ORGANIC CHEMISTRY
Branch of chemistry that deals with the structure, properties, composition, reactions, and
preparation of Carbon containing compounds/molecules.
FRIEDRICH WOHLER
Disprove vitalism theory (stated that inorganic materials did not contain the "vital force" of
life )
Accidentally synthesized urea( CH4N2O) from his attempt to prepare ammonium cyanate from
silver cyanide PROPERTY ORGANIC INORGANIC and ammonium chloride.
CARBON
TYPES OF ORGANIC COMPOUNDS
Group IVA (14)
1. HYDROCARBONS
King of all elements
2. HYDROCARBON DERIVATIVES
Atomic number: 6
Atomic mass: 12.001 g/mol
Has a unique ability to form bonds with
HYDROCARBONS
itself, known as catenation.
Organic compound consisting entirely
Valence shell: Contain 4 electrons in its
of hydrogen and carbon
outermost shell
EX:
Needs four more electrons to achieve
1. ACYCLIC FORM
octet rule therefore forming four more
A. Alkanes (CnH2n+2)- All are
bonds.
single bonds
10 Common alkanes:
halogen atoms (elements in column
7A)
EX:
1. OXYGEN CONTAINING
A. Alcohols (R-OH)
B. Aldehydes (R-CHO)
C. Ketones (R-CO-R)
D. Ether (R-O-R)
E. Ester (R-COO-R)
F. Carboxylic acid (R-COOH)
2. NITROGEN CONTAINING
A. Amines (R-NH2)
B. Amides (R-CONH2)
C. Imide (RN=C=NR)
B. Alkenes (CnH2n)- Contain 3. SULFUR CONTAINING
double bond/s A. Thiols (R-SH)
C. Alkynes (CnH2n-2)- Contain B. Thioethers (R-S-R)
triple bond/s 4. HALOGEN CONTAINING
2. CYCLIC FORM A. Alkyl halide (R-X)
A. Cycloalkanes (CnH2n)
B. Cycloalkenes (CnH2n-2) EXAMPLE! IDENTIFY
C. Cycloalkyne- Possible only THE FUNCTIONAL
when the number of carbon GROUPS PRESENT IN
atoms in the ring is large THE STRUCTURE OF
enough to confer the CARVEDILOL, A BETA-
flexibility necessary to BLOCKER
accommodate this geometry. ANTIHYPERTENSIVE
Cyclooctyne (C8H12) is the DRUG.
smallest cycloalkyne capable
of being isolated and stored
as a stable compound.
D. Aromatic compounds-
Benzene containing rings
HYDROCARBON DERIVATIVES
Contain at least one element other
than hydrogen or carbon, such as
oxygen, nitrogen or one of the
ANSWER: 1°C 1°C
CH3CH3
B. UNSATURATED
CHEMISTRY
AT A GLANCE
TYPES OF FORMULA:
I. HYDROCARBONS
2 methyl hexane
Cyclohexene
Solid at room temp Liquid at room temp
1. ALKANES
Rule 3: If only one alkyl group is Rule 5: When two kinds of alkyl groups
present, name and locate it (by number), are present on the same carbon chain,
and number each group separately,
prefix the number and name to and list the names of the alkyl groups in
that of the parent carbon chain. alphabetical order.
Ethane>Pentane>Hexane
B) PRESENCE OF BONDS
The prefix system uses the prefixes Solubility in Water
ortho-, meta-, and para- (abbreviated o-, Alkynes > Alkenes > Alkanes
m-,
and p-). Example:
Ortho- means 1,2 disubstitution; the Hexyne > 2 methyl pentene >
substituents are on adjacent carbon hexane
atoms. Reason:
Meta- means 1,3 disubstitution; the Triple bonds´ hydrocarbon
substituents are one carbon removed geometry (Linear) creates more
from dipole moment than Double bonds´
each other. (Trigonal planar) and Single bonds´
(Tetrahedral)
Para- means 1,4 disubstitution; the
substituents are two carbons removed SOLUBILITY IN
from WATER(Polar)
each other (on opposite sides of
the ring). Hexane – has 6 C
1 Hexyne – has 6 C
Cyclohexene – has 6 C
Toluene– has 7 C
ALKYNES
HALOGENATION OF
ALKENES Alkyne Alkene Alkane
1 Hexyne: Reacts
Cyclohexene: Reacts
Bromine Water
– Reddish brown in nature
– Disappearance of color indicates the Toluene Benzoic Acid
presence of a double bond
Detection of Alkanes:
Toluene: POSITIVE
Hexane: NEGATIVE
1 Hexyne: NEGATIVE
Cyclohexene: POSITIVE
Hexane
REACTION w/ KMnO4
(POTASSIUM PERMANGANATE)
Saturated Hydrocarbons: NO Reaction Reaction with Sulfuric Acid
Unsaturated Hydrocarbon: Reacts Saturated Hydrocarbons: No reaction
Unsaturated Hydrocarbons: React
Toluene: Reacts Toluene: Reacts
Hexane: NO Reaction Hexane: NO Reaction
1 Hexyne: Reacts the lower number. The
Cyclohexene: Reacts number “1” (for the hydroxyl group) is
omitted
from the name since by
II. ALCOHOLS AND definition the hydroxyl-bearing carbon
PHENOLS is carbon 1.
OTHER INFORMATIONS:
Oxidation of alcohols Note:
A. Primary alcohols Aldehydes There are NO presence of methyl ketone in
Carboxylic acid propanol, butanol and phenols even when they
Ex: Ethanol Ethanal are oxidized
(Acetaldehyde) Ethanoic acid
(Acetic acid)
*Ethanal responsible for hangover
B. Secondary alcohols Ketone
C. Tertiary alcohols No reaction III. ALDEHYDES AND
KETONES
Contains Carbonyl group
Reduction (C=O)
Reverse of the oxidation Note: Other functional
process groups having carbonyl
group include: Carboxylic
LUCAS TEST acids, Esters, and Amides
-detects the presence of 2° & 3° Alcohol
-based on the presence of turbidity
-Reactivity 3° > 2 ° > 1 ° A. ALDEHYDES
Nomenclature for Aldehydes
In IUPAC nomenclature, aldehydes are
named using the suffix -al. Note the
closeness
of this suffix to that used for naming
alcohols, -ol. The two suffixes are often
confused with each other. The suffix -al
(pronounced like the man’s name Al)
denotes
an aldehyde; the suffix -ol (pronounced
like the ol in old) denotes an alcohol.
The IUPAC rules for naming aldehydes
are as follows:
Rule 1: Select as the parent carbon Rule 6: In the IUPAC system, aromatic
chain the longest chain that includes aldehydes—compounds in which an
the aldehyde
carbon atom of the carbonyl group is attached to a benzene
group. ring—are named as derivatives of
Rule 2: Name the parent chain by benzaldehyde, the
changing the -e ending of the parent compound
corresponding
alkane name to -al.
Rule 3: Number the parent chain by
assigning the number 1 to the carbonyl
carbon
atom of the aldehyde group. The
number 1, however, does not become
part
of the name.
Rule 4: Determine the identity and
location of any substituents, and
append this B. KETONES
information to the front of the
parent chain name. Nomenclature for Ketones
Rule 5: When an aldehyde functional Assigning IUPAC names to ketones is
group is attached to a carbon ring, similar to naming aldehydes except that
name the the ending -one is used instead of -al.
ring and add the suffi x - The rules for IUPAC ketone
carbaldehyde. nomenclature
follow:
Rule 1: Select as the parent carbon
chain the longest carbon chain that
includes
the carbon atom of the carbonyl
group.
Rule 2: Name the parent chain by
changing the -e ending of the
corresponding
alkane name to -one. This
ending, -one, is pronounced “own.”
Rule 3: Number the carbon chain such
that the carbonyl carbon atom receives
the
lowest possible number. The
position of the carbonyl carbon atom is
noted
by placing a number
immediately before the name of the
Act. #16: Aldehydes and Ketones
parent chain.
Rule 4: Determine the identity and TOLLENS TEST
location of any substituents, and -known as Silver Mirror test
append this
-has AgNO3 which is an oxidizing
information to the front of the agent
parent chain name.
Rule 5: Cyclic ketones are named by -positive to aldehydes but negative to
ketones
assigning the number 1 to the carbon
atom of the carbonyl group. -Reason: Aldehydes can be oxidized
Numbering then proceeds in a while ketones are not
clockwise or Aldehydes Acids
counterclockwise direction to
Ketones No reaction
give the next encountered substituent
the -positive to primary alcohols
lower number. The “1,”
designating the carbonyl carbon atom
Benzaldehyde: Positive
location,
is omitted from the name. Acetone (Dimethyl ketone): Negative
Cyclohexanone: Negative
Methylbutanal: Positive
IODOFORM TEST
Positive only to
Acetone(diMETHYL
KETONE)
add the word ether, separating
the words with a space. Such ether
names
have two separate words within
them.
IV. ETHERS, Carboxylic
Acids and its Derivatives:
Esters
A. ETHERS
A2. IUPAC Names
Ethers with more complex
Two ways of naming:
alkyl/aryl groups are
A1. COMMON NAME named using the IUPAC
A2. IUPAC system.
In this system, ethers are
named as substituted hydrocarbons. The
A1. Common names smaller
are almost always used for hydrocarbon attachment
ethers whose alkyl groups and the oxygen atom are called an
contain four or alkoxy group, and
fewer carbon atoms. There this group is considered a
are two rules, one for unsymmetrical substituent on the larger hydrocarbon
ethers (two different group. An alkoxy
alkyl/aryl groups) and one group is an OR group, an
for symmetrical ethers (two identical alkyl (or aryl) group attached to an
alkyl/aryl groups). oxygen atom. Simple
alkoxy groups include the
Rule 1: For unsymmetrical ethers, following:
name both hydrocarbon groups bonded
to the
oxygen atom in alphabetical
order and add the word ether,
separating the The general symbol for an
words with a space. Such ether alkoxy group is R-O- (or
names have three separate words RO-).
within them.
The rules for naming an
ether using the IUPAC
system are
Monocarboxylic Acids
A monocarboxylic acid is a
carboxylic acid in which one
carboxyl group is present.
C. ESTERS
Observe
3mL 10% NaOH 3mL Water Note: NaOH is a strong base (100%
dissociation)
observe observe
Strong Acid + Strong Base = Neutral
Strong Base + Weak Acid = Basic salt
Insert balance equation/structure
Strong Acid + Weak Base= Acidic salt
BENZOIC ACID + NaOH Weak Acid + Weak Base = No reaction
NaBenzoate + H20
*will depend on the equilibrium constant,K
Sodium Benzoate
-used as preservatives in the market
ESTERS
Examples: Syrup
1mL butanol
SALT HYDROLYSIS
Hydro- means water
-Lysis means breaking down Acetamide
(drop by drop)
∴ Hydrolysis is the process of breaking down
molecules with the use of water.
Add water Primary amine
Is an amine in which the nitrogen atom
is bonded to one hydrocarbon group
Note the odor
and two
hydrogen atoms. The generalized
Esterification formula for a primary amine is RNH2;
one
-conversion of carboxylic acids to esters using acid carbon–nitrogen bond is present.
and alcohols; carboxylic acid + 1° alcohol
Secondary amine
O is an amine in which the nitrogen atom
is bonded to two hydrocarbon groups
Insert CH3-C-OH + H2O ->
CH3COOH+NH3 and one hydrogen atom. The
generalized
formula for a secondary amine is
R2NH; two carbon–nitrogen bonds are
present.
A. AMINES
Amines
-derivatives of ammonia generally by
nitrogen atom joined in at least one
alkyl group. R-NH2
Amides
-compounds that have a carbonyl group
in between nitrogen and the alkyl group
Solubility in Water:
*Amides&Amines fall off as the
hydrocarbon chains get longer after 6
carbons
* Trend: PRIMARY> SECONDARY>
TERTIARY
Reason: Primary amines can
easily form H-bond with water due to
less stearic hindrance
Basicity:
Trend:
SECONDARY>TERTIARY>PRIMAR
Y