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SCH4U Organic Chemistry Cheat Sheet Cheat Sheet (DRAFT) by

Organic Chem nomenclature + Organic Chem Reactions Cheat Sheet

This is a draft cheat sheet. It is a work in progress and is not finished yet.

Root Name/B­ranch Prefixes

Number of C atoms / branches
Root prefix
Multip­lying prefix
1
meth-
mono-
2
eth-
di-
3
prop-
tri-
4
but-
tetra-
5
pent-
penta-
6
hex-
hexa-
7
hep-
hepta-
8
oct-
octa-
9
non-
nona-
10
dec-
deca-

Alkyl Groups

CH3
methyl
C2H5
ethyl
C3H7
propyk
C4H9
butyl
C5H11
pentyl
C6H13
hexyl
C7H15
heptyl
C8H17
octyle
C9H19
nonyl
C10H21
decyl

Alka­nes

CH4
Methane
C2H6
Ethane
C3H8
Propane
C4H10
Butane
C5H12
Pentane
C6H14
Hexane
C7H16
Heptane
C8H18
Octane
C9H20
Nonane
C10H22
Decane
General Formula for an alkane is C(n)H(­2n+2)
Alkanes are non-polar (only C-H bonds)

Common Functional Groups

F
Flouro
Cl
Chloro
Br
bromo
I
iodo
NO2
nitro
NH2
amino

Alkenes

General formula for alkenes is C(n)H(2n)
Alkenes contain a carbon to carbon double bond
Non-polar
Suffix if highest precedence is -ene

Alkynes

Alkynes have carbon­-carbon triple bonds
General formula for alkynes is C(n)H(­2n-2)
Non polar
suffix is -yne if highest precedence

Cyclic Aliphatics

Cyclic compounds occur when carbon atoms are arranged to form rings
General formula for cyclic compounds are: C2H2n (cyclo­alk­ane), C2H2n-2 (cyclo­alk­ene), C2H2n-4 (cyclo­alk­ane).
Non-Polar
Prefix is cyclo
 

Aromatic nomenc­lature

F
Flouro­benzene
Br
Bromob­enzene
Cl
Chloro­benzene
NO2
Nitrob­enzene
COOH
Benzoic acid
OH
Phenol­/hy­droxy benzene
NH2
anilin­e/a­min­obe­nzene
CH3
Toluen­e/m­eth­ylb­enzene
if 1,2 position
Ortho (o-)
if 1,3 position
Meta (m-)
if 1,4 position
Para (p-)
Aromatics hydroc­arbons are benzene or compounds containing a benzene ring.
Benzene has the chemical formula C6H6

Geometric Isomer­/St­ruc­tural Isomer

Structural Isomers are when compounds have the same chemical formula, but a different arrang­ement of atoms.

Geometric Isomers are isomers where atoms are arranged the same but have a different 3-d arrang­ement. Alkenes can form cis-trans isomers Alkenes can form cis-trans isomers.

Interm­ole­cular Forces

LDF
Very weak forces that exist in all atoms/­mol­ecules caused by instan­taneous dipoles, become stronger as molecule gets larger
Dipole­-Dipole
Strong attraction force between opposite charges of polar molecules
Hydrogen bonding
Very strong dipole­-dipole forces with H atoms covalently bonded with an N, O or F atom
 
(strength is in descending order)

Emprical and Molecular Formulas

n = m/MM
m = m x MM
E.F = simplest formula
M.F = MM actual/MM empirical formula

Functional Groups in descending order

Functional Group
Prefix
Suffix
Carboxylic Acid
  
-oic acid
Ester
  
[branc­h]-yl [root]­-oate
Amide
  
-amide
Aldehyde
formyl / oxo
-al
Ketone
oxo
-one
Alcohol
hydroxy
-ol
Amine
amino
-amine
Alkene­/Alkyne
  
-ene/-yne
Alkane
Ether
-oxy
Alkyl Halide
flouro­/ch­lor­o/b­rom­o/iodo
Note: for Alkene­/Al­kynes, to determine which takes higher priority, choose for which ever gives the better number combin­ation for side groups, if same then go alphab­eti­cally (ene > yne)

Functional Groups charac­ter­istics

Functional Group
Polarity
Solubility
B.P/M.P
Alkane
Non-Polar
Slightly Soluble
Depends on Length, more C = Higher, less C = Lower
Alkene
Non- Polar
Slightly Soluble
Depends on Length of parent C chain
Alkyne
Non-Polar
Slightly Soluble
Depends on Length of parent C chain
Cycloalkyl
Non-Polar
Slightly Soluble
Depends on Length of parent C chain
Alcohol
Polar
Very Soluble
Depends on Length of parent C chain
Aldehy­des­/Ketone
Polar
Very Soluble
Very High
Carboxylic Acids/­Esters
Polar
Very Soluble
Very High
Ethers
Polar
Very Soluble
Depends on Length of parent C chain
Amines­/Amides
Polar
Very Soluble
Depends on Length of parent C chain
 

Organic Reactions I

Combus­tio­n/C­omplete Oxidation
Adding Oxygen or Removing Hydrogen
Substi­tution
Replacing a hydrogen for a Halogen (Halog­ena­tion)
Addition of Alkanes
Breaking double bond by adding Halogen (Halog­ena­tion) , Hydrogen (Hydro­gen­ation), or Water (Hydra­tion)
Elimin­ation of Alkanes
The opposite of Addition
Mild Oxidation Reactions
Using Oxidizing agents to turn Primary alcohols into aldehy­des­/ca­rbo­xylic acids, and secondary alcohols into ketones.
Remember Markovniks Rule: "Rich get richer­"
Tertiary alcohols do not react in mild oxidation reactions

Benzene Reactions

Haloge­nation
Benzene + Halogen
Nitration (Dehyd­ration)
Benzene + HNO3 (in acidic condit­ions)
Alkylation
Benzene + Alkylh­alide

Organic Reactions II Reactions

Formation of Ethers (Conde­nsa­tio­n/D­ehy­dra­tion)
Alcohol + Alcohol --> Ether
Formation of Esters (Conde­nsa­tio­n/D­ehy­dra­tion)
Alcohol + Carboxylic Acid --> ester
Decomp­osition of Esters (Hydro­losis)
Ester --> Alcohol + Carboxylic Acid
Formation of Amides (Conde­nsa­tio­n/D­ehy­dra­tion)
Amine + Carboxylic Acid --> Amide + H2O
Decomp­osition of Amides (Hydro­losis)
Amide + H2O ---> Amine + Carboxylic Acid
Synthesis of Primary Amines (Subst­itu­tion)
Alkyl Halide + ammonia ---> Primary Amine
Synthesis of Secondary Amines (Subst­itu­tion)
Alkyl Halide + Primary Amine ---> Secondary Amine
Synthesis of Tertiary Amines (Subst­itu­tion)
Alkyl Halide + Secondary Amine ---> Tertiary Amine

Polymers

Large Molecule that are composed of many repeated subunits are called monomers
Created through polyme­riz­ation
Polyme­riz­ation (addition - chain reaction of alkene) CxHy + CxHy+ CxHy+ ... --> [CxHy]n
Polyme­riz­ation (conde­nsation with alcohol - polyester) HOCxHyOH + HOOCCx­HyCOOH + ... ---> [O2CCx­HyO­2Cx­HyO2]n
Polyme­riz­ation (conde­nsation with alcohol - polyamide) H2NCxHyNH2 + HOOCCx­HyCOOH + ... --> [NOCCx­HyO­2Cx­HyON]n
Polyme­riz­ation (conde­nsa­tion) need the
reacting functional groups to be on both
sides of the monomers to be able to
complete the chain reaction (-dioic acid, -
diol, -diamine)