[LEC] UNIT 09: ALKYL HALIDES

○ Number the parent chain to give the substituent

OUTLINE
encountered first the lower number.
I STRUCTURE OF ALKYL HALIDES
○ Show halogen substituents by the prefixes fluoro-,
II USES OF ALKYL HALIDES chloro-, bromo-, and iodo- and list them in
III NOMENCLATURE alphabetical order with other substituents.
IV REACTIONS OF ALKYL HALIDES ○ Locate each halogen on the parent chain
A Nucleophilic Substitution
B β-Elimination

STRUCTURE OF ALKYL HALIDES

● Alkyl Halide (Haloalkane): Compound containing a
halogen atom covalently bonded to an sp3 hybridized
carbon
o Given symbol: RX
■ R: Alkyl ● Several polyhaloalkanes are common solvents and are
■ X: Halide generally referred to by their common or trivial names

CONDENSED
IUPAC NAME COMMON NAME STRUCTURAL
FORMULA
Dichloromethane Methylene Chloride CH2Cl2
Trichloromethane Chloroform CHCl3
USES OF ALKYL HALIDES 1,1,1-Trichloroethane Methyl Chloroform CH3CCl3,
● Solvents: Degreasers and dry cleaning fluid Trichloroethylene Trichlor CCl2=CHCl
● Reagents for synthesis of other compounds
○ Because alkyl halides can easily react with different REACTIONS OF ALKYL HALIDES
materials and solvents ● The halogen atom may leave with its bonding pair of
■ Halides can easily be removed electrons to give a halide ion which is table
● Anesthetic: ○ A halide is called a good leaving group
○ Halothane (CF3CHClBr): a general anesthetic ■ Once halides are detached from the carbon
■ CHCl3 was originally used but it was toxic and chain they become very stable
carcinogenic ○ The carbon removed originally attached to the halide
● Freons: Chlorofluorocarbons (CFCs) becomes a carbocation
○ Used in refrigerators to remove heat and lower ■ Carbocation: Carbon with a positive charge
temperature ■ Becomes attractive to nucleophiles due to the
○ Freon 12 (CF2Cl2): originally used positive charge
■ Replaced with Freon 22 (CF2CHCl) because it is ● Types of Reactions of Alkyl Halides:
not harmful to the ozone layer. ○ Nucleophilic substitution: If an atom replaces the
● Pesticides: DDT (Dichlorodiphenyltrichloroethane) halide the overall reaction
○ Banned in US ■ Nucleophiles are attracted to carbocations
■ Nucleophiles have a negative charge
FREONS ○ β-Elimination: If the halide loss is accompanied by
● Freons are Chlorofluorocarbons (CFCs) the loss of another atom
○ Among the most widely used are/were: ■ Accompanied by a positive charge Hydrogen that
■ Trichlorofluoromethane (Freon-11): CCl3F forms a double bond
■ Dichlorodifluoromethane (Freon-12): CCl2F2 ■ Alpha (ɑ) carbon: Carbon where the halide is
● Much lower ozone-depleting alternatives are the: attached to
○ Hydrofluorocarbons (HFCs) ■ Beta (β) carbon: Carbon next to the alpha
■ HFC-134a: CH2FCF3
○ Hydrochlorofluorocarbons (HCFCs)
■ HCFC-141b: CH3CCl2F

NOMENCLATURE
● Steps in naming Alkyl Halides:
○ Locate the parent alkane

QUEMQUEM, EVGV 1
 TRANS: ALKYL HALIDES

NUCLEOPHILIC SUBSTITUTION
● General Nucleophilic Substitution (SN)

● Two limiting mechanisms for nucleophilic substitutions:

○ SN2: Bimolecular
■ Two species are involved in the rate determining
step
■ Two species of nucleophile are binded to the
carbon
○ SN1: Unimolecular SN1 REACTIONS
■ Only one species is involved in the ● Bond breaking between carbon and the leaving group is
rate-determining step entirely completed before bond forming with the
nucleophile begins
○ Halide is removed forming a carbocation intermediate
○ Then, nucleophile binds to the carbocation
● Rate = k[RX]
● In an energy diagram for an SN1 reaction, there are two
transition states and one intermediate

SN2 REACTIONS
● Both reactants are involved in the transition state of the
rate-determining step
○ Both the halide and nucleophile are involved in the
transition state
● Rate = k[RX][Nu–]
● The nucleophile attacks the reactive center
○ Nucleophile binds to the carbon before cleavage of PROCESS OF SN1 REACTIONS
the halide ● Step 1: Break a bond to form a stable ion or molecule
○ Ionization of the C-X bond gives a carbocation

● In an energy diagram for an SN2 reaction, there is one

● Step 2: Reaction of a nucleophile and an electrophile to
transition state and no reactive intermediate
form a new covalent bond
○ Increase in energy level due to the binding of the
○ Nucleophilic Attack which forms the bond
nucleophile to the carbon

QUEMQUEM, EVGV 2
 TRANS: ALKYL HALIDES

SN1 & CARBOCATION REARRANGEMENTS ○ Governed by Steric Factors: Relative ease of

● When an SN1 reaction occurs from a 2o haloalkane, a 2o approach of the nucleophile to the site of reaction
carbocation is formed, which is prone to rearrange to a ■ More substituents means that it will not follow SN2
more stable 3o carbocation reaction
○ Occurs in the presence of a base ○ Relative rates: methyl > 1° > 2° > 3°
● Process: ■ 3° almost never react by SN2
○ Bond Breaking ■ 2° depends on the solvent
■ Halide is cleaved
○ Rearrangement from a secondary carbocation to a
tertiary carbocation to become more stable
■ Alkyls move and rearrange
○ Nucleophilic attack

FACTORS AFFECTING RATE OF REACTIONS

● Points of comparison between SN1 and SN2
○ Nature of Nucleophile
○ Nature of Haloalkane
○ Nature of Leaving Group
○ Nature of Solvent

NATURE OF NUCLEOPHILE ● Steric Factors

○ Compare access to the reaction center in
● Nucleophilicity: A kinetic property measured by the rate
bromoethane and 2-bromo-2-methylpropane
at which a Nu– attacks a reference compound under a
(tert-butyl chloride)
standard set of experimental conditions.
○ Ex: Rate at which a set of nucleophiles displaces
bromide ion from bromoethane in ethanol at 25oC
■ CH3CH2Br + NH3 → CH3CH2NH3+ + Br–
● Good Nucleophiles: Most are negatively charged
● Moderate Nucleophile: Compounds with negative charge
and stabilized by resonance
○ Also contains atoms with lone pairs (Sulfur and
Nitrogen)
● Poor Nucleophile: Have hydrogen-oxygen bonds and no
charges
NATURE OF LEAVING GROUP
● The best leaving groups in this series are the halogens:
○ I–, Br–, Cl–
● Poor leaving groups:
○ OH–, RO–, NH2–
■ Rarely if ever displaced in nucleophilic
substitution reactions

NATURE OF HALOALKANE NATURE OF SOLVENT

● Sn1 Reactions ● Protic Solvent: A solvent that contains an -OH group and
○ Governed by Electronic Factors: Relative stabilities is a hydrogen bond donor
of carbocation intermediates ○ Favors SN1 reactions
○ Relative rates: 3° > 2° > 1° > Methyl ■ The greater the polarity of the solvent, the easier
■ 1° and Methyl almost never react by SN1 it is to form carbocations
■ 2° depends on the solvent ■ Both the carbocation and leaving group can be
● SN2 Reactions solvated

QUEMQUEM, EVGV 3
 TRANS: ALKYL HALIDES

the substitution tertiary carbocations

center
Racemization: The
Inversion
carbocation
Configuration: The
intermediate is
nucleophile attacks
Substitution at a planar, and attack by
the stereocenter
stereocenter the nucleophile
from the side
occurs with equal
opposite the leaving
probability from
group
either side
● Polar Protic Solvents: Hydrogen bond donor
○ Can solvate both the anion and the cation
EXERCISE
components of the SN1 reaction
○ The hydrogen bonds stabilizes the carbocation Predict the product of each reaction and its mechanism
● Aprotic Solvent: A solvent that does not contain an -OH
group and is not a hydrogen bond donor
○ Favors SN2 reactions
○ Although solvents that the top of the table are polar,
formation of carbocations in them is more difficult than
in protic solvents
○ The lone pairs of the solvent stabilize the carbocation 1. Secondary Haloalkane + Methanol using Methanol as a
solvent
○ Methanol is a protic Solvent
○ Will undergo SN1 Reaction
○ Cl substituted by OCH3
○ By-product: Methanol and HCl

2. Primary Haloalkane
○ Will undergo SN2 Reaction
○ Bromine is substituted by Iodine
○ By-product: NaBr

3. Secondary Haloalkane using Acetone as a solvent

○ Acetone is an aprotic solvent
○ Will undergo SN2 Reaction
○ Bromine is substituted by CH3S
○ By-product: NaBr

TYPE OF
SN2 SN1
HALOALKANE
SN1 does not occur
The methyl cation is 4. Secondary Haloalkane using Acetone as a solvent
Methyl CH3X SN2 is favored so unstable that it is ○ Acetone is an aprotic solvent
never observed in ○ Will undergo SN2 Reaction
solution ○ Bromine is substituted by SH
SN1 does not occur ○ By-product: NaBr
Primary
carbocations are so
Primary RCH2X SN2 is favored
unstable that they
are not observed in
solution
SN2 is favored in SN1 is favored in
Secondary R2CHX aprotic solvents with protic solvents with 5. Secondary Haloalkane using Ethanol as a solvent
good nucleophiles poor nucleophiles ○ Ethanol is a protic solvent
○ Will undergo SN1 Reaction
SN2 does not occur SN1 is favored
○ Cl is substituted by CH3COO
Tertiary R3CX because of steric because of the ease
○ By-product: NaCl
hindrance around of formation of

QUEMQUEM, EVGV 4
 TRANS: ALKYL HALIDES

11. Primary Haloalkane

○ Will undergo SN2 Reaction
○ Cl is cleaved

6. Secondary Haloalkane using acetone as solvent

○ Acetone is an aprotic solvent
○ Will undergo SN2 Reaction
○ Iodine is substituted by CH3CH2S
○ By-product: NaI

12. Primary Haloalkane

○ Will undergo SN2 Reactions
7. Primary Haloalkane ○ Cl is cleaved
○ Will undergo SN2 Reaction ○ NH3 Nucleophile Attaches
○ Br is substituted by I
○ By-product: NaBr Select which member of each pair shows faster SN2 reaction

8. Methyl Haloalkane
○ Will undergo SN2 Reaction 1. The first one is faster because it is a primary haloalkane
○ Another CH3 would be added to (CH3)3N to form compared to the secondary haloalkane
(CH3)4N

2. The first one is faster because it is a secondary

haloalkane compared to the tertiary haloalkane

9. Primary Haloalkane
○ Will undergo SN2 Reaction
○ Br will be substituted by CH3O
○ By-product: NaBr 3. The first one is faster because it is a secondary
haloalkane compared to the tertiary haloalkane

β- ELIMINATION
● β-Elimination: Removal of atoms or groups of atoms from
adjacent carbons to form a carbon-carbon double bond
○ When a halogen is cleaved there is also a
corresponding hydrogen eliminated
○ Dehydrohalogenation: Type of β-Elimination
■ Elimination of HX
10. Secondary Haloalkane using Ethanol as solvent ■ Elimination of hydrogen and halogen
○ Ethanol is a protic solvent ○ Happens in the presence of a base
○ Will undergo SN1 Reaction
○ Cl is substituted by CH3S
○ By-product: NaCl

● Zaitsev’s Rule: The major product of a β-elimination is the

more stable (the more highly substituted) alkene
○ When cis-trans isomerism is possible, the trans
isomer is favored

QUEMQUEM, EVGV 5
 TRANS: ALKYL HALIDES

SUMMARY OF E1 AND E2

HALOALKANE E1 E2
E1 does not occur.
Primary
carbocations are so
Primary RCH2X E2 is favored
unstable that they
are never observed
in solution
Main reaction with Main reaction with
Secondary R2CHX weak bases such as strong bases such
H2O and ROH as OH– and OR–
Main reaction with Main reaction with
● Two limiting mechanisms for β-elimination reactions: Tertiary R3CX weak bases such as strong bases such
○ E1 Mechanism H2O and ROH as OH– and OR–
○ E2 Mechanism ● Most strong bases are negatively charged ions

E1 MECHANISM SUBSTITUTION VS. ELIMINATION

● E1 Mechanism: At one extreme, breaking of the C-X
bond is complete before reaction with base breaks the
C-H bond
○ Only R-X is involved in the rate-determining step
E1 MECHANISM PROCESS
● Step 1: Break a bond go give a stable molecule or ion
○ Rate-determining ionization of C-X gives
carbocation intermediate and halide ion
○ Breaking of the halogen bond
● Because many nucleophiles are also strong bases (OH–
and RO–), SN and E reactions often compete
● The ratio of SN/E products depends on the relative rates of
the two reactions
○ Mostly happens in secondary haloalkanes
a

SN1 VS E1
● Reaction of 2° and 3° haloalkanes in polar protic
solvents give mixtures of substitution and elimination
products
○ Product ratios are difficult to predict

● Step 2: Take a proton away.

○ Proton transfer from the carbocation to a base (in this
case, the solvent) gives the alkene
○ Breaking of Hydrogen bond for the hormation of
double bond

E2 MECHANISM SN2 VS E2
● E2 Mechanism: At the other extreme, breaking the C-X ● It is considerably easier to predict the ratio of SN2 to E2
and C-H bonds is concerted product
○ Both R-X and base are involved in the
rate-determining step

E2 MECHANISM PROCESS
● One Step Mechanism: All bond-breaking and
bond-forming steps are concerted
○ Occurs simultaneously:
■ Take a proton away
■ Break a bond to form a stable ion or molecule
○ The solvent attracts the hydrogen causing a breakage
of the carbon-hydrogen bond SUBSTITUTION VS ELIMINATION GUIDELINES
● The strength of a nucleophile will dictate the order of a
reaction
○ Strong nucleophiles will react more quickly

QUEMQUEM, EVGV 6
 TRANS: ALKYL HALIDES

● Primary halides usually undergo SN2 with good around the 3°

nucleophiles carbon
● Tertiary halides usually do not undergo SN2 reactions Main reaction with
○ More likely to undergo E2 with a good base, or E1 E2 strong bases (e.g.,
and SN1 otherwise HO– and RO–)
● Secondary halides can react in all ways Main reactions with
○ Hard to predict poor
● The nucleophile will usually favor one or the other type of SN1/E1
nucleophile/weak
reaction bases
○ t- butoxide favors elimination
○ Br– and I– favor substitution
EXERCISE
HALIDE REACTION COMMENTS
Predict the major product and the mechanism for each reaction
The only substitution
Methyl SN2
reactions observed
SN1 reaction of
methyl halides are
never observed
CH3X SN1 1. Tertiary Haloalkane + OH solvent in High Temperature in
The methyl cation is
so unstable that it is the presence of water
never formed in ○ High Temperature favors Elimination Reaction
solution ○ OH Strong base causes E2 Reaction
The main reaction
with strong bases
such as OH– and
EtO–
SN2
Also, the main
reaction with good
nucleophiles/weak
bases (e.g., I– and
CH3COO–)
The main reaction
Primary RCH2X with strong, bulky
E2 bases (e.g.,
potassium 2. Primary haloalkane in the presence of DCM
tert-butoxide) ○ DCM (CH2Cl2) is not a bulky base so SN2 Reaction
Primary cations are would occur
never formed in
solution
SN1/E1
SN1 and E1
reactions of primary
halides are never
observes
The main reaction
with weak
SN2 bases/good
nucleophiles (e.g., I–
and CH3COO–) 3. Secondary haloalkane in the presence of methanol with a
The main reaction strong nucleophile
with strong bases / ○ Methanol is a protic solvent
E2 good nucleophiles ■ Also a weak base
Secondary R2CHX ○ Will undergo SN2 Reaction
(e.g., OH– and
CH3CH2O–)
Common in reaction
with weak
nucleophiles in polar
SN1/E1
protic solvents (e.g.,
water, methanol,
4. Secondary Haloalkane + Strong Nucleophile + Strong
ethanol.)
Base (Acetone)
SN2 reactions of ○ Will undergo E2 reaction
tertiary halides are
Tertiary R3CX SN2 never observed
because of the
extreme crowding

QUEMQUEM, EVGV 7
 TRANS: ALKYL HALIDES

REFERENCES

Notes from the discussion of Sir M. K. Devanadera

University of Santo Tomas Powerpoint Unit 09 Alkyl Halides

QUEMQUEM, EVGV 8
 [TRANS] LEC UNIT 11: ALCOHOLS, ETHERS, AND THIOLS

● Glycerol serves as the backbone for Triacyl glycerides

OUTLINE o Hydroxyl group serves as attachment sites for fatty
I Structures of Alcohols, Ethers, and Thiols acids
II Reactions of Alcohols, Ethers, and Thiols o Creates fatty acid esters
A Acid-Catalyzed Dehydration (Elimination)
B Oxidation
C Thiol Acidity PHYSICAL PROPERTIES OF ALCOHOLS
D Ether Synthesis (SN2)
III Applications BOILING POINT AND SOLUBILITY
● Alkanes are more volatile than alcohols
o Alcohols have higher boiling points
STRUCTURES OF ALCOHOLS, ETHERS, AND THIOLS ● Alkanes are insoluble while short chain alcohols are
soluble
ALCOHOLS o As the chain lengthens, alcohols become insoluble in
water
NOMENCLATURE OF ALCOHOLS
● Alcohol Functional Group: Hydroxyl Group (OH) Boiling Points and Solubility of Alcohols and alkanes of Similar
● Add suffix -ol at the end of the parent chain Molecular Weight
o Ex: 2 Carbon (Ethane) = Ethanol STRUCTURAL
NAME
MOL. BOILING SOL. IN
FORMULA WEIGHT POINT WATER
CH3OH Methanol 32 65 Infinite
CH3CH3 Ethane 30 -89 Insoluble
CH3CH2OH Ethanol 46 78 Infinite
CH3CH2CH3 Propane 44 -42 Insoluble
CH3CH2CH2OH 1-Propanol 60 97 Infinite
CH3CH2CH2CH3 Butane 58 0 Insoluble
CH3CH2CH2CH2OH 1-Butanol 74 117 8 g/100 g
CH3CH2CH2CH2CH3 Pentane 72 36 Insoluble

ACIDITY OF ALCOHOLS
● Alcohols have about the same pKa values as water
● Aqueous solutions of alcohols have the same pH as that
of pure water
o Alcohols and phenols both contain an OH group
o Phenols are weak acids and react with NaOH and
other strong bases to form water-soluble salts
▪ The water -soluble salts are strong bases
▪ Alcohols are weaker acids than phenols and do
not react in this manner
Examples of Alcohols

● Glycols: Compounds containing two hydroxyl groups on

adjacent carbons
o Polyhydroxy functional groups usually use common
names in the laboratory

Reaction of Phenol and Sodium Hydroxide to Produce Sodium

Phenoxide

ETHERS
● Ether Functional Group: Oxygen atom bonded to two
carbon atoms
o In between Carbon Chains
o Simplest: Dimethyl Ether
▪ Two methyl groups attached to oxygen
o Most common: Diethyl Ether
Examples of Glycols ▪ Two ethyl groups attached to oxygen
▪ Commonly used as solvents

QUEMQUEM, EVGV 1
 LEC TRANS: ALCOHOLS, ETHERS, AND THIOLS

o Bonded Carbons: Partial positive charge

▪ Oxygen easily binds to positive carbons

Examples of Ethers

NOMENCLATURE OF ETHERS
● Although ethers can be named by the IUPAC system, Polarity of Ethers
chemists almost invariably use common names for
low-molecular-weight ethers BOILING POINT OF ETHERS
o Common names are derived by listing the alkyl ● Only weak forces of attraction exists between ether
groups bonded to oxygen in alphabetical order and molecules in pure liquid
adding the word “ether” o Boiling points are close to hydrocarbons of similar
o Alternatively, name one of the groups on oxygen as molecular weight
an alkoxy group o Ethers have lower boiling points than alcohols of
▪ IUPAC naming: “Alkoxy Alkane” same molecular formula
▪ Alkoxy: Shorter carbon chain; Alkane: Longer ▪ Ether boiling points are more comparable to
Carbon chain alkanes than alcohols
▪ The difference in boiling points is due to the
position of the oxygen

Comparison Between Ether and Alcohol Boiling Points

Common and IUPAC Nomenclature of Ethers
REACTIONS OF ETHERS
● Cyclic Ether: An ether in which one of the atoms in a ring ● Ethers resemble hydrocarbons in their resistance to
is oxygen chemical reactions.
o A kind of heterocyclic chain o Do not react with oxidizing agents (e.g., Potassium
▪ Heterocyclic Chain: Atoms other than carbons Dichromate)
present within the chain ▪ Do not oxidize because they are already
▪ Homocyclic Chain: Only carbons comprise the stabilized
chain o Do not react with reducing agents (e.g., H2) in
o Also known by their common names transition metal catalysts or with hydride reducing
▪ Ethylene Oxide: Simplest agents (e.g., NaBH4)
▪ Tetrahydrofuran o Not affected by most acids or bases at moderate
o Ethylene Oxide: Important building block for the temperature
organic chemical industry ● Ethers are excellent solvents to carry out organic reactions
▪ Fumigant in food stuffs and textiles o Due to their general inertness and good solvent
properties
▪ Sterilize hospital equipment
▪ They are already stable
o Tetrahydrofuran (THF): Useful laboratory and o Ex: THF and Diethyl ether
industrial solvent
▪ Most common solvent used in chemical reactions THIOLS
● Thiol: Compound containing an Sulfydryl Group (– SH)
o Similar to Alcohol Structure
▪ Oxygen is replaced by Fulfur
o Most outstanding property of low-molecular-weight
thiols: Stench
▪ Responsible for foul smells (e.g., rotten eggs and
sewage)
o The scent of skunks is due primarily to two thiols:
Cyclic Ethers
▪ 2-Butene-1-thiol
PHYSICAL PROPERTIES OF ETHERS ▪ 3-Methyl-1-butanethiol

POLARITY
● Ethers are polar molecules
o Oxygen: Partial negative charge

QUEMQUEM, EVGV 2
 LEC TRANS: ALCOHOLS, ETHERS, AND THIOLS

Examples of Thiols

NOMENCLATURE OF THIOLS Dehydration Reaction of 2-Methyl-2-butanol

● IUPAC names are derived in the same manner as the
names of alcohols
o To show that it is a thiol, the final -e of the parent
alkane is retained and the suffix -thiol is added
● Common names for simple thiols are derived by naming
the alkyl group bonded to -SH and adding “mercaptan”

Nomenclature of Thiols

PHYSICAL PROPERTIES OF THIOLS

POLARITY
● There is a small difference in electronegativity between Other Examples of Dehydration Reactions
sulfur and hydrogen
o 2.5 – 2.1 = 0.4 ● When isomeric alkenes are obtained, the alkene having
o S-H bond is nonpolar covalent the greater number of alkyl groups on the double bond
generally predominates
▪ Thiol (-SH) is Nonpolar
▪ Alcohol is (-OH) Polar

BOILING POINT AND SOLUBILITY

● Thiols show little association by hydrogen bonding
o Have lower boiling points than alcohols
o Less soluble in water than alcohols

Comparing Boiling Points of Thiols and Alcohols

BOILING BOILING
THIOL ALCOHOL
POINT (C) POINT (C)
Examples of Dehydration Reactions where a Product Predominates
Methanethiol 6 Methanol 65
Ethanethiol 35 Ethanol 78
1-Butanethiol 98 1-Butanol 117
OXIDATION
● Oxidation:
o ↑O only
REACTIONS OF ALCOHOLS, ETHERS, AND THIOLS
o ↓H only
ACID-CATALYZED DEHYDRATION (ELIMINATION) o ↑O and ↓H
● Dehydration: Elimination of a molecule of water from
adjacent carbon atoms gives an alkene OXIDATION OF ALCOHOLS
o Water is eliminated ● Oxidation of a 1o alcohol gives an aldehyde or a
▪ OH functional group + Hydrogen from an carboxylic acid depending on experimental conditions
α-carbon = H2O o Carboxylic acid is produced using potassium
▪ A hydrogen atom is also removed from an dichromate (K2Cr2O7) in aqueous sulfuric acid
▪ Chromic Acid Test
adjacent carbon with OH to stabilize the carbon
o Either Complete or Partial Oxidation
o Most often brought about by heating an alcohol with
o Usually:
either:
▪ 85% H3PO4 ▪ Alcohol → Aldehyde → Carboxylic Acids
▪ Concentrated H2SO4
o Major product would be the one with the most
substituent
▪ Major Product: Alkene
▪ By-Product: Water Oxidation Reactions of Primary Alcohol

QUEMQUEM, EVGV 3
 LEC TRANS: ALCOHOLS, ETHERS, AND THIOLS

● Oxidation of a 2o alcohol gives a ketone o The partial negative charge of oxygen attracts the
partial positive carbon of the alkyl in the alkyl halide
▪ Halogen is cleaved; Na is cleaved
▪ Cleaved Halogen binds with Na
o Forms:
▪ Major Product: Ether
▪ By-product: Salt

Oxidation of a Secondary Acid Using Chromic Acid

● 3o alcohols are resistant to oxidation

o In the presence of an acid-catalyst they are prone to
dehydration Ether Synthesis Reaction of Cyclopentanol
o Only undergoes elimination reactions
EXERCISE
Predict the major product of the following reactions:

1.

Tertiary Alcohols Do Not Oxidize

OXIDATION OF THIOLS ● Alcohol (2-Methylcyclohexan-1-ol) is heated in the

presence of concentrated H2SO4 (Sulfuric Acid)
● Most common reactions of thiols in biological systems is
o Undergoes Dehydration Reaction
their oxidation to disulfides
o Forms a disulfide bridge between two thiols o Major Product: 1-Methylcyclohex-1-ene
o By-Product: Water
▪ Disulfide functional group: Disulfide (-S-S-) Bond
o Thiols are readily oxidized to disulfides by O2
2.
o Disulfides are easily reduced to thiols by reducing
agents (H2) in the presence of a transition metal
catalyst

● Secondary Alcohol (Cyclohexanol) is reacted with

Potassium Dichromate (K2Cr2O7) in the presence of H2SO4
Oxidation of Thiols (Creates Chromic Acid)
o Undergoes oxidation to produce a Ketone
THIOL ACIDITY o Major Product: Cyclohexanone
● Thiols are weak acids (pKa: 10) and are comparable in
strength to phenols (pKa) 3.
o Thiols react with strong bases (e.g., NaOH) to form
water-soluble thiolate salts
▪ Water-soluble thiolate salts are strong bases

● Secondary Alcohol (3-methylbutan-2-ol) is reacted with

Potassium Dichromate (K2Cr2O7) in the presence of H2SO4
Reaction of a thiol with a strong base to produce a water-soluble (Creates Chromic Acid)
thiolate salt o Undergoes oxidation to produce a Ketone
o Major Product: 3-Methylbutan-2-one
ETHER SYNTHESIS (SN2)
● Williamson Ether Synthesis: Reaction of metal alkoxides 4.
and primary alkyl halides and tosylates in an SN2 reaction
o Best method for the preparation of ethers
● Alkoxides are prepared by reaction of an alcohol with a
strong base (e.g., NaH: Sodium Hydride)
o There is a nucleophilic acyl substitution
● Mechanism of reaction:
o Hydroxyl group reacts with the strong base (NaH) to
● Thiol is reacted in the presence of Oxygen (O2)
produce an alkoxide ions (Presence of Na+ ions)
o Undergoes Oxidation
▪ Creates a partial negative charge on Oxygen
o Major Product: Disulfide bond

QUEMQUEM, EVGV 4
 LEC TRANS: ALCOHOLS, ETHERS, AND THIOLS

APPLICATIONS

IMPORTANT ALCOHOLS

● Propene: Raw material base for the manufacture of

important compounds such as:
o Epoxy glue and resins
o Isopropyl alcohol
o Glycerin, Glycerol

QUEMQUEM, EVGV 5
 [LEC/LAB] UNIT 12: ALDEHYDES AND KETONES
● Formaldehyde, acetaldehyde, and acetone are infinitely
soluble in water
OUTLINE
● Aldehydes and ketones become less soluble in water as
I STRUCTURES OF ALDEHYDES AND KETONES
the hydrocarbon portion of the molecule increases in size
II OXIDATION AND REDUCTION REACTIONS ○ Becomes less soluble in water as the hydrogen
III SYNTHESIS OF ALCOHOLS chain or hydrocarbon chain increases
IV ACETAL/KETAL FORMATION
V KETO-ENOL TAUTOMERISM OXIDATION REACTION
● Aldehydes are oxidized to carboxylic acids by a variety of
oxidizing agents, including potassium dichromate
STRUCTURE OF ALDEHYDES AND KETONES ○ When you have an aldehyde, it can further oxidize
● The functional group of an aldehyde is a carbonyl group to form an acid in the presence of potassium
bonded to a hydrogen atom dichromate and sulfuric acid
o In a methanal (formaldehyde), the simplest aldehyde,
the carbonyl group is bonded to two hydrogens
o In other aldehydes, it is bonded to one hydrogen and
one carbon group
● The functional group of a ketone is a carbonyl group
bonded to two carbon groups

● Liquid aldehydes are so sensitive to oxidation by O2 in

the air that they must be protected from contact with air
during storage
○ Protect these aldehydes in atmospheric air that
contains oxygen
○ The presence of oxygen can turn benzaldehyde to
● One requirement for it to become an aldehyde is that form a benzoic acid
you have a double bond oxygen with a hydrogen
○ To become a ketone, there should be a C double
bond O

PHYSICAL PROPERTIES
● Ether and alkane has a similar molecule weight, and
somehow similar boiling point
● Having an aldehyde as a functional group increases the
boiling point
● Butanal and butanone has the same molecular weight,
different functional group, and slightly different boiling ● Oxidation of aldehydes are different depending on the
points oxidizing agent needed
● Butanol and an acid has a high difference in boiling ● Ketones resist oxidation by most oxidizing agents
points ○ Including potassium dichromate and molecular
oxygen
Table No. 1. ○ To differentiate aldehydes from ketones we use
NAME STRUCTURAL MOLECULAR BOILING Tollens’ test
FORMULA WEIGHT POINT (ºC)
Diethyl CH3CH2OCH2CH3 74 34 ● Tollens’ reagent is specific for the oxidation of aldehydes
ether ○ If done properly, silver deposits on the walls of the
container as silver mirror
Pentane CH3CH2CH2CH2CH3 72 36
Butanal CH3CH2CH2CHO 72 76
2-butanone CH3CH2COCH3 72 80
1-butanol CH3CH2CH2CH2OH 74 117
Propanoic CH3CH2COOH 74 141
acid
● Silver ammonia is the Tollens’ reagent.

SURNAMES (ALL CAPS) | 1AMT 1

 TRANS: ALDEHYDES AND KETONES

● The presence of aldehyde it forms a carboxylic anion, ● In the synthesis of alcohol, first step is to prepare the
and a silver (a precipitate), ammonia, and water Grignard reagent
● If you have ketone, it will be negative in Tollens’ test

REDUCTION REACTION
● The carbonyl group of an aldehyde or ketone is reduced
to an -CHOH group by hydrogen in the presence of a
transition metal catalyst
○ Reduction of an aldehyde gives a primary alcohol
○ Reduction a ketone gives a secondary alcohol

FOR EXAMPLE:

CH3Cl + Mg → (in the presence of Ether) CH3MgCl

● Longer chain of alkyl is allowed

● The synthesis below are examples A N reaction

○ In the synthesis of alcohol, the mechanism of action
is called nucleophilic addition
○ The nucleophilic addition in the example is
because of the water molecule
■ The nucleophile in water is because of the lone
pair present in the oxygen
EXAMPLE:

● Hydride ion is attracted to a partially positive carbon so

that the double bond between C = O will become a lone
pair in the oxygen giving it a negative charge, forming an
alkoxide ion
● In the presence of an acid, hydrogen in the proton is
interacting with the oxygen and the hydrogen (blue) will
be cleaved, which forms alcohol

Figure No. 1. Synthesis of Alcohol

● If you want to produce a primary alcohol you need to

● Reduction by NaBH4 does not affect a carbon-carbon
double bond or an aromatic ring
○ If you have Cinnamaldehyde, and interact it with
NaBH4 and H2O, it will give you Cinnamyl alcohol
○ It does not react with the double bonds or the
benzene ring
○ It will just interact with the aldehyde functional group
have methanal
○ Methanal reacting with RMgX to produce
RCH2OMgX will be the complex between the
methanal and the Grignard reagent.
○ After that, you have water, with which the lone pair
present in the oxygen of water will be attracted to the
partially positive carbon in RCH2OMgX
○ After that OMgX will be cleaved, and the hydrogen in
water will also be cleaved to produce Mg(OH)X and
the primary alcohol

In the primary alcohol 1º, your alkyl group in the RMgX

SYNTHESIS OF ALCOHOLS
● The synthesis of alcohols involve using a Grignard
reagent
○ Uses Grignard reagent – produced by mixing alkyl
halide with magnesium in the presence of an ether
as the solvent, to produce Grignard reagent (R Mg
X)
(Grignard reagent) is the chain that will bind to your
methanal.
● In the structure CH2OH, the CH2 comes from the
methanal
● OH comes from the nucleophile (H2O)
● R group comes from the Grignard reagent
!! If you want to prepare a primary alcohol, you need
methanal
!! if you want to elongate the chain of primary alcohol,
you need to alter the Grignard reagent

SURNAMES | 1AMT 2
 TRANS: ALDEHYDES AND KETONES

EXAMPLE:

1. In the laboratory, you are asked to produce a 1-hexanal

● You need methanal to produce the primary alcohol
○ In that case, the Alkyl halide should be
CH3CH2CH2CH2CH2MgCl and it should react
with methanal to form 1-hexanal
● If you want to produce a secondary alcohol you
If you have a 4-hydroxypentanal
need an aldehyde that has an R group and your
● Cyclic hemiacetal can be formed
Grignard reagent
● There is a formation of cyclic
○ The length of your carbon chain will be based
● Lone pair of oxygen in O – H is attracted to the carbon
on the R group of your Grignard reagent and
in C = O, which will result to binding
your aldehyde
● The double bond between C = O will become a lone
● In terms of tertiary alcohol, the length of the carbon
pair with which the hydrogen atom in O – H will be
chain will depend on the Grignard reagent and the
attracted
ketone

FORMATION OF ACETAL
SUMMARY: ● 2 moles of alcohol + Aldehyde
● Primary alcohol – methanal ● A hemiacetal can react further with an alcohol to form an
● Secondary alcohol – aldehydes (ethanal and above) acetal plus water
● Tertiary alcohol – ketone ● This reaction is acid catalyzed
● The addition of an alcohol to a hemiacetal is a
nucleophilic addition AND elimination (A NE)
ADDITION OF ALCOHOLS
FORMATION OF HEMIACETAL
● Aldehyde + Alcohol
● Addition of a molecule of alcohol to the carbonyl group of
an aldehyde or ketone forms a hemiacetal (a half-acetal)
○ Hemi means half
○ If we add alcohol on aldehyde, we are forming
hemiacetal and acetal
○ If we add alcohol to ketone, we are forming
hemiketal and ketal
● This is also an example of a nucleophilic addition
reaction (AN)
○ Because we are adding an alcohol
● Once you have a hemiacetal, you need another mole of
alcohol to form an acetal
○ The lone pair in oxygen is attracted to the partially
positive charge of the carbon which allows the
formation of acetal

The formation of hemiacetal, acetal, hemiketal, and ketal

● If we react benzaldehyde with ethanol, the oxygen’s
lone pair is attracted to the partially positive carbon
● The carbon will become unstable and the double bond
will be transmitted to the oxygen and will have a
negative charge due to the excess lone pair
● If the oxygen binds with the carbon, it will give off the
hydrogen
● The hydrogen will interact with the negatively charged
oxygen forming A-hemiacetal
● When a hydroxyl group is part of the same molecule that
contains the carbonyl group and a five- or six- membered
ring can form, the compound exists almost entirely in a
cyclic hemiacetal form
formation is important in biochemistry
● Because it involves different chemical reactions
specifically in the sugar reaction in general
biochemistry
● Hemiacetal has a C single bond OH, and C single bond
O with an R group
● Acetal’s structure, compared to hemiacetal, has its O-H
replaced with an alkyl group
MECHANISM OF ACETAL FORMATION
Step 1. Add a proton. Adding a proton to the carbonyl oxygen
makes the carbonyl carbon a stronger electrophile and more
susceptible to attack by a nucleophile.

SURNAMES | 1AMT 3
 TRANS: ALDEHYDES AND KETONES
Step 2. Reaction of an electrophile and a nucleophile to form a
new covalent bond.
● This step adds the first –– OR group required for acetal
formation. The intermediate form is an oxonium ion.
Step 3. Protons transfer to another oxygen. The proton
transferred is in red.
Step 4. Break a bond to form stable molecules for ions. In
this case the stable molecule is H2O and the stable ion is a 3º
carbocation.
Step 5. Reaction of an electrophile and a nucleophile to
form a new covalent bond. This step adds the second –OR
group of the acetal to what was the original carbonyl carbon.
Step 6. Take a proton away. Transfer of a proton to solvent
gives the acetal and regenerates the H+ catalyst.
SURNAMES | 1AMT
SUMMARY:
● You have aldehyde with 1 mol alcohol to form hemiacetal
(nucleophilic addition)
● Proceed to form acetal and will need another mole of
alcohol
○ Elimination reaction which eliminates the hydrogen
● If you use ketone with another alcohol, you are formine
hemiketal
● If you react it with another mole of alcohol, you will form a
ketal group
DIFFERENCE OF HEMIKETAL WITH HEMIACETAL
● The presence of hydrogen in the structure
● Hemiacetal/Acetal – If hydrogen is bonded to the
central carbon
● Hemiketal/Ketal – if hydrogen is in the form of alkyl
group
SUMMARY
Figure No. 2. Table of Reactions with Amines and its
Derivatives
KETO-ENOL TAUTOMERISM
● A carbon atom adjacent to a carbonyl group is called an
a-carbon, and a hydrogen atom bonded to it is called an
a-hydrogen.
○ The ones that are binded to the carbonyl carbon
● There is a transfer of double bonds between C = O to the
neighboring carbon to form a double bond
○ Once the double bond is formed, the hydrogen
transfers to the oxygen
○ Oxygen will become negatively charged
● From the name itself, from KETONE it is forming a double
bond (EN), and alcohol which is OL
● It is in equilibrium
○ Acetone can form a keto-enol form
4
 TRANS: ALDEHYDES AND KETONES

REFERENCES

Notes from the discussion of [Insert prof here]

University of Santo Tomas Powerpoint [Insert subject]

[Insert book and page number if applicable]

● An aldehyde or ketone that has a hydrogen on an

a-carbon is in equilibrium with a constitutional isomer
called an enol.
○ The name “enol” is derived from the IUPAC
designation of it as both an alkene (-en-) and an
alcohol (-ol).
○ In a keto-enol equilibrium, the keto form generally
predominates.

KETO-ENOL TAUTOMERISM
● Example 17-8: Draw structural formulas for the two enol
forms for each ketone

SOLUTION:

SURNAMES | 1AMT 5
 [LEC] UNIT 13: CARBOXYLIC ACIDS AND ITS DERIVATIVES

OUTLINE

1.1 Structures of Carboxylic Acids

1.2. Fischer Esterification
1.3 Decarboxylation
1.4 Structures of Carboxylic Acid Derivatives
1.6 Preparation of Carboxylic Acid Derivatives (S NAcyl)
1.7 Hydrolysis of Carboxylic Acid Derivatives FISCHER ESTERIFICATION
1.8 Reactions with Alcohols and Amines Fisher esterification is one of the most commonly used
1.9 Phosphoric Derivatives methods for the preparation of esters.

● Esters are one of the important industrial molecules

CARBOXYLIC ACIDS that is used in different products

● In this chapter, we study carboxylic acids, another class of ● In Fischer esterification, a carboxylic acid is reacted
organic compounds containing the carbonyl group. with an alcohol in the presence of an acid catalyst,
most commonly concentrated sulfuric acid.
● The functional group of a carboxylic acid is a carboxyl
group, which can be represented in any one of three
ways. (contains a carbonyl functional group and hydroxyl
functional group)

In this example, the lone pairs of the oxygen of ethanol is

attracted to the partially charged carbon of the ethanoic acid.
NOMENCLATURE - TABLE 18-1 Hence, forming of a covalent bond (tetrahidral carbon). After
that, the double bond in the carbonyl group transfers to its
oxygen molecule to create lone pairs and make it negatively
charged. Since the negative oxygen is not happy, it will return
the lone pair to carbon, forming a double bond again.
Consequently, the carbon is unstable so it cleaves the hydroxyl
group.The hydrogen from the ethanol is also cleaved to revert
back the bond its oxygen and remove its positive charge. The
cleaved out hydroxyl and hydrogen then reacts together
forming the by-product, water.

● In naming ester, we name alcohol as the substituent

and the carboxylic group becomes the parent chain
(oic acid is replaced bt oate)
● Fischer esterification is reversible.
● In Fischer esterification, the alcohol adds to the
carbonyl group of the carboxylic acid to form a
tetrahedral carbonyl addition intermediate.
● The intermediate then loses H2O to give an ester.
Nomenclature
For common names, use, the Greek letters alpha (a), beta (β),
gamma (ℽ), and so forth to locate substituents.

● Carbon beside the functional group is the alpha carbon,

then bata, and the gamma.

SURNAMES (ALL CAPS) | 1AMT 1

 TRANS: TOPIC (ALL CAPS)

CARBOXYL DERIVATIVES
In this chapter, we study three classes of compounds derived
from carboxylic acids; anhydrides, esters, and amides, acyl
halides.
● Each is related to a carboxyl group by loss of H2O.
● Carboxylic acid reacts with another carboxylic acid to
form anhydride. A cyclic amide is called a lactam (heterocyclic compound).
● Can be in terms of ammonia, primary amine, or
secondary amine
● Acyl halide forms when you react carboxylic acid with
HX or any halide containing acid.
● All reaction involves nucleophilic acyl substitution

● The penicillins are referred to as b-lactam

antibiotics.

ANHYDRIDES
The functional group of an anhydride is two carbonyl groups
bonded to the same oxygen.
● The anhydride may be symmetrical (from two identical
acyl groups), or mixed or asymmetrical (from two
different acyl groups). ● The cephalosporins are also b-lactam antibiotics.
● To name an anhydride, drop the word “acid” from the
name of the carboxylic acid from which the anhydride
is derived and add the word “anhydride.”
● Alphabetical order (ex. Ethanoic acid and butanoic
acid, butanoic acid will come first)

ESTERS
The functional group of an ester is a carbonyl group bonded to
Some Preparation Reactions
an -OR group. R may be alkyl or aryl.
● Both IUPAC and common names of esters are
derived from the names of the parent carboxylic
acids.
● Name the alkyl or aryl group bonded to oxygen first,
followed by the name of the acid; replace the suffix -ic
acid by -ate
● A cyclic ester is called a lactone.

● Y - denoted the leaving group because it is removed

during the nucleophilic substitution
AMIDES ● Hydrolysis - formation of acid
The functional group of an amide is a carbonyl group bonded ● Alcoholysis - formation of ester and by-product HY
to a nitrogen atom. ● Aminolysis - formation of amide and by-product HY
● To name an amide, drop the suffix -oic acid from the ● Reduction - formation of aldehyde which with further
IUPAC name of the parent acid, or -ic acid from its reduction forms an alcohol
common name, and add -amide. ● Grignard reaction - formation of ketone that when
● If the amide nitrogen is also bonded to an alkyl or aryl reacted with R’MgX produces a tertiary alcohol
group, name the group and show its location on
nitrogen by N- ; two alkyl or aryl groups by N, N-di-. HYDROLYSIS OF ANHYDRIDES
Hydrolysis is a chemical decomposition involving breaking a
bond and the addition of the elements of water.

SURNAMES (ALL CAPS) | 1AMT 2

 TRANS: TOPIC (ALL CAPS)

● Carboxylic anhydrides, particularly the ALCOHOLYSIS

low-molecular-weight ones, react readily with water
(hydrolyze) to give two carboxylic acids.
● Symmetric forms 2 acids of the same kind
● Asymmetric forms 2 kinds of acid
● No need for a catalyst
Anhydrides react with alcohols and phenols to give an ester
and a carboxylic acid.
● Reacting alcohol with an acid derivative/ acid to form
another acid derivative

Aspirin is prepared by the reaction of salicylic acid with acetic

anhydride.

HYDROLYSIS OF ESTERS
● Esters hydrolyze only very slowly, even in boiling water.
● Acid as the catalyst
● Hydrolysis becomes considerably more rapid, however,
when the ester is heated in aqueous acid or base.
● Hydrolysis of esters in aqueous acid is the reverse of
Fischer esterification.
● A large excess of water drives the equilibrium to the right AMINOLYSIS
to form the carboxylic acid and alcohol (Le Châtelier's
principle). Anhydrides react with ammonia and with 1° and 2° amines to
● For Hydrolysis of Acyl Halides form amides.
- We just need water ● Two moles of amine are required; one to form the
- No need for a catalyst amide and one to neutralize the carboxylic acid
- Produce an acid and halide by-product.
● Forms amide and ammonium salt

● We can also hydrolyze an ester using a hot aqueous base,

such as aqueous NaOH.
● This reaction is often called saponification, a reference to
its use in the manufacture of soaps.
● The carboxylic acid formed in the hydrolysis reacts with
hydroxide ion to form a carboxylic acid anion.
● Each mole of ester hydrolyzed requires one mole of base.

● Esters react with ammonia and with 1° and 2° amines

to form amides.
● Forms amide and an alcohol

HYDROLYSIS OF AMIDES
Amides require more vigorous conditions for hydrolysis in both
acid and base than do esters.
● Acid and heat is needed
● Hydrolysis in hot aqueous acid gives a carboxylic acid ● Thus, an amide can be prepared from a carboxylic
and an ammonium ion. acid by first converting the carboxylic acid to an ester
● Hydrolysis is driven to completion by the acid-base by Fischer esterification and then reaction of the ester
reaction between ammonia and/or the amine and the with an amine.
acid to form an ammonium ion. ● Amides do not react with ammonia or with amines
● Each mole of amide hydrolyzed requires one mole of
acid.

REFERENCES

Notes from the discussion of [Insert prof here]

University of Santo Tomas Powerpoint [Insert subject]

● Hydrolysis of an amide in an aqueous base gives a
carboxylic acid salt and ammonia or an amine. [Insert book and page number if applicable]
● Hydrolysis is driven to completion by the acid-base
reaction between the carboxylic acid and base to form a
salt.
● Each mole of amide hydrolyzed requires one mole of
base.

SURNAMES (ALL CAPS) | 1AMT 3

 [LEC] UNIT 14: AMINES
OUTLINE
I STRUCTURE OF AMINES
II BASICITY OF AMINES
III REACTIONS OF AMINES
A Nucleophilic Substitution
B β-Elimination
STRUCTURE AND CLASSIFICATION
● Amines are classified as 1°, 2°, 3° depending on the
number of carbon groups bonded to nitrogen
o Just like thiol, alcohol, amide it can form 1°, 2°, 3°
alcohol, depends on how many substituent or how
many carbon substituent are bonded to the nitrogen
● Aliphatic amine: all carbons bonded to nitrogen are
derived from alkyl groups. See the three above
o Wherein you have aliphatic carbons bonded to the
amine
o It can by acyclic (linear) or cyclic
● Aromatic amine: one or more of the groups bonded to
nitrogen are aryl groups
o Wherein the aromatic ring is bonded to the nitrogen
● Heterocyclic amine: an amine in which the nitrogen atom
is part of a ring
o Nitrogen is part of the cyclic structure
● Heterocyclic aliphatic amine: a heterocyclic amine in
which the ring is saturated (has no C=C bonds)
o The cyclic is not aromatic
● Heterocyclic aromatic amine: the amine nitrogen is part
of an aromatic ring
o Nitrogen is part of aromatic ring
PHYSICAL PROPERTIES
● Like ammonia, low-molecular-weight amines have very
sharp, penetrating odors
○ Trimethylamine, for example, is the pungent
principle in the smell of rotting fish
SURNAMES (ALL CAPS) | 1AMT
○ Two other particularly pungent amines are
1,4-butanediamine (putrescine) and
1,5-pentanediamine (cadaverine)
■ Two by product of metabolic
reaction in microorganism
■ Most of the amines have a foul
smell
BASICITY OF AMINES
● Like ammonia, amines are weak bases if you are going
to compare it with ionic bases, and aqueous solutions of
amines are basic
○ The acid-base reaction between an amine and
water involves transfer of a proton from water to
the amine
● Methylamine in water it produces a methylammonium
hydroxide which is basic
● Aliphatic amines have about the same base strength
and are slightly stronger bases than NH3
● Aromatic and heterocyclic aromatic amines are
considerably weaker bases than aliphatic amines
● Aromatic amines are weaker than ammonia and aliphatic
that is because of the electron pull done by your aromatic
ring, they do electron pulling making them a weaker base
● Note that while aliphatic amines are weak bases by
comparison with inorganic bases such as NaOH, they are
strong bases among organic compounds.
● Given the basicities of amines, we can determine which
form of an amine exists in body fluids, say blood.
○ In a normal, healthy person, the pH of blood is
approximately 7.40, which is slightly basic
○ If an aliphatic amine is dissolved in blood, it is
present predominantly as its protonated
(conjugated acid) form
■ Protonated can be dissolved in
blood
1
 TRANS: AMINES

REACTION OF AMINES
● The most important chemical property of amines is
their basicity
● Amines, whether soluble or insoluble in water, react
quantitatively with strong acids to form water-soluble
salts.
○ Once they form a salt they can easily be
soluble in water

● Norepinephrine is insoluble in water, but if we add

hydochloric acid it becomes a salt which is a
water-soluble salt
BASICITY OF AMINES (EXAMPLES)
Example 16-5: Complete each acid-base reaction and name
the salt formed

Solution:

REFERENCES

Notes from the discussion of [Insert prof here]

University of Santo Tomas Powerpoint [Insert subject]

[Insert book and page number if applicable]

SURNAMES (ALL CAPS) | 1AMT 2

 TRANS: AMINES

SURNAMES (ALL CAPS) | 1AMT 3