Organic Chemistry
AS Level
WELCOME TO THE CLUB!!
"How many are your works,
Lord! In wisdom you made them
all; the earth is full of your
creatures."
Psalm 104:24:
01
Introduction
ORBITAL INSIDE THE ATOM
ORBITAL
Electrons are arranged around the nucleus in principal energy levels or principal quantum shells
Principal quantum numbers (n) are used to number the energy levels or quantum shells
The lower the principal quantum number, the closer the shell is to the nucleus
So, the first shell which is the closest to the nucleus is n = 1
The higher the principal quantum number, the greater the energy of the shell and the further away
from the nucleus, Each principal quantum number has a fixed number of electrons it can hold
n = 1 : up to 2 electrons
n = 2 : up to 8 electrons
n = 3 : up to 18 electrons
n = 4 : up to 32 electrons
Introduction
The principal quantum shells are split into
subshells which are given the letters s, p and d
Elements with more than 57 electrons also have
an f shell
The energy of the electrons in the subshells
increases in the order s < p < d
AUFBAU
RULES
Electron Configuration of Al :
13e
1s2
2s2 ; 2p6
3s2; 3p1
PAULI
Write electron configurations of :
Tin
Copper
Strontium
Zinc
Rhodium
Carbon
Vanadium
Zirconium
Fluorine
Silver
Organic Chemistry
AS Level
WELCOME TO THE CLUB!!
Elaine Wynette Wijaya
CATHERINE ALICIA FAYE
Grace Abigail Mulia
HANA GRACIA
Park Ji Ho
KEVIN SU
Anastacia Charissa Hartono
LOUISE JOVINCCI
NADIA CHRISTY LI
NILKANTA HARESH DESAI
KENNETH SEBASTIAN LAWRUS
ANGELINA FIDELIA HEHI
Joshua Wilbert Gunawan
Emily Joanna Wu
Gwen Nicoline Emanuele
Karen Maanary
Kyora Adrianne Kristyanto
William Kharismantik
Let’s
introduce
ourself
Name
Dream
Why PSTD?
WHY CHEMISTRY??
Planning
TOTAL : Monday
17x meeting (Jan - May 2025)
Total chapter in syllabus : (2025-2027)
13-21
Jan-Mar
Apr-May
Introduction to Organic Chem
Hydrocarbon
Halogenoalkanes
Alcohol, ester, Carboxylic acid
Carbonyl
Planning
Jan - June 2025 (TP) : Organic Chem AS Level
Jul - Aug 2025 : Finishing
Sept 2025 : past paper
Oct-Nov 2025 : Review + CAIE ON SERIES
Jan-Mar
Apr-May
1x DT
1x DT
3 March 2025
19 May 2025
ORGANIC CHAPTER
13 An introduction to AS Level organic chemistry
14 Hydrocarbons
15 Halogen compounds
16 Hydroxy compounds
17 Carbonyl compounds
18 Carboxylic acids and derivatives
19 Nitrogen compounds
20 Polymerisation
21 Organic synthesis
ORGANIC COMPOUND
FUnctional group :
Naming :
1. Longest chain
2. Determine the functional group
Number the Chain:
●
1.
2.
●
Number the carbon atoms to give the lowest possible numbers to:
1. Functional groups
2. Double/triple bonds
3. Substituents
Add Prefixes for Substituents: di, tri, tetra ….
Functional Group Priority:
The functional group with the highest priority gets the lowest number. Priority order (highest to lowest):
1. Carboxylic acid (-COOH)
2. Aldehyde (-CHO)
3. Ketone (-C=O)
4. Alcohol (-OH)
5. Amines (-NH₂)
6. Alkenes (-C=C-) and alkynes (-C≡C-)
Practice
Naming quiz 3.pdf
Naming Quiz 4.pdf
Naming Quiz 9.pdf
Practice : (Skeletal)
1.
2.
3.
CH3(CH2)3OH
(CH3)2CHCH2OH
CH3CH2OCH2CH3
Draw The skeletal formula
Drawing
Bonding in Organic Molecules
Single covalent bond : Sigma bond (σ) (SP3)
Double covalent bond : Phi bond (π), One sigma bond (σ) → SP2
Triple bond : 2 Phi bond (π), One sigma bond (σ) → SP
Practice 14.4
13-3-shapes-of-organic-molecules--and--bonds-HXsdrPNsmRbsZZcy.pdf
Isomer
ISO : same
Straight Chain
Branched Chain
Cyclic Chain
Structural isomer : Same MF, diff SF
Chain isomer : Same MF, diff longest chain
Positional : position of functional group
Functional : same MF, diff functional group
ETER :
Smaller chain : -Oxy
Main chain : Alkane
Functional Group Isomer
Practice 14.5
Stereoisomer :
Stereoisomers are compounds that have the same atoms connected to each
other, however the atoms are differently arranged in space
E/Z nomenclature is used to distinguish between the isomers
You may see this type of isomerism referred to in other sources as cis/trans
isomerism, This is a special case of E/Z isomerism
A "cis" isomer would essentially be the same as a "Z" isomer (The Z comes from the
German word "zusammen" meaning together)
a "trans" isomer would also essentially be the same as an "E" isomer (The E comes
from the German word "entgegen" meaning opposite)
CIS vs Trans
●
Cis/trans nomenclature is used to distinguish between
the isomers
○ Cis isomers have functional groups on the
same side of the double bond/carbon ring
○ Trans isomers have functional groups on
opposite sides of the double bond/carbon ring
When the groups R1, R2, R3 and R4 are all different (i.e. R1 ≠ R2 ≠ R3 ≠ R4), we have to
use the E / Z naming system, This is based on Cahn-Ingold-Prelog (CIP) priority rules
Guess E/Z
Geometrical
Optical Isomer
Uses in pharmacy, Bio Chem
TYPES of organic reaction :
Homolytic → radical
Heterolytic → uneven
breaking bonds,
depend on their
electronegativity
Electronegativity is a chemical property that
describes the tendency of an atom or a
functional group to attract electrons toward itself.
Differences more
than 1.7 or higher :
ionic bonds
Covalent : between
0.4 - 1.7
Substitution reaction in alkane
Alkene
Alkene produced : (a) elimination of HX from a halogenoalkane by ethanolic NaOH and heat
(b) dehydration of an alcohol, by using a heated catalyst (e.g. Al2O3) or a concentrated acid
(e.g. concentrated H2SO4), (c) cracking of a longer chain alkane
2 describe the following reactions of alkenes:
(a) the electrophilic addition of (i) hydrogen in a hydrogenation reaction, H2(g) and Pt/Ni catalyst and heat
(ii) steam, H2O(g) and H3PO4 catalyst ; (iii) a hydrogen halide, HX(g), at room temperature ; (iv) a halogen, X2
(b) the oxidation by cold dilute acidified KMnO4 to form the diol ; (c) the oxidation by hot concentrated
acidified KMnO4 leading to the rupture of the carbon–carbon double bond and the identities of the
subsequent products to determine the position of alkene linkages in larger molecules
(d) addition polymerisation exemplified by the reactions of ethene and propene
3. describe the use of aqueous bromine to show the presence of a C=C bond
4 describe the mechanism of electrophilic addition in alkenes, using bromine/ethene and
hydrogen bromide/propene as examples
5 describe and explain the inductive effects of alkyl groups on the stability of primary, secondary and
tertiary cations formed during electrophilic addition (this should be used to explain Markovnikov addition)
Mostly alkene
recall the reactions (reagents and conditions) by which halogenoalkanes can be produced:
(a) the free-radical substitution of alkanes by Cl2 or Br2 in the presence of ultraviolet light, as exemplified
by the reactions of ethane ; (b) electrophilic addition of an alkene with a halogen, X2, or hydrogen halide,
HX(g), at room temperature ; (c) substitution of an alcohol, e.g. by reaction with HX(g); or with KCl and
concentrated H2SO4 or concentrated H3PO4; or with PCl3 and heat; or with PCl5; or with SOCl2
2 classify halogenoalkanes into primary, secondary and tertiary
3 describe the following nucleophilic substitution reactions: (a) the reaction with NaOH(aq) and heat to
produce an alcohol; (b) the reaction with KCN in ethanol and heat to produce a nitrile ; (c) the reaction with
NH3 in ethanol heated under pressure to produce an amine ; (d) the reaction with aqueous silver nitrate in
ethanol as a method of identifying the halogen present as exemplified by bromoethane
4 describe the elimination reaction with NaOH in ethanol and heat to produce an alkene as exemplified by
bromoethane
5 describe the SN1 and SN2 mechanisms of nucleophilic substitution in halogenoalkanes including the
inductive effects of alkyl groups
6 recall that primary halogenoalkanes tend to react via the SN2 mechanism; tertiary halogenoalkanes via
the SN1 mechanism; and secondary halogenoalkanes by a mixture of the two, depending on structure
7 describe and explain the different reactivities of halogenoalkanes (with particular reference to the relative
strengths of the C–X bonds as exemplified by the reactions of halogenoalkanes with aqueous silver
nitrates)
Nucleophiles (seeking nucleus) Electrophiles (electron loving) +
Has lone pair electron, Attracted to positive region
(Cl-, Br-, H2O, NH3, CN-, R-NH2
●
●
Attracted to negative charge / electron rich
H+, Br+, Cl+, NO2+, R+
SN1
SN2 Mechanism
Nucleophilic substitution
SN1 ( Substitution Nucleophilic
Unimolecular)
Faster if it has tertiary
halogenoalkanes rather than
primary halogenoalkanes.
RX molecules involve : unimolecular
SN2 ( Substitution Nucleophilic Bimolecular)
One step process, Both RX and nucleophile involved
Dominant in primary halogenoalkanes
Hydroxy (OH-)
alcohols can be produced:
(a) electrophilic addition of steam to an alkene,
H2O(g) and H3PO4 catalyst
(b) reaction of alkenes with cold dilute acidified
potassium manganate(VII) to form a diol
(c) substitution of a halogenoalkane using
NaOH(aq) and heat
(d) reduction of an aldehyde or ketone using
NaBH4 or LiAlH4
(e) reduction of a carboxylic acid using LiAlH4
(f) hydrolysis of an ester using dilute acid or dilute
alkali and heat
2. describe:
(a) the reaction with oxygen (combustion)
(b) substitution to form halogenoalkanes, e.g. by
reaction with HX(g); or with KCl and concentrated
H2SO4 or concentrated H3PO4; or with PCl3 and
heat; or with PCl5; or with SOCl2
(c) the reaction with Na(s)
(d) oxidation with acidified K2Cr2O7 or acidified
KMnO4 to: (i) carbonyl compounds by distillation
(ii) carboxylic acids by refluxing
(e) dehydration to an alkene, by using a heated
catalyst, e.g. Al2O3 or a concentrated acid
(f) formation of esters by reaction with carboxylic
acids and concentrated H2SO4 as catalyst as
exemplified by ethanol
3. (a) classify alcohols as primary, secondary and tertiary alcohols, to include examples with
more than one alcohol group
(b) state characteristic distinguishing reactions, e.g. mild oxidation with acidified K2Cr2O7
, colour change from orange to green
4. deduce the presence of a CH3CH(OH)– group in an alcohol, CH3CH(OH)–R, from its
reaction with alkaline I2(aq) to form a yellow precipitate of tri-iodomethane and an ion,
RCO2
5. explain the acidity of alcohols compared with water
Primary, Secondary, Tertiary
Alcohol
Butan-1-ol
Butan-2-ol
Butan…. (tertiary)
How it produced?
H2O
Reagent??
Reagent??
Catalyst??
Product??
MEchanism
Diols
SN2
Product
LiAlH4
(Lithium tetrahydridoaluminate(III) /
NaBH4 (Sodium
tetrahydridoborate)/ H2
Nickel
Heat
Hydrolysis Ester
Acid → Alcohol + Carboxy Acid
Alkali → Salt + Alcohol
Reaction of alcohol
Combustion
SN
Substitution
O2
Halogenoalkane
Na
Oxidation
(6+) Orange → Green (3+)
Sec → Ketone
Primary → Aldehyde
Dehydration
Alcohol → Alkene + Water
Esterification
+
Carboxylic acid → ester + water
TEsting alcohol
Ethanoyl
Chloride
Tri-iodomethane (also called iodoform) is a yellow precipitate
The reagent is heated with an alkaline solution of iodine
Reaction
Produced
Alkane
Alkene
Halogenoalkane
Cracking longer
alkane,
petroleum FD
Cracking
(Catalyst ….)
Dehydration
Alcohol
Substituon H.A
+ NaOH
(ethanolic)
FRS
E.A Alkene X2,
HX
Alcohol
Sub Alcohol with
HX, PCl3, PCl5,
SOCl2
Reacts
Combustion
FRS
H2
H2O
X2
HX
Ac KMnO4
(hot/cold)
NaOH
(Ethanolic), Aq
KCN
NH3
AgNO3 (ethanol)
Observation
Mechanism /
additional
IPT
E.A
Broken double
bond
SN1
SN2
Water vs
alcohol acidity
level….
Carbonyl
Aldehyde,
Ketone
Produced
Reacts
Mechanism
Carboxylic acid
Ester
Amine
Nitrile
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