i

Fitz
i H who
cares
H H
H

Organic Chemistry
Perfectionalis Ultimate
Notebook PUN

OH
H
Cl
CH3 H
Tt Cz
y CHz
Br

The practice questions and answers

are available in another PDF

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Bio logy QUESTIONS

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F Éi
É ii
I
INTRODUCTION.IE
m.io
to
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IjLIchemistry
Scientific
ii
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Figures
ooo s most Notation AiÉ

ij
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Compounds
subatomicparticles
Chemistry
aware.ie

11 Atomicnumber
Its gonna IP.e.ioii.I.e.n.ds
I.IE i I tt i É
Na
sodium
22990amu
symmedement

Atomic
of
name element

mass
jjj.IE
I Iii
Na p Na
i L
j
Its
I s
number
mass i
 Important Equations
Acid base Equations
t
pH a
HzO
POH coli
pH log 430 POH log Lott
POH pH 14
POH
20
PH OH y yo
430 3
14 pka log ka
430 OH 3 1.0 10 M
Strongeracids Ka
Higher
1
Kw 430 3 OH 1.0 10 lower pka

distance movedby spot

Retention factor R
distance movedbysolventfront
aka Retardation factor
 Outline
1 Basics IUPAC
2 Isomerism R vs s configuration
3 Sp Sp sp orbital hybridization
4 Nucleophiles Electrophiles SNL SNL
5 Alcohols phenols
6 Enols Enolates
7 Aldehydes ketones
their derivatives
8 Carboxylic acids
9 IR spectroscopy H NMR
10 purification chromatography
Separation
 Periodic Table
C N O F
Si P S Ee
BE
electronegativity

sit
themostelectronegative
By electronegativity ite mostsatisfiedwithits
e
C N O c p
negativity

Functional Groups
Aldehyde Group KetoneGroup AlcoholGroup carboxylicacidgroup ester Amides
O O O O
P
C C R OH C C C
R R OR R NHz
R H R R OH
Name Ql name one Name Ol name oicacid Name Oate Name amide
Anhydrides Amines Imines
Alkyl halides
O O
Nam R M
C C
R R X
R2 R C Rz
R O R
Name Oic anhydride name amine
 Carbonyl group

g found in
Aldehyde Group ketoneGroup

dipole
g S
08 Aldehyde NO R H R R
Name one

g ketone group Carboxylicacidgroup ester

S o 0
canact as
Carboxylic
acid C C
R OH R OR
ectophile nucleophile É Ester
group an name
si oak
deophilic
I
Amide Amides

Editions
condensation
reactions Q
Anhydride R C NHz
Name amide

Types of carbons

Methyl carbon In carbon 27 carbon 37 carbon

H
O
H G LG 0 O

H 2
LG 4T carbon

O 0
LG
o O O
T
IM leaving group
 Carbocaions
Methyl In 2ns zry
carbocation carbocation carbocation carbocation

H
EH t t
t

H
p
Unstable carbocations the moststable
say
Do Not form in
Snl
i The quickestto
That's why methyl IM carbons form in Snl
do Not participate in Snl
Morestable

Benzylic Allylic 37
Carbocaions carbocaions carbocaions
Resonance Resonance

Ring
 OH

IUPAC Cl

Naming Br

Mr Adam Smith Jr
Prefix First Name Last Name Suffix

Substituents of carbons type ftp.t.giarity

functionalgroupsthat of the chain group
are not part the
of
parentchain

Steps of IUPAC Naming da s

Find the longest carbon chain give it a root name
or add its suffix
Identify the highest priority functional group Adamsmith Jr
to the root name

substituents their positions on the carbon chain

Identify the types of
then add a numbered prefix to theroot name
Mr Adam Smith Jr
 Name the chain based on the number of carbons

1 Meth 11 Under
2 Eth 12 Dodec
3 Prop 13 Tridec
4 But 14 Tetradec
s Pent 15 Pentadec
6 Hex 16 Hexadec
7 Hept 17 Heptadec
8 Oct 18 Octadec
9 Non 19 Nonadec
10 Dec 20 Eicos

A matter of priority O The most oxidized

carbon
Carboxylic acids g

POOH
c
Aldehydes R H
O
ketones C
R R2
Alcohols R OH
Double Bonds C C

Triple Bonds C C
 Functional
Group Prefix Suffix
Carboxylic acid carboxy oic acid
Anhydride Alkanoyloxycarbonyl anhydride
Ester Alkoxycarbonyl oate
Amide Amido or carbamoyl amide
Aldehyde formyl or oxo al
ketone keto or oxo one

Alcohol hydroxy ol
Alkene alkenyl ene

Alkyne alkynyl yne

Alkane alkyl ane
 first substituent substituent first
substituent substituent

ortho para meta

O p m
 Cyclic Amides lactams

B B d
O B
O O s a
N S
H O N O
E
Y H N
H
O

B lactam T lactam s lactam E lactam

cyclic Esters lactones

O O
0
O

0 a 0 a
0 a
o x B r S B
s y

L Acetolactone B propiolactone 2 butyrolactone 8 Valerolactone

 H O H
H
C g
É H g
en OH C H

CHIH CH OH
Isontetism
Mirror

CH3 043 8
cuz H H 11
OH Br OH Br
H H H H
H H

similar piece conditions COOH COOH

samechemicalformula
Isomerism butdifferentstructures Han
g
H H C NH
R
mirror images
Chiral like yourhands sI Notegittpetrintposable

Achiral
ea aforks III ftp.agse INOinternalplaneofsymmetry
Ifi p My
Mirror images reflected
across an axis CH3 OH HO CH
mm
Superimposable
look identical whenplaced on top of one another
SEelideoisomers same atoms linked in thesameway
thenonsuperimposable
but organized differently in space egonemaybethe other
imageof
Enantiomers Not superimposable mirror
chiralcenter
Opticalactivity A G youneedtohave NO internalplaneof symmetry
 oldsystem D CL canonlybeestablished
D L experimentally bypolarimeter
NB Stereochemistry is denoted by CR s canbeestablishedbythe

Newsystem R S priorityofgroups
aroundthechiral
Carbon bypenorpaper

Whereas

Optical Rotation is denoted by

Rotation Rotation
ofplane polarizedlight

R
just because you're D doesn'talways mean you're

isomers samechemical formula butdifferent structures

Co Hiro
Stereoisomers opticalisomers samechemical formula
butdifferent spatialorientation
Carbonyl

H O H O H
carboys g g C CHIH

H C OH H C OH OH C H C O

OH C H OH C H OH C H OH C H

H C OH C H H H C OH
OH C OH

H C OH H C OH H C OH H C OH

CHIH CHIH CHIH CHIH o

D glucose D galactose D mannose D Fructose

 theonlythingtheyshareistheir
sameatoms linkedinthesameway
butorganizeddifferentlyinspace ysameatz.gg y enoncneegg

If
stereoisomers constitutional isomers
Does notrequire structural isomers
IT
qIvert differinrotationaroundsinglecobonds
breakingbonds
to 2 4 q
req interconvert
CONFIRMATIONAL
CONFIGURATIONAL OH 3
isomers

L
isomers thesamemolecule differentpoints initsnaturalrotations y
no
mmmm Ctb 93,0 j
it no
norimages
chiral H H th th n at

Enantiomers opticalisomers Diastereomers cantstaggered staggered

Gaucher
ci iipseds eclipsed

the
are propertiestherefore
chemical physical
same Meso compounds
it'shardtoseparatethem Differinattleastone butnotall ChiralCarbons
mirror
NOT identical
I gempigggr

NOT superimposable
NOT superimposable
Ointernalplaneofsymmetry
Epimers Geometric isomers
4dg
gigs configurational Diastereomers
differinarrangementaround animmovablebond
eggig's.firIikecycloalkane
H OH se y
g Differin exactlyone Chiral Carbon
a gang

schoH OH B OH Br
2 pent2 ene E pent2 ene
Cis pent2 ene Trans pent2 ene
212,45 4 Bromopentan 2 01 125,4514 Bromopentan 2 ol

Tautomers isomers that differ in the placement of the doublebond or a proton

isomers
Ht
a
Entente
Tautomerization movement
of doublebond or a hydrogen

Tautomerization
kenolization
Kg enol

Tautomerization
Imines Examines
C N NHz
N H

Aldehydes or ketones with chiral a carbon will become a racemic mixture why
Tautomerization
enolization
L racemization
keto enol
 CONFORMATIONAL isomers conformers most
similar
differin rotation aroundsingle 6 bonds
in its natural rotation
thesamemolecule different points

CHz HH
Lfo H
CHz

Thesmaller the angle between

the 2 CHz the greater
the strain higherenergy less favored
CH3 00
688h
CH3 CHz CHz 40h3
µ µ H CH 1200

H
H H H H HH H H CH3
CHz H H H
antistaggered Gauche staggered Itdipsed Eclipsed

iftheenergydifference leastfavored
jzCHz Absolutezero ok norotation
issmall easyto ingtergeticity

overcome roomtemp
iRotationhappens roomtemp
HH H
H
CHz s
H ÉÉipsed a 1200
1200

H CHz
CHz H
got H H H
H Eclipsed

Maim

É antiperiplanar cHzG eCH3 04369

H p 1
043 CHzGab
µ H m
H H H H
H H
H H Mostfavored
H H
q energetically
staggered
staggered
leaststrain staggered cuz
catsgroupsareantiperiplanar staggered

Rotation
 Cyclic conformations Ringstrain
of cycloalkanes
strain ATTÉITT Nonbonded
strain
stericstrain
VanderWaals
Whenbondangles repulsion
deviatefrom Eclipse or or
atoms groups
nonadjacent

idealvalues gauche for

the
compete same
space

flagpoleinteractions
I Nonstiated

strain
steric The
most
stable
Chair
botatoat
Twist cyclohexane
Boat cyclohexane lessstrain morefavored
cyclohexane
chair boat
Equatorial axial because
e quatorial slot.fi
eIaYtions

mnemonic
Nothingismorestablethansittingon a Chair
theEquator
Floatingin aboat is unstable

Afterachairflip groupsbecome equatoria

Chair like configuration A'Atiguatorial axial
groupsbecome
alldashesremaindashes
remain wedges
C Agggs
O 6 O Mutarotation 0
I
egg
H H p e

10
chairflip
CHOH
OH
OH OH H 18 e to
OH 0
on digger
H OH
L D glucose B D
D glucose gycose
equatorial
unlike dxial justlike Chou
guy down
Cis to CHOH
trdns to CHOH
CHIHisupbut OHisdown D ftp.inc p lessfavored
CHOH
Both OHare
up D Strait gagged

underalot of y B isBeautiful

steric hindrance steric hindrance

i It will assume a chair like configuration
Isteric strain steric strain
Whathappens if weexposeHemiacetal rings to 420
forthbetweentheopen orclosed
theywillcycle backer form É
couldbe
L or
B Lutarotation Mixture
af LY
around Cy qq.gg
spontaneous change
of configuration
lessfavored
TJ
Glucose
31 morefavored

mnemonic
Mutatis Mutandis Nothingismorestablethan sittingon a Chair
theEquator
 CONFIGURATIONAL isomers
mirror images
Chiral likeyour hands sI Notegittpetrintposable
LNOinternalplaneofsymmetry 11,1 MY
mirrorimages
M
AeaChiral s
a forks
Superimposable

Chiral center
center
a carbon that is an asymmetrical core of opticalactivity
stereo
theasymmetriccenter has No internalplane of symmetry
F Chiral carbon
F
H CH3
H singlebonds sp hybridized Tetrahedral
CH3 I

tenaneignposa

What is racemic epinephrine

a mixture of D CL epinephrine
50 50
cancel each other out
they
i NO optical activity to the mixture
 Enantiomers
isomers samechemicalformula but different structures
I d
2
orientation
Stereoisomers opticalisomers samechemical formula butdifferent spatial
mirror NOT identical NOT superimposed
OppositeAbsolute congas

Carbonyl aldehydegroup Carbonyl aldehydegroup

carbon O H cargo O H E
Éas
C U I C Es o
a
chiral H C OH gird OH C H 3
carbon

tyI 3
CH OH CH OH
s

D Glyceraldehyde ment L Glyceraldehyde a

oppggation g
É numberofchiralcarbons
the number of stereoisomers with a common backbone 2

mirror
chiral Enantiomers NOT identical
not superimposable
NONsuperimposable mirror images Nointernalplaneofsymmetry
them
Theyhavethesamechemical physicalproperties thereforeit's hard to separate
exceptby I
How can we tell them apart I opticalactivity
Plane polarized light 2 Reactions in chiralenvironment
Levorotatory Dextrorotatory

A singleEnantiomer of a chiral molecule can rotate light left or right

clockwise
this optical activity is measured via a polarimetereunterdockwise

indegrees D CL canonlybeestablished
A observed experimentally bypolarimeter
A
specificrotation
angle
C theofthe
R S canbeestablishedbythe
priority ofgroups
around thechiral
theConc in thelength
g pathtubesthrough
which
Carbon bypen orpaper
ml lightpasses
in dm

D CL ofcarbs a a refer to
theabsolute configurationof glyceraldehyde
 Theyhave I chiralcenter Diastereomers II.aefjor
NOT superimposable

Differ in at least one but not all Chiral Carbons

can
theythave different physicalproperties to separate via
easy
Filtration
Crystallization
they have different chemical properties Distillation
but they behave similarly in somereactions
may
because have the same functional groups
they

Stereoisomers

DifferinattletastoneChiral Carbons

mirror WI identical
mirror
NOT identical Not superimposable
NOT identical
NOT superimposable Diastereomers Not superimposable
Enantiomers Enantiomers
carbonyl
carbon
H O H y
my g g
o
c g
HO C H H C OH H HO C H
C OH
HO C H H C OH H C OH
HO C H

CHIH CHIH CH OH CHIH

L Erythrose D Erythrose
L Threose D Threose
Epimers

DifferinexactlyoneChiralcarbon
 Enantiomers Diastereomers
mirror images Not mirror images
NOT identical NOT identical
NOT superimposable NOT superimposable
They have the same physicalproperties they have Different physicalproperties
easytoseparate via
Filtration Distillation
exceptoptical activity crystallization

they have the same chemicalproperties mayhave Different chemicalproperties

buttheymaybehavesimilarlyinsomereactions
exceptreactionsin chiral environments
theyhavethesame
because functionalgroups

if one is D theotherhastobel if you know the opticalactivity one of

and vice versa youcan't predicttheother one
t O H O H O H
19 c c g
to C H H C OH H C OH H C OH
to C H H C OH H C OH HO C H

CHIH CHIH CHIH CHIH

L Erythrose D Erythrose D Erythrose
L Threose

Geometric isomers
immovablebond
o singlebondfreelymobile

differ in arrangement around an

e.g double bond or
ring structure cycloalkane

pent 2
2 ene E pent 2 ene
Cis pent 2 ene Trans pent 2 ene

For simple compounds only I substituent Cis Trans

Forcomplicated compounds 1 I substituent Z E IUPAC
Mensaggiramicenteds
Mesocompounds
2halvesofthesamecompoundthataremirrorimages
has internalplaneof symmetry
2halvesofthesamecompoundthataremirrorimages
Notopticallyactive
chiralcenter
Opticalactivity A G youneedtohave NO internalplaneof symmetry
Racemicmixture contradictionbetween
Internalplane
of symmetry couldexist 2 molecules
Through the chiral center Mesocompound contradictionwithin the
Between chiral centers samemolecule
If a compound has internalplaneof symmetry i Itwill Not have Opticalactivity
chiralcenter
COOH Meso compounds
OH internalplane
µ of symmetry
chiralcenter cook
meso tartaricacid
IR 25 I 2 Dimethylcyclohexane

Enantiomers Meso compounds

mirror images mirror images
NOT identical identical
NOT superimposable superimposable
have chiral centers have chiral centers

NO internal planeof symmetry have internal planeof symmetry

The molecule as a whole is chiral The molecule as a whole is Achiral

i has optical activity has No optical activity
chiralcenter chiralcenter
COOH
chiralcenter
COOH t
0004 0001
O Ho H
a
µ OH H writer
HO
chiral
center
cook
chiralcenter
COOH
airalanter goof 0001
L tartaricacid D tartaricacid meso tartaricacid meso tartaricacid
 theonlythingtheyshareistheir
sameatoms linkedinthesameway
butorganizeddifferentlyinspace ysameatomic samestructuralbackbone
p mg.gg
stereoisomers constitutional isomers
Does notrequire sn ji

i
reqYÉ 1Éert breakingbonds
to
interconvert
differinrotationaroundsinglecobonds

CONFIRMATIONAL
2 4
2
I 3
CONFIGURATIONAL OH
a isomers
thesamemolecule differentpoints initsnaturalrotations

norimages µ
Ctb
a cis jig 430 act's

chiral H H th th n as
oh H Gaucher
opticalisomers Diaster Mers cant H
staggered
s taggered ciciipsed eclipsed

the
are propertiestherefore
chemical physical
same Meso compounds
Differinattleastine butnotall ChiralCarbons
ygfjyifgg mgyqyd.to
them
separate

NOT identical NOT superimposable

NOT superimposable
Ointernalplaneofsymmetry im

1 Epimers Geometric isomers

gig joy configurational Diastereomers
differinarrangementaround animmovablebond
egg
gb's.fi r iikecycloalkane
H C OH girl OH C H Differin exactlyone Chiral Carbon
Chou Chon B OH Br
2 pent2 ene E pent2 ene
cis pent2 ene Trans pent2 ene
a.m

Is the molecule as a whole Chiral

Does a chiral center exist

F No

Does I chiralcenter exist Achiral

Yes NO

Is there a superimposableimage Chiral if moleculeis Chiral

or opticallyactive
internalplaneof symmetry k Achiral NOToptically ay
µ NO

Achiral q
 the TischerProjection
Horizontal lines wedges out of thepage
Br
Vertical lines dashes into the page
A
nanny g g g ne y CH z

CI

Titian H Br

We want the lowest priority group to project into the page

 R S Configuration
F F

H H CH

CHz I I
Chiral mirror

Absolute Configuration
The chiral carbon R S
the atoms around it
number
the order of theseatoms by the atomic
steps lowest
Rank atoms groups from highest to priority bytheatomic number
your
i.e ignore it
Make sure the lowest priority is the back

Look at the remaining 3 atoms groups

Only 4 possibilities of problems
draw an arc the back
4 is
A If clockwise R 4 is the front
9 If counterclockwise S longchains zoom in
4 is neither the back nor
thefront
 AtomicRadius decreases

H He Eo
Li Bei B E N O F Ne a

gÉfÉÉi in Al si p S CI AF
i MEgo over an ape Ga Ge As set Ber ki o
a
Ag Cd 8
pp Sp I

Highfority
logriostity

H e c e n c o c F e p e s e Ce Bre
I

Q What if the lowest priority group is neither front nor back

other
A swap 2 atoms with each

I single swap i.e

you
swapped 2 atoms once Enantiomers

É 2 swaps ie
you
swapped 2 atoms twice the same molecule
ÉT3 swaps ie
you
swapped 2 atoms thrice Enantiomers
atoms 4 times
4 swaps ie
you swapped 2 the same molecule
Think of I swap as equivalent to a rotation of 180
Odd of swaps Enantiomers
Even of swaps the same
 Hybridization I

sp3 sp sp
c c c

170 ofatoms e groups

aroundthe shape
central atom angle domain geometry
1800 170 ofe
360
2 180 2 linear
1200 360
3 1200
3 Trigonal planar
not 3D
1095 360

4 109.5 4 Tetrahedral
3D 3D

90 120 Trigonal
5 3D 3D Bipyramidal
6 90 Octahedral
3D
 gaÉ angle domaingeometry This tablerepresents the
c
180 360 ideal angles
2 1800 2 linear i.e When all the e groups
1200 360 Trig.gg planar
1200
3 aroundthe central atom
3
109.50 360 are bonding pairs
4 109.50 4 Tetrahedral
3D
But what if lonepairs
5 it
90 120 Trigonal
Bpyramidal are present aroundthe
central atom
6 90 Octahedral Then ANGLE DISTORTION
takes place
Reduction in theideal angle
Examples H why
Nhs n inthe
lone'pairning belonepairs pushdown on the
deal 10704ft bondingpair ANGLE DISTORTION
covalentbonds H son H
loneFair
Trigonalpyramidal

egging lone
pairs
O inthe
egg
ideal 104.50
tqheteigfagagg.ie

H 204.50 H

the greater the no of lonepairs the greater thereduction in theideal angle

The smaller the angle

But what if lonepairs arepresent aroundthe centralatom

Then ANGLE DISTORTION takes place Reductionin theideal angle why
ble lonepairs pushdown on thebondingpair ANGLE Distortion

Examples H
lonepair Reduction
NH3 µ
in the the idealangle
ideal 10704ft
weexpected H H107 angle
atetrahedral a lonepair Trigonal pyramidal
scovalenggy
Reduction insteadof
lonelpairs in the
104.50 theidealangle
Totalis 4 2 covalentabonds ideal of 109.50
we
a
tetrahedral
expected
2 lonepairs
H 204.50 H
de
Bent molecule shape
thegreaterthe no of lonepairs thegreatertheReduction intheidealangle
Thesmallerthe angle
 e domain geometry molecule shape
b
where
onlyrefers toplaces onlyshowthe effect of
sharedpairs
electrons r the lonepairs of e s
there are or
Ilonepairs and not the e s themselves
eg the molecule 4 e domains
of these 4
between
only 2 are
sharedpairs
of e

0 H
i e domain geometry is tetrahedral molecule shape of tho is bent

The bent structure

e
What
domain geometry
piananif e
Tetrahedral
domain geometry

Thebondangleforthe Thebondangleforthe
final molecule final molecule

1200 109.50
 nucleus

2
4
2 2
I 2 2 p2
carbon

Px Py 212

Theleastamountof
energy is neededtobreak it

Bonding Pair easiest

Covalent to
shared break
Bond
weakest
I e
pair single longest
2 e pairs Double
3 e
pairs Triple shortest strongest
Hardest
to break
Needsthemost
energy
Geak

Single is Sigma A bond

I 6 bond
Double
I TI bond
Tl
I 6 bond
Triple 2 IT bonds
Tl
 Sigma A bond Pi T1 bond
Single bond Tl bond
can exist to Double É Metistwith
I Double independently a 6 bond

Triple
type
a
ebon
2 IT bonds

I
Head to head or Tail to tail overlap 2 P orbitals lineup Parallel side by side
collateraloverlaps above below
O
pp
O bond is Strongerthan TI bond IT bond is weaker than bond
bond pure or hybrid overlap
Canresultfrom
the overlapmust be unhybridized fo a
overlap pure
s
sp Pure
s overlap hybrid
P p overlap pure
Affects theshape of the molecule No effect on theshape of the molecule
 bond
If the Signs are the Same
theresulting bondingorbital canresultfrom
overlapereafetail to tail
is more Stable This
a 6 bond s s overlap

i 3
Bonding p p overlap
Molecular
sorbital sorbital Theyhug orbitals

Molecular
Sorbital Sorbital Theydon'thug orbitals

Bonding
d Molecular
Sorbital P orbital orbitals

A XD Bonding
Molecular
P orbital P orbital orbitals

Pi T1 bond

2 p orbitals lineup Parallel side by side to one another

collateral overlap above below the plane of the molecule

FIJI
pp
 trength is additive

stronger stronger
than than
0
IT Triple to Double Single
Requiresmore
energytobreak

shod th
bond is I bond
Requiresmore
energytobreak

In a to Double bond it's easier to break the T than the 6

Cis
requires
bondbreaking traps we onlybreak the Tl of the to Doublebond

Sp3
H
Unhybridizedorbitals

2 2 2
H C H É
z
Px Py Pz

H Hybridizedorbitals

25 2P 2 2
4 groups Tetrahedral Py Pz
5 PPP
109.50
Sp3
 Sp Sajid
Unhybridized orbitals
T
C c Px Py 212
H 2

Hybridizedorbitals
It
saved for
congreatingbondsty c c a bond
6bondsareformedfnmhybtidobitals.my
EEtibondsmarefemindorbitalsy 25 2P 2
Py
2
Pz
5 PP
3 groups Trigonal planar
2200 gp2

saved for
Sp 2T bonds
Unhybridized orbitals

T
H C F C 2B Py 2Pz

Hybridizedorbitals I saved for

nonreatingbondsly C C 2T bonds

Obondsareformedforhybridobitatsry
Rich bonds are formedfrom orbitals 25
2B 2Py
2
Pz
Lunn 5 p
2 groups linear
1800 Sp
 numberof numberof Geometrical
Angle
S P
groups t bonds shape character character

sp 4 Zero Tetrahedral 109.5 251 75

Sp to 3 I Trigonal planar
nots 1200 33 67

Sp o
2 2 linear 180 50 50
Tl

doublebond
Resonance or
ring
Resonance Restricts free rotation
partial double
bondcharacter more Rigid structures more stable
Example Ozone Oz
É Resonance É É
1 O o o

Example
R
É Nha
Proteins Their amide linkages between their a a

have Resonance Restricts free rotation

more Rigid structures
 to
Organic Reactions
Ht mid Base
OH

If
otto
selections
HI
Badi

E Ni
É
Electrophile Nucleophile

Acidic
Ka Ka
Basic

t t t t t t i i n i n t P

Acid base Equations

t
pH a
430 3
POH of
pH log Hot POH log OH

POH pH 14
POH
20
PH OH y yo
430 3
14 pka log ka
430 OH 7 1.0 10 M
Strongeracids Higher k
14
Kw 1430 31 OH y 1 Ox 10 lower pka
 WHAT'S AN ACID

A substance that yields H when dissolved in water Arrhenius

molarity
X t H2O D t Ht
1H
releases
Monoprotic
Hydronium
the Diprotic releases
21ft
type
Triprotic releases
3Ht HtquicklyH2o Hzot
A proton H donor
Bronsted Lowry
NHj J
Bronstede.tw
H D H NHz

An electronpair 2é acceptor Lewis acid

Gilbert Lewis

H NH D H NH
t t
Lewisacid Lewisbase

it
because acceptselectrons donateselectrons

WHAT'S A BASE
A substance that yields OH when dissolved in water Arrhenius
X t H2O D t OH
srawback cannot explain bases like ammonia NH3 or sodium carbonate Naco
A proton Ht acceptor Bronsted Lowry
BronstedLowry
Bronsted
If H NH Jase D H NH

An electronpair 2é donor Gilbert Lewis

H NH D H NH
 Water H2O

acidic solution basic solution

Amittoteric acts acid

acts as a base as an

H2O accepts Ht from an acid H2O donates Ht to a base

kinetics
yields
at bB act dD
Teactants product
for a reversiblereaction
products
Konstant
reactants stoichiometric
d coefficients
C D
coding
concentration

A B
High K value the conc of products 7 the conc of reactants Equilibrium

Low k value the conc of products the conc of reactants Equilibrium

 The strength of acids or bases

Strong acids fully dissociate

morettroducts
HA Ht A

Konstant
products
K HYLA stronger acids
reactant HAI Higher K

Weak acids partially dissociate

lessÉÉÉucts
HA Ht A
weakeracids
Products
K
Ht AT lower K
Konstant
reactants
HAI

Stronger acids Ht
Higher lower pH
Weaker acids lower Ht Higher pH

pH log Ht

pka log ka
Stronger acids Higher K lower pka
Weaker acids lower k Higher pka
Bases even lower k even Higher
pka
 cc
I love Sarah

IÉ
1 e

Nucleus is
i
Electrons are

If I am a
attracted to attracted to

gym lie attracted tonucleus

I am an electrophile web I am a nucleophile

isegative
Electrophile is Nucleophile
E Nii

Nucleophilic attack

The Nucleophile attacks the Electrophile

the Negative attacks the

selections
BEKELE
covalent

Nu
bone
E
Electrophile
Nii
Nucleophile
E T
electronpair electronpair c rdinate covalent bond
Bothelectronscamefromthesameatom
2e 2g
acceptor donor
 Nucleophiles Electrophiles
selections
Backside
attack

E Ny
Electrophile Nucleophile

Snl Snf reactions

A Lewis acid is an electronpair 2é acceptor

H NH D H NH
Nucleophile T t
Lewisacid Lewisbase
Electrophile acceptselectrons donateselectrons

selections
BEKELE

H NH H NH
acceptselectrons donateselectrons
T
C rdinate covalent bond
Electrophile Nucleophile Bothelectronscamefromthesameatom
Lewis Acid Lewis Base
Mnemonic
EA sports mnemonic
N.B

A B A B
T t g
Lewisacid Lewisbase C rdinate covalent bond
Bothelectronscamefromthesameatom
acceptselectrons donateselectrons
 I

acceptselectrons donateselectrons
Electrophile Nucleophile
Lewis Acid Lewis Base
Mnemonic
EA sports mnemonic
NB

N Rs
R
I NH Nitrogen
Nitrogen based
functional groups
Amine's
Amides
BIDEN
Nitrogen loans a
lone pair of electrons
Nitrogen is an electron donor
Nitrogen is a Lewis base
i Nitrogen is a Nucleophile Et N
MHz is a Nucleophile Tautomerization
Imines Enamines
Hydrogen Cyanide HCN is a Nucleophile C N at Nigg tain
N Rz
HCN H C N
R C R

I
 Nucleophile Electrophile
Contain a pairof electrons or Acceptsthe pairof electrons fromthe Nucleoph
a Tl bond Needs an emptyorbital or
a leavinggroup LG

harge Negative or s Positive or st Electro

donates electrons accepts electrons

Lewis Lewis Basethemorebasiothenudeophile

themorereactive it is Lewis Acid
unemonic N.B Bid N EA sports
BaseLewisdonates electrons Yggggephile

Alcohol R O
eg R N Rs H H
B state
A
Aldehyder
Amide's positive
C C r.ci
Amines
H H T B
HH ketone
cark iced
CTC H N'C y
CIC
negative
c N strata

É a
on tagging CH djnIatives

Pico CH qty Amydrides

ppA

Kinetics Nucleophile Electrophile

Reaction rate

is is

Thermodynamics
equilibrium position
Base Acid
of the reaction
 Weakbases aregood LGs
takeplaceif thereactants Nii Leaving Group LG G theconjugatebasesofstrongacidsmake
s morereactivethantheproducts LG good LGs e.g I Br Ct

If LG exists the reaction is more likely to take place

If there's an emptyorbital s the leavinggroupmay not be displaced
i e A covalentbond will bemade betweenthe electrophile er thenucleophile
without displacing the LG
electrons after heterolysis
LG is the molecular fragment that retains the

A B A B Alkanes H attest as LG

F LIisbase
g f
Lewisacid c a te t d heterolysis
electrons
accepts donateselectrons formation bondbreakdown Both electrons are
Bothelectronscamefromthesameatom given to 1 ofthe 2 products

In SNreactions theleaving
Nucleophile wants to give away its electrons
group weakerbase is replaced
LeavingGroup Will retain electrons
bythenucleophile strongerbase

ie
Cl

Leaving
Group LG

Formal charge change

from to

or
0 1
I
0
 Snl Sn2 reactions
Nii
LG
C O

Most Organic Chemistry Reactions

Oxidation Reduction Reactions

Nucleophile Electrophile Reactions

Nucleophiledonates e Substitution reactions SN
Sn
Nucleophile accepts H Elimination reactions Et
Ez
 Substitution reactions

LG Na
Nii LG

Elimination reactions

LG
a
Base LG
a

To determine the type of the reaction look at

I Alkyl chain
2 Leaving group
3 Attacking base Nucleophile
4 Solvent

substituted for theleavinggroup

Snl Carbocation Nucleophile

F SN No carbocation Nucleophile
substituted for theleavinggroup

E carbocation I bond between d of carbon

1
I bond between d carbon
Ez No carbocation of
 Substitution reactions
Snl
Nii
LG N
C slow fast LG
ratelimiting

ReactionRate K alky hainI If conc of alkylchaindoubles

1storder kinetics 2 theReaction Rate doubles

Note TheReaction Rate depends only onthe conc ofthesubstrate

The conc of the NucleophileDoes NOT affect the Reaction Rate

Snl
catalyst
CHz
Met Ht ee at H

43EUR
solvent
deprotonate

Netcharge O solvolysis ge
app

OCH3

CHzÉHzCl
Netcharge 0

1 carbocation
Clues 2 steps
2 Solvent replaced the LG
 Sn2

X
L
N
LG

If conc of alkylchaindoubles
theReaction Rate doubles

K aikjiciain If conc of Nucleophiledoubles

ReactionRate
I Nu I theReaction Rate doubles
2nd order kinetics
If conc of alkylchaindoubles 2x
Vote TheReaction Rate depends on Nucleophiledoubles
the conc of 2x
BOTH the conc ofthesumbstrate
theReaction Rate will quadruple 4x
the conc ofthe Nucleophile

Sn2

Br s
NatS H Br
Dmso
polaraprotic

No carbocation
clues gu
I step Nii replaced
the LG
weprefer a minimallysubstituted is achiral
LG e.g methyl or 1 or 2M
but if theproduct is chiral
slow down
Big bulkymolecules SN2 reactions it will have inverted
stereochemistry
 to
Oxygen ornitrogendirectlyattached hydrogen

protonantotent Ct ÉÉr
formhydrogen
g DMF
Nucleophilicity increases as
N
you go Up
ammonia
NH GO
t.no ii amineRNH2 Dmso 5 0 Nucleophilicity Basicity
cat COOH Acetone E GO
water H2O

ÉÉ Periodic Table
Ce
F alcohol
ROH
S
Acetonitrile
CEN
Periodic Table F
Cl
Protic BE
j CH
Iggy
H H B
3
a
g Aprotic
auseit'ssobig
cannotbe
elated thefully
H
O
HS If
by
I Br Ce F F Ce Br 7 I
smalland
obliterated
Strongest
Strongest atomisbiger
Nucleophile bythesurrounding Nucleophile the so
Iis thenegativityisspreadon
i weaknucleophile

I istheconjugatebase F istheconjugate there are no protons to get in theway

baseof HF
of HI
a weakacid
of the attacking nucleophile
a strongacid

How about non polar solvents

We will not use them
We need polar solvents because like dissolves like

DMF Dimethylformamide

HE H
y
Alkylchain DMSO Dimethylsulfoxide
Leaving group
Attacking base Nucleophile
solvent CHz
up
 Unimolecular Nucleophilic Substitution Bimolecular Nucleophilic Substitution
S 1 s 2 Good leaving
group
Depends on L moleculefallingapart Dependson 2 moleculescoming together
thesubstrate losing itsleavinggroup thesubstrate the nucleophile
2 steps I step concertedprocess toofast toostrong
intermediate
1 formation of a carbocation 1 Nucleophiledoes a backsideattack pushesuplettinggrow
2 Nucleophilic attack andstereochemistry getsinverted likeanÉmigré a
Polar Aproticsolvents
Polar Protic solvents Htt Say Nonpolarsolvents
Needs a carbocation intermediate Does NOT need a carbocationintermediate
d
the conc oftheNucleophileDoes NOTmatter thesubstrate the Nucleophile Bimolecular
Therate isfasterwith 3rd substratescompared Therate isfasterwith 1B carbon substrates
to 2rycarbons compared to less substituted carbons
3rd carbons are always Snl 1B carbons are always S 2
29carbonscouldbe Sat or S 2 buttheyprefer S 2
thesame
Stereochemistry stereochemistry is always inverted concertedprocess

Theproduct Amixtureof R S chiralcenter Stereochemistry is inverted blesterichindranceplaysarot

3rd carbons CANNOT participate in S 2

weprefer a minimally substituted
becausethe3rd carbon is attached to
LG e.g methyl or 1 or 2M
many bulky groups steric hindrance
Big bulkymolecules slowdown
By adding a 3rd substrate
youpush SN2reactions
thereaction
away from S and
2 more

towards SNL
 Some rules
SNL slow 5,2 too fast
3rd carbon substrates 1B carbon substrates
2 T carbons could be Snl or 5,2 but theyprefer 5,2

Weak Nucleophile Strong ideophile

2 is 2 strong anucleophile

Polar Protic solvents Ht Snl polar Aprotic solvents DMFacetoRemso

NH3 R NH COOH Hao ROH Non polar solvents Toluene Hexane
When
yousee an ACID as a reactant or Neutral or Basic conditions 5,2
a product
say ay sauce stronger
5
The more negative molecule is
yourattacking
themore
likely it is to attack
the stronger or fasterthereactionis
i Sn2
 LG
H

iii
A
g Br 0 9
H2O H
deprotonate

solvolysis
g
H H
H
H O
0 Br
H H Netcharge O

Sn2
good Leaving group
G strong
nucleophile
t g
C N CN
Br
E Natan H Br
3
a carbon
DMSO 3 a

polarAprotic S
Oxidation Reduction
reactions
Oxidation
Fest Fest
Reduction

OXIDATION IS REDUCTION is
or gainingbonds
Gaining Oxygen tooxygen Losing Oxygen
FFnumberofbonds tooxygen oranotherftp.gaatofory
oldbondbroken bond oldbondbroken newbondformed
c neg fried c z c
y morteelectronegative
y
lesselectronegative negative
mgyaenteleyc.to less electronegative
than than Z
y
Éising Hydrogen Gaining Hydrogen
If numberofbonds toHydrogen IF numberofbonds to Hydrogen

Losing Electrons e Gaining Electrons e

If you'recapable of being OXIDIZED you'reconsidered a REDUCING agent

sugar

i e Whileyou're being OXIDIZED you'reREDUCING someone else

closing e o
 Dehydrogenase Oxidation Reduction Redox reactions
Transfers a hydride ion H to an electron acceptor
such as NAD or FAD to make NADH FADHz

H
NAD X dehydrogenase
C Reducing Redox
NADH X
agiliting agent reduced oxidized
willacceptelectrons will loseelectrons
andbecomereduced andbecomeoxidized

H
FAD X dehydrogenase FAD Hz t
C Reducing
Redox reduced
X
agelizing agent oxidized
willacceptelectrons Wi
ah'dbicomedetidied
andbecomereduced

e.g PDH a KG DH

Oxidizing agent REDUCING agent

If you're capable of being reduced If you're capable of being OXIDIZED

While being reduced whileyou're being OXIDIZED

you're
gained e o c losing e o

You're Oxidizing someone else you'reREDUCING someone else

High affinity for e cking low affinity for e
eg
Oz Oz Cla
CrQA920e.g.Cattz.NaBHysNaH.LiAlH
Na
Cr6tC
2n Al
cr0pT.Mn Mno Mg
NazCrz07 or or Hydroperoxide
ftp.qqryg7
sodiumdichromate
H2O

often contain metals bonded to Often contain metals bonded to

a large number
of O atoms a large number of H atoms
 Oxidation Oxidation
is alcohol Aldehyde Carboxylic acid
Reduction Reduction
OH 2 2
0 0
R OH
CTI RC it
o
2Balcohol Oxidation
ketone c
Reduction R R

OH

Amines Amides
reduction
R NIER P
R C NHz
 Alcohol

ROH

OH
OH
OH
pry 2ry gry

becomes becomes

Acid Base Conjugate conjugate

base of acid of
the acid the base

Reactants Products

The reaction proceeds forwards as long as the

reactants are stronger i.e more reactive than the products

the more stablethe conjugate base the morelikely the proton is tobe lost or
the stronger the acid
 Benzenol Phenol O
OH
hydroxyl hydrogen is acidic why
Oyfthis Due to resonance within thephenolring
Cie the charge on the oxygen is stabilized resonancewithinthephenolring
by
on themorestablethe conjugate base themorelikelytheproton is tobelost or
the stronger the acid
Salt water
att
Base HOH OH
CesNaoh
acid Water deprotonate Hydroxide
Electron withdrawing
Electrongyopsating
groups

e.g No Nth
halides OCH Algy att Alkoxide
deprotonate Alkoxy
Stabilization
ofthe
charge
Destabilization
of the
thruresonance delocalization charge
dacidic 0
Acidity
AcidisanelectronAcceptor
Acidity
Phenols
at't Phenoxide
deprotonate ephenoxy

proton Hydroxide

H2O pka 14.1

Ht OH
No resonance

CH3OH a
Ht Agggg pka 15.5

Phenoxide

OH Ht O pka 10.1

the most acidic why

OH lose a proton Ht
can
resonance within the phenol ring
 Alkylgroups Acidityisaffectedby
innonaromaticalcohols
dib Alkylgroups Acidity Resonancestabilization
Atomidentity
Electron withdrawing Inductiveeffect
OH OH Resonance
groups s characterofhybridorbital
more acidic lessacidic
stabilizationof the charge Acidity
R a sty R H
Destabilization
of the charge Acidity
H fess
a c
aioli gotta
H'acidic
c
Mnemonic Destabilization
ofthe charge Decreases
Acidity

ketones Electron withdrawing

Electrongyopsnating
cop groups

Alkylgroups donation
innonaromaticalcohols
of e density Acidity Acidity Acidity
destabilizethe charge AcidisanelectronAcceptor

Alkylgioups stabilizethe charge stabilityofthe carbocations

themoresubstituted carbocations are morestable
Alkyigioups Destabilizethe charge stabilityofthe carbanion

Alkyigioups
Ketones a hydrogen arelessacidicthanthoseofAldehydes
steric hindrance
protectketonesfromnucleophilicattack theircarbanion islessstable
ketonesare lessreactiveto nucleophilicattack bleketoneshaveanadditionalalkylgroup
compared toAldehydes

Aldehyde Group KetoneGroup

O O
c c
R H R R
Name Ql name one
 Hydrogen bonds one Hydrogen
H O H N H F
11
Alcohol has OH
Hydrogen bonds are possible
5110s Alcohol has higherboiling point
boiling point highermelting point than the
corresponding alkanes
Hydrogen
bonds melting point
Solubility in H2O Thegreaterthenumber
of OH groups
thegreaterthenumber Hydrogen bonds and
of
the higherthe boilingpoint
Boilingpointdepends on
Molecular weight
Hydrogen bonds are non covalentbonds
Hydrogen bonds

Oxidation Oxidation
is alcohol Aldehyde Carboxylic acid
Reduction Reduction
OH 2 2
0 0
R OH
CTI RC it

O
2Balcohol Oxidation
ketone c
Reduction R R

OH

3rd alcohol cannot beoxidized

further

OH
 oxidized oxidized
I alcohol Aldehyde Carboxylic acid
to to 0
O
R OH C
C R OH
R H
Potassiumpermanganate

KMn04 chromium trioxide Silver I oxide

is alcohol strong oxidizing agent eg Cros 1920 Carboxylic

sodiumdichromate potgfju.gg
or Hydrogenperoxide acid
chron

otheragents
1 alcohol eg Pyridiniumchlorochromate Aldehyde
PCC
LackstheH2Onecessarytohydrate
theAldehyde
O
2nsalcohol oxidizedto ketone c
CrozorPCC R R

oxidized hydration Geminal oxidized

1 alcohol Aldehyde Carboxylic acid
to dd to
0
R OH OH
PCC
LackstheH2Onecessarytohydrate
p
g C p
C
on
theAldehyde y R OH

CHOH COzH
Is alcohol 4039425040 Carboxylic acid
Acetone I

2ndalcohol 403942504 8
Acetone g ketone
 Reduction
Reducingagent
OH
LiAlH
Aldehyde 1 alcohol
C or
NaBH
R H

ketone
init 2 alcohol on
C
R R or
NaBHy

Amides
1 Itai ether
R CH
RC Na Amines
Na
2 H2O

Poor Leaving groups

R OH

Protonation

Better Leaving groups

mesylates tosylatesester
803GHz 8036440143
 Better Leaving groups

mesylates tosylates ester

functional
group 503GHz 803844GHz
derived
from methanesulfonic acid p toluenesulfonic acid
How to
Alcohol Base
methylsulfonyl toluenesulfonyl
prepare chloride p chloride
Alcohol ester

structure 950 ester

43C O 0 op
Functions Better leaving groups
Protecting
groups
Protect cover the alcohol prevent it from reacting esp w oxidizingagents

Alcohol
To be protected mesylates tosylates
by Protecting groups eg

To protect others
byacting as Protecting groups

2 RO OR
L'carbon
reactor reducingagents Aldehyde
88 Acetal I'carbon C
LiAltle do Notreactw reducingagents
R
LiAllt

I 2 Alcohols
RO OR
2 carbon
ketone diol Ketal
reactw reducingagents
2ndcarbon
C
LiAltly do notreactw reducingagents R R
LiAllt
 Alcohol as protecting group

HO OR
RIH 1 Alcohol R
C
H
RO OR
and C
OH Hemiacetal ROH R
Aldehyde
L'carbon
in basic
conditions
FemPaedettal H2O Acetal I'carbon
reactw reducing
getts do Notreactw reducingagents
inAcidic Lially
conditions useda'spittecting
groupsforcarbonyl

HO OR RO OR
C
peforge and R R d C
p p
ROH Hemiketal ROH
27carbon
reactw reducingagents
inbasic
conditions
d
Hemiketal 20 ketal
Little in Acidic
27carbon
do notreactw reducingagents
conditions
Lially
useda'spittecting
groupsforcarbonyl

Alcohol as protecting group

RO OR
R H
1 Alcohol and C
Aldehyde OH Hemiacetal ROH
L'carbon PROTECTION Acetal Bearbon
reactw reducingagents do notreactw reducingagents
Liam DEPROTECTION LiAltly

by adding aqueous acid

RO OR
and
peforge ROH ROH C
Hemiketal
2 carbon
reactw reducingagents
PROTECTION petal
Little 2Bcarbon
DEPROTECTION do notreactw reducingagents

by adding aqueous acid Litem

Without protection Alcohol as a protectinggroup
Theketone's
carbonyl
O OH it was
reduced
was Not
protected
LiAlH4
Reduction

0 O OH

With protection protected

was
Redacted

0
Witted 0 HO OH O O O O protected

Prot
fogies H
LiAlH DÉÉotÉIon
cat Ht

O
O
were 910
protected
were
reduced
OH
ridiced
OH
 Phenol Ubiquinone
OH O
CH30 CH

930 H
0

Phenol Benzene Oxidation

Phylloquinone
2ry
oxidationHydroxy
Quinone
Mena
Quinone
Alcohol Ketone
OH 0
Oxidation I
mnemonic

NazCro
6 2 Quinone
Contains ketone
5 3
42504
OH O

p benzenediol 1,4 benzoquinone

a Hydroquinone conjugated ringsystem Resonance stabilized
Elecrophiles accept e s

Ubiquinone UbiQuinol

0 OH
CH30 CH30 CHz
Reduction

a H
my jacceptselectrons ago
0 OH
Electron donating
groups
COQ Ubiquinone CoQHz UbiQuinol
 Vitamin K I
Phylloquinone oxidation
HydroxyQuinone

MenaQuinone
Quinone

tie Vitamin K Phylloquinone natural Phytomenadione

MenaQuinone
EÉ IÉ Vitamin K FarnoQuinone fatsoluble
Phytonadione

Vitamin Kz NaphthaQuinone synthetic

watersoluble
Morepotent

less
MoreElecrophilic less flee rophilic reactive
because resonance stabilization
of
Quinones Hydroquinone HydroxyQuinone
mnemonic 2 OH groups 2 carbonyls t 3,1OHgroups
Quinone ketone
zryAlcohol
ketone Containsketone

OH O
0
I
1 OH
6 2
6 2

5 3
5 3
4
O
O OH
1,4 benzoquinone 2 Hydroxy 1,4
benzenediol
benzoquinone
p
a Hydroquinone
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