1 ORGANIC CHEMISTRY 2 SUBSTITUENTS & FUNCTIONAL GROUPS

TYPES OF CARBON CHAIN PREFIXES

CARBON CHAINS 1 meth-

2 eth-
Alkane prop-
3
3 Carbons isopropyl
C C 4 but-

5 pent-
Alkene hex-
6
C C hept-
7

Alkyne 8 oct-

C C 9 non- 4 Carbons isobutyl

10 dec-

11 undec-
12 dodec-

COMMON SUBSTITUENTS
4 Carbons sec-butyl

1 Carbon methyl

5 Carbons neopentyl

2 Carbons ethyl
FUNCTIONAL GROUPS
Skeletal Structure Example
Name Structural Formula (Line Diagram)

3 Carbons propyl Alkene C C

Alkyne C C

4 Carbons butyl
Alkyl Halide R X
X

MELISSAMARIBEL.COM MELISSAMARIBEL.COM
3
FUNCTIONAL GROUPS 4 ALKENE REACTIONS
X
HX
Alcohol R OH Hydrohalogenation
OH
Markovnikov
HX = HCl, HBr, HI
O
Ether R O R'
HBr
Hydrohalogenation
O O Anti-Markovnikov ROOR
Epoxide (peroxide) Br
R C C

+ OH
O O H3O
Ketone Hydration
R C R'

O O
+
Aldehyde H3O OH
R C H Hydration
H (with rearrangement)
O O
Carboxylic Acid R C OH 1. Hg(OAc) 2 , H2O
OH Oxymercuration
O O - Demercuration 2. NaBH4
OH
Ester R C O R'
O
O 1. Hg(OAc) 2 , CH3 OH
O Alkoxymercuration
- Demercuration 2. NaBH4
Amide
R C NH 2 NH 2 OCH 3

OH
Amine R NH 2
NH 2 Hydroboration- 1. BH 3 , THF
Oxidation
2. H2O2 , OH -
R
Phenyl

MELISSAMARIBEL.COM MELISSAMARIBEL.COM
5 ALKENE REACTIONS 6 ALKENE REACTIONS
O
H2 1. O3
+
Catalytic Hydrogenation 2. (CH3 )2 S O
(Catalytic Reduction) Ozonolysis H
Pt or
(Reducing Conditions) 2. Zn/H2O

X
Halogenation X2
1. O3
(Addition of Halogens) Ozonolysis + O
CCl4 X (Oxidizing Conditions) 2. H2 O 2
Anti-Addition O
OH
OCH3
CH3 OH KMnO4 (hot)
Addition of Alcohol + O
Oxidative Cleavage H 3O
+
H+ O
OH
X
X2
Halohydrin Formation
H2 O FREE RADICAL HALOGENATION
OH

O Br
NBS
Epoxidation R C O OH O Allylic Bromination
light or heat Br
or peroxide
or mCPBA

OH NBS
mCPBA Benzylic Bromination
Anti-Hydroxylation light or heat
+ or peroxide
H3O
OH
Free Radical Br2
OH
1. OsO4 OH Bromination light or heat Br
Syn-Hydroxylation
( 2 types) 2. H2O2
Cl
OH
KMnO4 OH Free Radical Cl 2 Cl
Chlorination +
(cold, dilute) light or heat

MELISSAMARIBEL.COM MELISSAMARIBEL.COM
7 ALKYNE REACTIONS 8 ALKYNE REACTIONS
H2
Catalytic Hydrogenation
(Catalytic Reduction) Pd/C

O3
+
O
C
O

O
Ozonolysis H2O OH
H2
Reduction to (2 Examples)
cis-alkene Lindlar's OH
O3
+

O
O
H2O OH
Na or Li
Reduction to
NH 3 (l) O
trans-alkene
Permanganate KMnO4
Oxidation
H 2O O
Neutral
X X
HX
Hydrohalogenation
excess O O
Permanganate 1. KMnO4 , OH -
+
Oxidation
2. H+ HO OH
O Basic
Hydration HgSO4
X X
Markovnikov X2
H2 SO4 Halogenation
excess
X X
1. Sia2BH THF H
Hydration
Anti-Markovnikov
2. H2O2 , OH-, H2O
O

Hydration H2SO4
+
of an or
Internal Alkyne 1. Sia2BH THF O
2. H2 O , OH-, H2O
2

MELISSAMARIBEL.COM MELISSAMARIBEL.COM
9 ALCOHOL REACTIONS 10 ALCOHOL REACTIONS
Conversion OH I OH Na2Cr2 O7 OH
HI
Chromic Acid Oxidation
to Alkyl o
of 1 Alcohol H2SO4
Iodide O

OH PCC H
OH Br PCC Oxidation of
HBr 1 o Alcohol
Conversion
to Alkyl
O

Bromide
(2 ways) H Na2 Cr2 O7 OH
OH
Br Chromic Acid Oxidation
PBr 3 of Aldehyde H2 SO4
O O

OH O
OH Cl Chromic Acid Oxidation Na2Cr2 O7
o
HCl of 2 Alcohol
H2 SO4
ZnCl2
Conversion
to Alkyl OH O
Chloride Cl PCC
OH PCC Oxidation of
(2 ways) SOCl2
2o Alcohol

ETHER REACTIONS
OH OTs
Conversion TsCl Williamson NaH Br
to tosylate Ether
ester Synthesis OH or Na O- O
or K

OH H2 SO4 excess
Acid-catalyzed Acid-Catalyzed +
Dehydration
or Cleavage O HX X X
H3 PO4

MELISSAMARIBEL.COM MELISSAMARIBEL.COM
11 BENZENE REACTIONS 12
REDUCTION REACTIONS
NO 2 OH
HNO 3 O NaBH4
Nitration
H2 SO4
EtOH
Ketone to
SO 3H 2 o Alcohol
OH
SO 3 O LiAlH4
Sulfonation
H2SO4
H3 O+

Cl
O OH
Cl2
Chlorination NaBH4
AlCl 3
H EtOH
Aldehyde to
Br OH
1 o Alcohol O
Br2 LiAlH4
Bromination
FeBr3 +
H H3O

O
Friedel-Crafts Cl NaBH4
Alkylation AlCl 3
EtOH OH
Acid Chloride to Cl
Cl 1 o Alcohol
O
Friedel-Crafts Alkylation LiAlH4
(with rearrangement) AlCl 3 +
Cl H3O OH

O O
O
LiAlH4
Ester to
Friedel-Crafts Cl +
Two Alcohols +
Acylation O H3O OH HO
AlCl 3

MELISSAMARIBEL.COM MELISSAMARIBEL.COM
13
REDUCTION REACTIONS
O
Carboxylic Acid LiAlH4
o
to a 1 Alcohol +
OH H3O OH

O
LiAlH4
Amide to
Amine H3O
+
NH2
NH2

O O
DIBALH
Ester to Aldehyde
using DIBALH H2 O
O H

O
Br2 NH2
Hoffman Rearrangment
(Amide to Amine) OH -
NH2

MELISSAMARIBEL.COM
 CHEMISTRY I
MELISSAMARIBEL COM

1•
36

FORMULA SHEET
ATOMIC STRUCTURE PERCENT ABUNDANCE

Atomic Number Protons Electrons Average Atomic Mass x mass x mass

Charge Atomic Number Electrons

Mass Number Protons Neutrons

ISOTOPE NOTATION NAMING COVALENT MOLECULAR

COMPOUNDS PREFIXES

A
X
1 mono

Z 2 di
A Mass Number
Z Atomic Number 3 tri

X Chemical Symbol
4 tetra

COMMON POLYATOMIC IONS

penta
5
NH4 Ammonium NO 3 Nitrate
6 hexa
OH Hydroxide NO 2 Nitrite

2
CN Cyanide CO 3 Carbonate 7 hepta
2
C2H 3O 2 Acetate CrO 4 Chromate
8 octa
2
BrO3 Bromate Cr2 O 7 Dichromate

IO 3 2 9 nona
Iodate SO4 Sulfate
2
ClO4 Perchlorate SO3 Sulfite 10 deca

3
ClO 3 Chlorate PO4 Phosphate

3
ClO Chlorite PO3 Phosphite
2

ClO Hypochlorite
MELISSAMARIBEL COM MELISSAMARIBEL COM

THE METRIC SYSTEM 37

2• 38
3•
.

Name Symbol Number TEMPERATURE

DENSITY
Tera T 12
10 Kelvin to Celsius: Celsius to Kelvin:
9 Mass C K 273 K C 273
Giga G 10 Density
Volume
Mega M 106
Kilo k 103 Celsius to Fahrenheit: Fahrenheit to Celsius:
Common Units: g mL
Hecto h
2 F 18x C 32 C 0 56 F 32
10
3
1 g cm
Deka da 10
1
Deci d 10 THERMOCHEMISTRY
Centi 2
c 10
3 Specific Heat Capacity Specific Heat Capacity of Water Heat Capacity
Milli m 10

Micro µ 10
6 q mC T C water 4 184 J g C q C T
9
Nano n 10 Internal Energy Work Bomb Calorimetry
p 12
Pico 10
15
E q w or U q w w P V qcal C cal T
Femto f 10
q q
rxn cal

DIMENSIONAL ANALYSIS q
rxn
E mol
Length Mass Volume Time
3 Coffee Cup Calorimetry
1 in 2 54 cm 1 kg 2 205 lb 1 mL 1 cm 1 min 60 sec
q q
1 mi 1 609 km 1 lb 453 6 g 1L 1 057 qt 1 hour 60 min metal water

1m 1 0936 yd 1 oz 28 3495 g 1 tbsp 14 787 mL 1 hour 3600 sec Formula Expanded

mmetal x C metal x T metal m water x Cwater x T water
1 mi 1609 3 m 1 gal 4 qt
1 ft 12 in 1L 1 dm3
3 ENERGY CONVERSION FACTORS
1 ft 28 317 L

1 calorie cal 1 cal 4 184 J

PERCENT ERROR
1 kilocalorie kcal 1 kcal 4184 J
Percent Error actual value experimental value x 100 6
1 kilowatt hour kWh 1 kWh 3 60 x 10 J
actual value
1 kilojoule kJ 1 kJ 1000 J
PERCENT YIELD
actual yield
Percent Yield x 100
theoretical yield
MELISSAMARIBEL COM MELISSAMARIBEL COM
39
4q
.

OXIDATION NUMBERS
40
5•
ENTHALPY BOHR S MODEL
18 Type Example Oxidation number
Standard Enthalpy of Formation E 2 179 x 10 J 1 1
ni2 n2f
H n Hf products
n Hf reactants

Bond Energy RYDBERG S FORMULA

7 1 1 1
H n Hreactants n H products 1 1 09737 x 10 m
λ hc ni2 nf2

ELECTROMAGNETIC SPECTRUM ELECTROMAGNETIC SPECTRUM

CONSTANTS
c hc
ⱱ E 8 8
λ λ c 2 998 x 10 m s or 3 0 x 10 m s

h 34
λ mv E hⱱ h 6 626 x 10 J s

c 2
c concentration mol L kgm
n 1J 1
V V volume L s2
E given
FORMAL CHARGES
Number of Photons
E photon

Formal Charge Valence Electrons Bonding Electrons Individual Electrons

QUANTUM NUMBERS
BOND ORDER
Principal n Angular Momentum l Magnetic ml Spin m s

Size Energy of Orbital Orbital Shape Orbital Orientation Spin of electron

Bonding electrons Antibonding electrons
l 0 1 2 3 ml l to l ms 1 2 Bond Order
n 1 2 3 2

Angular Momentum l
ELECTRON GROUPS
s l 0
Electron Groups bonds lone pairs
p l 1

d l 2

f l 3
MELISSAMARIBEL COM MELISSAMARIBEL COM
41
6•i 42
7•
ELECTRON GEOMETRY MOLECULAR GEOMETRY
ELECTRON GROUPS ELECTRON GEOMETRY

2 Linear

Trigonal Planar
3

4 Tetrahedral

5 Trigonal Bipyramidal

6 Octahedral

HYBRIDIZATION

ELECTRON GROUPS ELECTRON GEOMETRY HYBRIDIZATION

2 Linear sp

Trigonal Planar
sp 2
3

4 Tetrahedral sp 3

5 Trigonal Bipyramidal sp3d

3
6 Octahedral sp d 2
MELISSAMARIBEL COM MELISSAMARIBEL COM

.
Bae43
8
BOYLE S LAW GAY LUSSAC S LAW
44
9
%

MOLARITY DILUTIONS P1 P2
P1 V1 P2 V2
M 1V 1 M2V2
mol of solute T1 T2
Molarity M or
L of solution C 1 V1 C2 V2
CHARLES S LAW VAN DER WAALS

MOLALITY MASS PERCENT COMPOSITION

V1 V2 n2 a
P x V nb nRT
mol of solute mass of element T1 T2 V2
Molality m Mass x 100
kg of solvent mass of compound

COMBINED GAS LAW AVOGADRO S LAW

PERCENT BY VOLUME PERCENT BY MASS P1 V1 P2 V2 V1 V2

Volume of solute mass of solute T1 T2 n1 n2

v v x 100 m m x 100
Volume of solution mass of solution

IDEAL GAS LAW GAS CONSTANTS

L atm
PERCENT BY MASS VOLUME PARTS PER MILLION PPM R 0 08206
mol K
PV nRT
grams of solute mass of solute
m v 6 L atm
x 100 ppm x 10 0 0821
mL of solution mass of solution mol K

PARTS PER BILLION PPB PRESSURE UNITS CONVERSIONS STANDARD TEMPERATURE

PRESSURE STP
mass of solute 9 1 atm 760 torr
ppb x 10 Pressure 1 atm
mass of solution 1 atm 760 mmHg
Temperature 273 K
1 atm 101300 Pa
Volume 22 4 L mol
1 atm 101 3 kPa
1 atm 14 7 psi
MELISSAMARIBEL COM MELISSAMARIBEL COM
45
10
Akka 11
46
Be
UNIT CELLS
RATE OF EFFUSION AVERAGE KINETIC
ENERGY
SIMPLE CUBIC ATOMS PER CELL: 1 l 2r
Rate of Effusion A MB
3
Rate of Effusion B MA KE avg 2
RT
4r
BODY CENTERED CUBIC ATOMS PER CELL: 2 l
3
BCC
ROOT MEAN SQUARE BRAGG EQUATION
VELOCITY
FACE CENTERED CUBIC
3RT n 2dsin ATOMS PER CELL: 4 l 2r 2
u rms FCC
m

HYDROSTATIC PRESSURE DALTON S LAW

FREEZING POINT DEPRESSION BOILING POINT ELEVATION

p h g PTotal PA PB PC Kf m Tb K bm
Tf

CLAUSIUS CLAPEYRON EQUATION PARTIAL PRESSURE RAOULT S LAW HEATING CURVE FORMULAS

P2 Hvap 1 1
ln PA XA PTotal Psolution
o q mC T
P1 R T1 T2 Xsolvent P solvent

Hvap q n Hfusion
ln P ln A PA XA P o
A
RT MOLE FRACTION q n H vap
Hvap
moles of gas A
P Ae RT XA OSMOTIC PRESSURE HENRY S LAW
total moles in gas mixture

CAPILLARY RISE MRT C g kP g

2Tcos
h
r g
MELISSAMARIBEL COM
CHEMISTRY II 47
1
an
.
MELISSAMARIBEL COM
48
2•
FORMULA SHEET
ANIONIC LIGANDS NEUTRAL LIGANDS
Symbol Name Symbol Name

KINETICS F fluoro H2O aqua

Zero Order First Order Second Order Cl chloro NH3 ammine

Br bromo CO carbonyl
rate law rate k rate k A rate k A 2
I iodo NO nitrosyl
CN cyano py pyridyl

NO 3 nitrato en ethylenediamine
1 1 1
Units of rate constant Ms s M s1 OH hydroxo

O2 oxo
2
C 2 O4 oxalato
1 1 2 carbonato
integrated rate law A t kt A 0 ln A kt ln A kt CO 3
t 0 A t A 0
MONODENTATE LIGANDS POLYDENTATE LIGANDS
PREFIXES PREFIXES
Relationship between 2 di 2 bis
slope and rate k slope k slope k slope
constant k
3 tri 3 tris

A 0 693 1 4 tetra 4 tetrakis

t 0 t1 t1
half life 1 2 2 2
2k k A 0 k
5 penta pentakis
5
RATE OF REACTION
6 hexa 6 hexakis
change in concentration of product product
rate of appearance
time interval t
METAL NAMES
change in concentration of reactant reactant Metal Anion Name
Ion Cation Name Anion Name
rate of disappearance copper cuprate
time interval t
Co3 cobalt III cobaltate III
gold aurate
Pt 2 platinum II platinate II iron ferrate
ARRHENIUS EQUATION VARIATIONS lead plumbate
Cu copper I cuprate I
tin stannate
Ea Ea 1 k1 Ea 1 1 Fe 3 iron III ferrate III manganese manganate
RT ln k ln A ln nickel nickelate
k Ae T k2 R T2 T1 Ag silver I argentate I
R zinc zincate
chromium chromate
MELISSAMARIBEL COM MELISSAMARIBEL COM
49
3• EQUILIBRIUM
50
4
⑨
SPECTROCHEMICAL SERIES

CN Strongest hc
oct E coefficient K Q Favors Reactants
λ products
NO 2 Reaction Quotient Qc coefficient
reactants K Q At Equilibrium
en
concentration
K Q Favors Products
NH 3
8
C 2 O4
2 c
8
2 998 x 10 m s or 3 0 x 10 m s P x
product
Reaction Quotient Q p
H2O
34
x coefficient Preactant
x

F h 6 626 x 10 J s pressure

Cl
Br K 1 Favors Reactants

I Weakest K 1 At Equilibrium

K 1 Favors Products
coefficient
products
Equilibrium Constant K c
Red reactants
coefficient

620 700 nm
concentration
x
Pproduct
O r7 6 2 0
m

Equilibrium Constant Kp
59
let

Q K sp Forms Precipitate
5n

x
x coefficient Preactant
a n nm
Vio

Q Ksp No Precipitate Forms

45

pressure
ge
0
40
45

nm

n
Kp Kc RT R 0 0821
5
Blu

w
7
49

59
llo
2n
e

P MRT n moles of products moles of reactants

Ye
57
m

492 577 nm
Green
MELISSAMARIBEL COM MELISSAMARIBEL COM

ACIDS BASES
H
51
5 52
6•
STRONG ACIDS LIST
pH log H pOH log OH Chemical Formula Name Dissociation

HCl Hydrochloric acid HCl H Cl

pH pOH HBr Hydrobromic acid HBr H Br

H 10 OH 10
HI Hydroiodic acid HI H I

HClO4 Perchloric acid HClO4 H ClO4

pH pOH 14 H x OH 1 x 10
14 HClO3 Chloric acid HClO 3 H ClO 3
2
H2 SO4 Sulfuric acid H 2 SO4 2H SO 4

HNO 3 Nitric acid HNO 3 H NO3

pH Ion Concentration
H 3O OH
pH 7 More acid than base
Acidic H 3O 1 0 x 10 7
WEAK ACIDS LIST
Chemical Formula Name Dissociation
pH 0 6
7
OH 1 0 x 10 HNO2 Nitrous acid HNO 2 H NO 2

H2 SO3 Sulfurous acid H 2 SO3 H HSO 3

pH Ion Concentration
H 3O OH
HClO2 Chlorous acid HClO 2 H ClO 2
Neutral pH 7
Equal amounts of acid and base
H 3O 1 0 x 10
7 HClO Hypochlorous acid HClO H ClO

OH 1 0 x 10
7 HC2 H 3 O 2 Acetic acid HC2 H 3 O 2 H C 2 H 3O 2

H2 CO 3 Carbonic acid H 2CO 3 H HCO3

pH Ion Concentration
H3 PO4 Phosphoric acid H 3PO4 H H2 PO4
H 3O OH
pH 7 HF -
Hydrofluoric acid
Basic
More base than acid HF H F
H 3O 1 0 x 10
7
-
H2S Hydrosulfuric acid H2 S H HS
pH 8 14
CN -
7
OH 1 0 x 10
HCN Hydrocyanic acid HCN H
HCOOH -
Formic acid HCOOH H HCOO
MELISSAMARIBEL COM MELISSAMARIBEL COM
53
7
am 54
8
BB

DISSOCIATION CONSTANTS
STRONG BASES LIST
Chemical Formula Name Dissociation H 3O A HB OH
Ka Kb
LiOH lithium hydroxide LiOH Li OH HA B

NaOH sodium hydroxide NaOH Na OH

KOH potassium hydroxide KOH K OH
Ka x Kb 1 0 x 10 14 K Ka x K b
RbOH rubidium hydroxide RbOH Rb OH

CsOH cesium hydroxide CsOH Cs OH

calcium hydroxide Ca OH 2 Ca2 2 OH pK a pKb

Ca OH 2
Sr OH 2 strontium hydroxide Sr OH 2 Sr 2 2 OH pKa log K a pKb log K b

Ba OH 2 barium hydroxide Ba OH 2 Ba2 2 OH

PERCENT IONIZATION

WEAK BASES LIST H3 O eq

ionization x 100
Chemical Formula Name Dissociation HA 0
NH 3 Ammonia NH3 H 2 O NH 4 OH
HENDERSON HASSELBALCH EQUATION
C 6 H 5 NH 2 Aniline C 6 H5 NH2 H2O C 6 H 5 NH 3 OH
CH 3 NH2 Methylamine CH 3NH2 H 2O CH 3 NH 3 OH
A
C 5H 5 N Pyridine C 5H5N H2 O C5 H 5NH OH pH pK a log
HA
MELISSAMARIBEL COM MELISSAMARIBEL COM

55
9• 56
10
Mlk
INDICATORS ENTROPY S

S universe S system S surroundings

qsurr H
S univ S sys S univ S sys
T T

So nS o298 products nS o298 reactants

Wf
S k ln W S k ln
Wi

k 1 38 x 10 23 J K W microstate

pH SECOND LAW OF THERMODYNAMICS

S universe 0 Spontaneous

S universe 0 Nonspontaneous

S universe 0 At Equilibrium
MELISSAMARIBEL COM MELISSAMARIBEL COM
57
11
Mhk
ELECTROCHEMISTRY 58
12
ma
ENTHALPY H
E ocell Eocathode o o RT ln K
Eanode Ecell
nF
Ho nH o298 products nH o298 reactants

GIBBS FREE ENERGY G Eocell 0 0592 V log K Eocell

0 0257 V
ln K
n n

Go nG o298 products nGo298 reactants

0 0257 V 0 0592 V
E cell Eocell ln Q E cell Eocell log Q
n n

G Go RT ln K Go RT ln K G Go RT ln Q
wmax qEocell o RT ln Q
E cell E cell
nF

o
G H T S Go H T So
wmax o
nFE cell Go o
nFEcell

SPONTANEITY FREE ENERGY

H S Low Temperature High Temperature Go RT lnK G nFE cell

Spontaneous G 0 Spontaneous G 0
Nonspontaneous G 0 Nonspontaneous G 0
Q nxF
Spontaneous G 0 Nonspontaneous G 0 or Anode Cathode
Q I xt
Nonspontaneous G 0 Spontaneous G 0
UNITS
J C
F 9 648 x 104 F 9 648 x 104
V mol mol

J C 96500 C
V C A s F
mol e
MELISSAMARIBEL COM
59
13
me

NUCLEAR CHEMISTRY

E mc 2 1 eV 1 602 x 10 19 J

HALF LIFE

0 693 t t 1 ln Nt
t1 Nt N0 e
2
N0

# of protons x 1 0073 amu # of neutrons x 1 0087 amu # of electrons x 0 00055

amu

A A 4
ALPHA DECAY Z
X 4
2
He Z 2
Y

A 0 A
BETA DECAY Z
X 1 e Z 1
Y

A 0 A
GAMMA DECAY Z
X* 0 Z
X

A 0 A
POSITRON EMISSION Z
X e
1 Z 1
Y

A 0 A
ELECTRON CAPTURE Z
X e
1
Y
Z 1