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COMPILED NOTES IN BASIC ORGANIC CHEMISTRY FOR BOTH LEC AND LAB

COMPILED BY: Luke Mondares, RPh (College of Pharmacy)

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.

ORGANIC FLAMMABILITY Yes No COMPOUNDS VS


INORGANIC COMPOUNDS
BOILING POINT Low High

SOLUBILITY IN Insoluble Soluble


WATER
SOLUBILITY IN Soluble Insoluble
ORGANIC (majority)
SOLVENT
TYPES OF Covalent Ionic
BONDING

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

CLASSIFICATION OF CARBON ATOMS A secondary carbon atom is a carbon atom in


an organic molecule that is directly
bonded to two other carbon atoms. A propane
Each of the carbon atoms within a hydrocarbon molecule contains a secondary carbon
structure can be classified as a atom as well as two primary carbon atoms.
primary (1º), secondary (2º), tertiary (3º), or
quaternary (4º) carbon atom. CH3 CH2 CH3
1°C 2°C 1°C
A primary carbon atom is a carbon atom in
an organic molecule that is directly A tertiary carbon atom is a carbon atom in
bonded to one other carbon atom. Both carbon an organic molecule that is directly
atoms in ethane are primary carbon bonded to three other carbon atoms.
atoms.

CH3CH3
B. UNSATURATED

A quaternary carbon atom is a carbon atom in an


organic molecule that is directly
bonded to four other carbon atoms.

CHEMISTRY
AT A GLANCE
TYPES OF FORMULA:

I. HYDROCARBONS

TWO TYPES OF HYDROCARBONS:


A. SATURATED
NOMENCLATURE OF
HYDROCARBONS (IUPAC)

SATURATED HYDROCARBONS UNSATURATED HYDROCARBONS


All are Single bonds Presence of Double or Triple bonds

Examples: Alkanes, Cycloalkanes Examples: Alkenes, Alkynes


Heptane 2 hexyne

2 methyl hexane
Cyclohexene
Solid at room temp Liquid at room temp

Source: Usually Animal Fats/Oils Source: Usually Vegetable Fats/Oils

Bad Fatty acids Good Fatty acids

These Fatty acids tend to accumulate in Can reduce cholesterol


the blood vessels leading to
atherosclerosis.(Risk of heart attack)
EX: Palmitic Fatty acid Ex: Linolenic Fatty acid (Omega-3)

1. ALKANES

Formal IUPAC rules for naming


branched-chain alkanes are as follows:

Rule 1: Identify the longest continuous


carbon chain (the parent chain), which
may
or may not be shown in a straight
line, and name the chain.
Rule 2: Number the carbon atoms in the group must be included. These
parent chain from the end of the chain position numbers, separated by commas,
nearest a substituent (alkyl group). precede
There are always two ways to number the numerical prefix. Numbers
the chain (either from left to are separated from words by hyphens.
right or from right to left). This rule
Note that the numerical prefi x di-
gives the first-encountered alkyl
must always be accompanied by two
group(is the group of atoms that would be
obtained by removing a numbers, tri- by three, and so on, even
hydrogen atom from an alkane) the lowest if the same number is written
possible number. twice, as in 3,3-dimethylpentane

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.

Rule 4: If two or more of the same kind


of alkyl group are present in a molecule,
indicate the number with a
Greek numerical prefix (di-, tri-, tetra-,
penta-,
and so forth). In addition, a
number specifying the location of each
identical
Rule 6: Follow IUPAC punctuation
rules, which include the following: (1)
Separate
numbers from each other by
commas. (2) Separate numbers from
letters
by hyphens. (3) Do not add a
hyphen or a space between the last-
named
substituent and the name of the 2. CYCLOALKANES
parent alkane that follows.

IUPAC naming procedures for


cycloalkanes are similar to those for
alkanes. The
ring portion of a cycloalkane molecule
RULE 7: NOMENCLATURE OF serves as the name base, and the prefix
HALOGENATED ALKANES cyclo- is used to indicate the presence of
1. Halogen atoms, treated as the ring. Alkyl substituents are named in
substituents on a carbon chain, are the same manner as in alkanes.
called fluoro-, Numbering conventions used in locating
chloro-, bromo-, and iodo-. substituents
2. When a carbon chain bears both a on the ring include the following:
halogen and an alkyl substituent,
the two A. If there is just one ring
substituents are considered of substituent, it is not necessary to
equal rank in determining the numbering locate it by number.
system
for the chain. The chain is B. When two ring substituents are
numbered from the end closer to a present, the carbon atoms in the
substituent, ring are numbered
whether it be a halo- or an alkyl beginning with the substituent of
group. higher alphabetical priority and
3. Alphabetical priority determines proceeding
the order in which all substituents in the direction (clockwise or
present counterclockwise) that gives the other
are listed. substituent the lower number.
C. When three or more ring
substituents are present, ring
numbering begins at
the substituent that leads to the
lowest set of location numbers. When
two or
more equivalent numbering sets
exist, alphabetical priority among
substituents
determines the set used.

Rule 3. Number the parent carbon chain


beginning at the end nearest the double
bond.

Rule 4. Give the position of the double


bond in the chain as a single number,
which
is the lower-numbered carbon
atom participating in the double bond.
This
3. ALKENES AND CYCLOALKENES number is placed immediately
before the name of the parent carbon
chain.
Rule 1. Replace the alkane suffix -ane
with the suffix -ene, which is used to
indicate
the presence of a carbon–carbon
double bond.
Rule 2. Select as the parent carbon
chain the longest continuous chain of Rule 5. Use the suffi xes -diene, -triene,
carbon atoms -tetrene, and so on when more than one
that contains both carbon atoms double bond is present in the
of the double bond. For example, molecule. A separate number must be
select used
to locate each double bond.
Rule 6. A number is not needed to locate The IUPAC system of naming
the double bond in unsubstituted monosubstituted benzene derivatives
cycloalkenes with only one uses the
double bond because that bond is name of the substituent as a prefix to the
assumed to name benzene. Examples of this type of
be between carbons 1 and 2. nomenclature include
Rule 7. In substituted cycloalkenes with
only one double bond, the double-
bonded
carbon atoms are numbered 1
and 2 in the direction (clockwise or
counterclockwise)
that gives the first-encountered
substituent the lower number.
Again, no number is used in the
Note: Some monosubstituted benzene
name to locate the double bond.
have their own common names like
toluene (instead of Methylbenzene)

Benzene Derivatives with Two


Substituents
When two substituents, either the same
or different, are attached to a benzene
Rule 8. In cycloalkenes with more than ring,
one double bond within the ring, assign three isomeric structures are possible.
one
double bond the numbers 1 and 2
and the other double bonds the lowest
numbers possible.

To distinguish among these three


isomers, the positions of the substituents
relative
to one another must be specified. This
can be done in either of two ways: by
4. ALKYNES using
 Same set of rules for the numbers or by using nonnumerical
alkenes. Just change “ene” to
“yne”
prefixes.
 Propene to Propyne When numbers are used, the three
isomeric dichlorobenzenes have the first
5. AROMATIC listed
set of names:
Benzene Derivatives with One
Substituent
C1 - C3 are polar
C3 > are nonpolar

Example: (Solubility in H2O trend)

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

Hexyne > Cyclohexene > Hexane >


Toluene

Note: A circle in a benzene ring


indicates three double bonds which
can resonate

ACTIVITY#14: HYDROCARBONS SOLUBILITY IN ALCOHOL(Non-polar)

PROPERTIES OF HYDROCARBONS The following are miscible in


alcohol:
1. SOLUBILITY Hexane
Two factors that affect the solubility of 1 Hexyne
Hydrocarbons are: Cyclohexene
Toluene
A) LENGTH OF CARBON CHAIN
Toluene > Hexane > Cyclohexene >
↑ Carbon chain length = ↑ Non-polarity 1 Hexyne
The longer the carbon chain, the 3. BOILING POINT
more nonpolar it becomes
The longer the carbon chain, the higher
2. DENSITY the boiling point
C1 – C4 exists as gases
- Almost all organic compounds,
C5 - C11 exists as liquids
such as cooking oil, are less denser
C11 –Carbons greater than 11 are solids
than water
- Organic compounds have a density
less than 1g/mL

FACTOR AFFECTING  Addition reaction


BOILING PT:  Breaking down of
double bonds
BRANCHING(Substituents)
↑ branch = ↓ boiling point
↓ branch = ↑boiling point
TYPES OF ADDITION
F
CH3 – CH – CH – CH3
Br *SYMMETRICAL (IDENTICAL ATOMS)
2 bromo 3 methyl butane Example: Br2, H2, O2

CH3CH2CHCH3 *UNSYMMETRICAL (UNIDENTICAL)


Cl Example: HCl, H2O, HF
2 chlorobutane

Markovnikov’s Rule: A hydrogen atom will


*2 chlorobutane has a higher
attach to the carbon that has more H atoms.
boiling point than 2 bromo 3
methyl butane Ex: Adding HBr to 1-Propene [2-possible
products can be formed, but one of it is
Reason: The more branched incorrect(red)]
hydrocarbon has lesser surface area

CHEMICAL PROPERTIES OF CH3 – CH = CH2 + HBr CH3 – CH - CH3


HYDROCARBONS
(CORRECT)
1.) Halogenation Br
 F, Cl, Br, I, At
 “Substitution Reaction” or CH3 – CH2 – CH2
– Exchange of atoms
(INCORRECT)
H H
Br
H – C – H – Br2  H – C – Br + HBr
H H

ALKYNES
HALOGENATION OF
ALKENES Alkyne  Alkene  Alkane
1 Hexyne: Reacts

Cyclohexene: Reacts

AROMATIC CHEMICAL REACTIONS


*Substitution reaction

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.

IUPAC rules for naming alcohols that


contain a single hydroxyl group follow.

Rule 1: Name the longest


carbon chain to which the hydroxyl
group is attached.
The chain name is
obtained by dropping the final -e from
the alkane
name and adding the
suffix -ol.
Rule 2: Number the chain
starting at the end nearest the hydroxyl
group, and use
the appropriate number
to indicate the position of the OH
ACTIVITY#15: Alcohol and Phenols
group.
(In numbering of the
longest carbon chain, the hydroxyl PHYSICAL PROPERTIES
group has
1) Solubility
precedence over
(“outranks”) double and triple bonds, as OH is polar
well as over
alkyl, cycloalkyl, and Carbon chain is
non-polar
halogen substituents.)
Rule 3: Name and locate any Methanol + Water = Soluble
other substituents present.
Rule 4: In alcohols where the Ethanol + Water = Soluble
OH group is attached to a carbon atom
in a ring, the Propanol + Water = Soluble
ring is numbered Butanol + Water = Insoluble
beginning with the OH group.
Numbering then proceeds Phenol + Water = Soluble
in a clockwise or Phenol has 7 carbons but is soluble
counterclockwise direction to give the based on the cyclic structure
next substituent
A. Length of Carbon Chain
C1 – C3 are polar
3° : turbid immediately
C4 and above are non-polar 2° : takes a few minutes
1 ° : No reaction

B. TYPES OF ALCOHOL FERRIC CHLORIDE TEST


 Primary Alcohol -used to detect the presence of Phenol
 Secondary Alcohol Result: positive red or blue
 Tertiary Alcohol
1 ° > 2 ° > 3° CHROMIC ACID
Reason: Primary alcohols can easily -known as Jones Reagent
form H-bond with water due to less stearic -detects presence of 1 ° and 2° Alcohol
hindrance (Alkyl group)
IODOFORM TEST
-also known as Triiodomethane
-detects the presence of methyl ketones
-If positive, it will produce a yellow color
-has a medical odor / hospital-like odor
-used as an antiseptic

Ethanol – oxidized into an aldehyde (Ethanal


which has methyl ketone in its structure)
- Only alcohol positive to Iodoform
test

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

Rule 1: Select the longest


carbon chain and use its name as the
Rule 2: For symmetrical ethers, name base name.
the alkyl group, add the prefi x di-, and Rule 2: Change the -yl
then ending of the other hydrocarbon group
to -oxy to obtain the
alkoxy group name; alkane to -oic acid.
methyl becomes methoxy, ethyl Rule 3: Number the parent
becomes ethoxy, etc. chain by assigning the number 1 to the
Rule 3: Place the alkoxy carboxyl carbon
name, with a locator number, in front of atom, but omit this
the base number from the name.
chain name. Rule 4: Determine the identity
Two examples of IUPAC and location of any substituents in the
ether nomenclature, with the alkoxy usual manner,
groups present and append this
highlighted in each information to the front of the parent
structure, are: chain name.
Rule 5: If the carbonyl group is
bonded to a carbon ring, name the ring
and add
the words carboxylic
acid. The carbon bearing the carboxyl
group is
always carbon 1.
Locate any other ring
substituents in the usual
manner.
B. CARBOXYLIC
ACIDS

IUPAC rules for naming carboxylic


acids resemble those for naming
aldehydes

Monocarboxylic Acids
 A monocarboxylic acid is a
carboxylic acid in which one
carboxyl group is present.

IUPAC rules for naming such


compounds are:

Rule 1: Select as the parent


carbon chain the longest carbon chain Dicarboxylic Acids
that includes  A dicarboxylic acid is a
the carbon atom of the carboxylic acid that contains two
carboxyl group. carboxyl groups, one at
Rule 2: Name the parent chain each end of a carbon chain.
by changing the -e ending of the Saturated acids of this type are named
corresponding by appending
the suffix -dioic acid to the
corresponding alkane name (the -e is
retained to facilitate
pronunciation). Both carboxyl
carbon atoms must be part of the parent
carbon
chain, and the carboxyl locations This is the basis for the rules used in
need not be specifi ed with numbers determining both common and IUPAC
because names
they will always be at the two for esters. The rules are as follows:
ends of the chain. Rule 1: The name for the alkyl
part of the ester appears fi rst and is
followed by a
separate word giving the
name for the acyl part of the ester.
Rule 2: The name for the alkyl
part of the ester is simply the name of
the R group
(alkyl, cycloalkyl, or
aryl) present.
Rule 3: The name for the acyl
part of the ester is obtained by
dropping the -ic acid
ending for the acid’s
Aromatic Carboxylic Acids name and adding the suffi x -ate.
 The simplest aromatic carboxylic
acid is called benzoic acid

C. ESTERS

Act. #17: Carboxylic Acids and


Nomenclature for Esters its Derivatives & Esters and
For naming purposes, an ester may be Ethers
viewed structurally as containing an
acyl
group and an alkyl group.
CARBOXYLIC ACIDS
has a general formula of:
O
R - C – OH

Its derivatives are:


a) Amides
0.2g NaCH3COO

b) Anhydrides Add water (H2O)

Test in Litmus Paper


c) Esters

Observe

Result: Red litmus paper turns into blue


d) Acyl halides while the blue litmus paper remains blue.
-not common Therefore, it is a basic solution
SALT FORMATION
(NEUTRALIZATION)
0.2 Benzoic acid NaCH3COO + H2O  NaOH + CH3COOH
 Na⁺ + CH3COO⁻ + OH⁻ + H⁺

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.

Tertiary amine is an amine in which


the nitrogen atom is bonded to three
hydrocarbon
Urea is one of the waste product of the urine.
It is a by product of the breakdown into groups and no hydrogen atoms. The
ammonia. generalized formula for a tertiary amine
is
Concentrated urine
R3N; three carbon–nitrogen bonds are
-has a strong pungent odor present.
-result to the formation of kidney stones
-is produced because of the ountercurrent NOTE: The basis for the amine
multiplication in the kidneys; “kidney primary-secondary-tertiary
process” classification system differs
- indicates dehydration from that for alcohols

V. AMINES AND AMIDES

A. AMINES

Structure and Classification of Amines


Amines are classified as: primary (1°),
secondary (2°), or tertiary (3°) on the
basis of how many hydrocarbon
Nomenclature for Amines
groups have replaced ammonia A. COMMON
hydrogen atoms B. IUPAC
A. COMMON Rule 4: The position of
attachment of the nitrogen
In the common system of
atom is indicated by a number
nomenclature, amines are named
in front of the parent
by listing the alkyl group or
chain name.
groups
Rule 5: The identity and
attached to the nitrogen atom
location of any substituents
in alphabetical order and
are appended to the front of
adding the suffix -amine;
the parent chain name.
all of this appears as one
word. Prefixes such as di- and
tri- are added when identical
groups are bonded to the
nitrogen atom.
Secondary and tertiary
amines are named as N-substituted
primary amines.
The largest carbon group bonded
to the nitrogen is used as the parent
amine name.
B. IUPAC The names of the other groups
The IUPAC rules for naming attached to the nitrogen are appended to
amines are similar to those for the front
alcohols of the base name, and N- or N,N-
(Alcohols are named as prefixes are used to indicate that these
alkanols and amines are groups are
named as alkanamines. attached to the nitrogen atom
rather than to the base carbon chain.
IUPAC rules for naming
primary amines are as
follows:

Rule 1: Select as the parent


carbon chain the longest
chain to which the nitrogen
atom is attached.
Rule 2: Name the parent
chain by changing the -e The simplest aromatic amine, a
ending of the corresponding benzene ring bearing an amino group, is
alkane name to - called
amine. aniline Other simple aromatic
Rule 3: Number the parent amines are named as derivatives of
chain from the end nearest the aniline.
nitrogen atom.
REFERENCES: SWU-COP MANUALS,
STOKER, DENNISTON, CENTRAL
SCIENCE
B.AMIDES
 Rules for naming Amides are
similar to Amines. Just change
“amine” to “amide”
 Butanamine to Butanamide

ACTIVITY 18: Amides & 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

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