CHEMISTRY CHEAT SHEET

PHYSICAL AND CHEMICAL PROPERTIES

ATOMIC STRUCTURE
Property Explanation
The 4s orbital is The 4s orbital is at a lower energy level than the 3d orbital, following
filled before the Aufbau’s principle, orbitals of lower energy are filled up first.
3d orbital
Electrons are first When the 3d orbital is filled, it descends to a lower energy level than
lost from the 4s than the 4s orbital, causing the 4s orbital to be further away from
orbital the nucleus, enabling electrons to be lost from the 4s orbital first
Cr has one Chromium has one electron in its 4s orbital to minimize electron-
electron in its 4s electron repulsion within the 3d orbital
orbital
Cu has one Copper has one electron in its 4s orbital to form a symmetrical
electron in its 4s charge distribution around the centre, forming a full metal centre
orbital
Subsequent IEs Subsequent atoms are being removed from a nuclei with an
are higher increasing positive charge, making them more difficult to remove
IE increases Across a period, there is increasing nuclear charge, but
across a period approximately constant shielding effect from inner shell electrons,
leading to an increase in effective nuclear charge (electrons are
harder to remove)
1st IE of Al < Mg Al: 1s22s22p63s23p1  Al+: 1s22s22p63s2 3p electron is removed
1st IE of Be < B Mg: 1s22s22p63s2  Mg+: 1s22s22p63s1 3s electron is removed
2nd IE of Si < Al Less energy is required to remove a 3p electron compared to a 3s
etc. electron since the 3p electron is higher in energy, it has a lower
penetrating power and is thus more easily removed
1st IE of S < P For S : removal of a paired 3p electron
1st IE of O < N For P : removal of an unpaired 3p electron
2nd IE of Cl < S Repulsion between the two paired 3p electrons in S make it easier
etc. for one of the electrons to be lost, hence the IE of S is lower
2nd IE of Na >> Mg Na+: 1s22s22p6  Na2+: 1 s22s22p5 2p electron is removed
Mg+: 1s22s22p63s1  Mg2+: 1s22s22p6 3s electron is removed
The electron removed form Na+ is in the 2nd principle quantum shell,
which experiences much less shielding effect from inner-shell
electrons, which outweighs the lower nuclear charge on Na as
compared to the electron removed from Mg+ is in the 3rd principle
quantum shell

Read Mr Wong’s Chemical Bonding discussion at

http://sg.geocities.com/tzeyang111777/chemistry/bonddis2.swf

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 CHEMISTRY CHEAT SHEET
PHYSICAL AND CHEMICAL PROPERTIES

ALKANES
Property Explanation
Non-polar Difference in electronegativities of C and H atoms are negligible
(id-id interactions)
bp/mp increases A larger electron cloud is more easily polarized and id-id
with molecular size interactions become greater, and since boiling involves the
breaking of IMF, bp and mp increases with molecular size
bp/mp decreases A branched isomer has a smaller surface area and hence a lower
with branching extent of IMF between its molecules
Insoluble in polar solvents, soluble in non-polar solvents
Density increases with molecular size; less dense than water
Unreactive Non-polar and saturated and do not contain any region of high e-
density

ALKENES
Property Explanation
Similar to alkanes
cis- isomers have The cis- isomer is polar and has pd-pd as well as id-id interactions,
higher bps than while the trans- isomer has only id-id interactions
trans- isomers
cis- isomers have trans- isomers pack better into a crystal lattice and have higher
lower mps than mps than cis- isomers
trans- isomers

HALOGEN DERIVATIVES
Property Explanation
Less reactive than Highly electronegative halogen deactivates the ring
benzene (in ES)
Ar-X less reactive to SN Partial double bond character in the arene C-X bond due to p-
as compared to R-X orbital overlap with the -cloud
The presence of the e- rich ring hinder nucleophilic attack
Higher bp/mp than The alkane is non-polar and has only id-id interactions, where
corresponding alkane R-X has a polar bond and hence pd-pd interactions. Also, the
number of e- is larger, increasing id-id interactions.

HYDROXY COMPOUNDS
Acidity: The stability of the acid anion determines the acidity of a compound
Ethano < Water < Phenol
l
alkoxide ion is destabilized Neither destabilizing or The phenoxide ion is
by the positive inductive stabilizing effects are stabilized by the
effect of the e- donating present delocalization of the
alkyl groups negative charge into the
benzene ring
Effects of substituents
Ethanol Phenol
e- releasing groups on the hydroxyl carbon e- releasing groups decreases the acidity of
decreases acidity as it intensifies the phenol as it reduces the delocalization of
negative charge on the oxygen, the negative charge on the oxygen into the
destabilizing the anion ring, destabilizing the anion; the opposite is
true for e- withdrawing groups

CARBONYL COMPOUNDS
Property Explanation
Higher bp than corr pd-pd interactions as compared the id-id interactions in alkanes

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PHYSICAL AND CHEMICAL PROPERTIES

alkane, lower bp than lack of h-bonding when comparing with alcohols

corr alcohol
Solubility in water Unable to form h-bonding with water. Higher carbonyl
decreases as number compounds have larger hydrophobic groups.
of C increases; soluble
in organic solvents

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PHYSICAL AND CHEMICAL PROPERTIES

CARBOXYLIC ACIDS AND DERIVATIVES

Property Explanation
Higher bp than corr alkanes RCOOH form stronger intermolecular hydrogen bonds
and alcohols than alcohols because the –OH group is more polarized
due to the presence of the e- withdrawing –C=O group
bp increases as molecular Increase in the number of e- strengthens id-id
size increases interactions
Lower RCOOH are soluble in See solubility in carbonyl compounds
water
More acidic than The RCOO- anion is resonance stabilized due to the
alcohols/phenols delocalization of the negative charge over two highly
electronegative O atoms
Effects of substituents See effects of substituents in Alcohols
Ka increases with number of e- withdrawing groups
Ka increases with distance of e- withdrawing groups from –
COOH

Acyl chlorides Esters Amides

Boiling Unable to form h-bonding, and experience Amides have a –NH2 group
point pd-pd interactions and have lower boiling and can form a higher degree
points than their parent carboxylic acids of h-bonding, and usually
have higher boiling points
than their parent carboxylic
acids
Solubility Soluble Insoluble Fairly soluble in water due to
(non-polar RCOCl hydrolyzes h-bolding
solvents) rapidly in water to form
RCOOH
Solubility Solubility decreases with size of Generally insoluble (lower
(polar hydrophobic group amides are soluble)
solvents)

Ease of SN
RCOCl
Highly polarized alpha-
carbon as it is bonded to
two highly electronegative
atoms
sp2 hybridized C
experiences less steric
hindrance (trig-planar)
> RCl > ArCl
Less polarized alpha-carbon Electron-rich benzene ring
as it is only bonded to one repels nucleophile
electronegative atom
sp3 hybridized C Partial-double bond
experiences more steric character makes C-Cl bond
hindrances (tetra) harder to break

NITROGEN DERIVATIVES
Property Explanation
Higher bp than corr O-H h-bond is stronger than N-H h-bond as O is more
alkanes, lower bp than electronegative
corr alcohols
bp increases with Increase in size of electron cloud increases polarizability
molecular size resulting in greater IMF
Lower members are h-bonding with water formed easily for both amines and
highly soluble in water amides; solubility decreases in higher members due to greater
(max 5C in amines) hydrophobic nature (also, phenylamine)
Amides are polar The highly electronegative N is bonded to H, forming h-
bonding
Tertiary amides have They do not form h-bonding with each other due to the
low bp absence of a N-H bond, however the form h-bonding with
water and hydroxylic solvents
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PHYSICAL AND CHEMICAL PROPERTIES

Amides are neutral The lone pair on N id delocalized over the O-C-N moiety

Basicity of amines: The ability to donate the lone pair on N determines basicity
ArNH < RR’R’’N < NH3 < RNH2 < RR’N
2 H H2
The lone pair on N Tertiary amines have Electron releasing R groups increase
is delocalized into relatively low basicity basicity as they increase the electron
the benzene - due to steric density of the lone pair on N, making it so
cloud, making it hindrance from three very big more available to accept a proton
less available for bulky R groups
dative bonding
Effect of substituents on ArNH2: Kb decreases with e- withdrawing substitutents, and vice
versa

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