HALF LIFE

Detection of Radioactivity
• Geiger-Muller counter: High-energy particles ionize argon; argon ions can conduct electricity

• Scintillation counter: Uses a substance that gives off light when struck by high-energy particles
• Thermo luminescent dosimeters: Electrons excited by high-energy particles are trapped in crystals, then heated to relax into
ground state and emit light

Application: Radiocarbon Dating (C-14 Dating)

Half-life of 14C = 5715 years
• Atmosphere has constant amount of 14C.
• 14C content in a living plant is constant due to constant uptake of 14CO2 by plant.
• At moment of death, plant 14C decays without replenishment.
• So 14C content of fossil tells how much Dme has passed since the plant died (age).

U-238 Decay Series

In many cases, daughter nuclides are also radioactive.

EFFECTS OF RADATION ON LIFE

DAMAGING EFFECTS OF RADIATION

• Ionizing power: ability of radiation to ionize molecules and atoms. More massive particles have more potential to interact with
and ionize other molecules.
• Penetrating power: ability of radiation to penetrate matter. Smaller particles can penetrate more deeply.

Types of Radiation Damages

• Acute radiation damage: damage to cells resulting from exposures to large amounts of radiation in short period of time
• Increased cancer risk: Lower radiation doses over a longer period of time can cause damage to somatic cells and increase
cancer risk.
• Genetic defects: damage to DNA in reproductive cells that shows effect in offspring

Effects of Short-Term Radiation Exposure

Rem: A unit that indicates biological damage of radiation

Biological Effects of Radiation

Typical Radiation Exposure in U.S.

Nuclear Medicine Application: Radiotracers

• Radiotracers: radioactive nuclides that can be put into organisms through food or drugs, and be traced for medical diagnostic

Radiotracers in PET Scans

PET: positron emission tomography
• Examples of positron-producing isotopes: 18F, 11C
• These radioactive isotopes are attached to glucose.
• Areas of brain rapidly consuming these radiotracers “light up” on PET
screen.
• Short half-lives (110 min for 18F, 20 min for 11C) require speedy synthesis.

Nuclear Medicine Application: Radiotherapy

• Gamma rays are used to kill rapidly dividing cancer cells.
• Patients undergoing radiotherapy develop symptoms of radiation sickness (vomiting, hair loss, skin burns).