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Gr. 12 Organic Chemistry Cheat Sheet by

Introd­uction

The term organic generally means "­som­ething made from the earth" or "not chemically synthe­siz­ed."­
Organic chemistry refers to the study of compounds that contain carbon atoms as the principal element.
The simplest organic compounds are hydroc­arbons made from C and H atoms
Despite the term organic generally meaning "­nat­ura­l," organic compounds can in fact be chemically synthe­sized (first synthe­sized organic compound was urea - found in mammal urine)
Carbon has a bonding capacity of 4 so each C atom must always make 4 bonds within a compound

General Nomenc­lature

Usual follows order prefix + root + suffix
Prefix
Indicates name/m­ult­iplying prefix­es/­pos­ition of branches
Root
Indicates number of carbons in the parent chain
Suffix
Indicates the parent chain's functional group

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-
Special nomenc­lature prefixes: See Importance of Functional Groups, Haloal­kyl­/Other Functional Groups, and Special Alkyl Branches

All prefixes are listed in alpha order when writing the name of an organic compound, except for cyclo- and iso-.

Importance of Functional Groups

Functional Group
Suffix if Highest Precedence
Prefix if Lower Precedence
RC(=O)OH (carbo­xylic acid)
-oic acid 2
carboxy-
RC(=O)OR' (ester)
[branch]1-yl [root]1-oate
alkoxy­car­bonyl-
-amide
carbamoyl-
RC≡N (nitrile)
-nitrile
cyano-
RC=O (aldehyde)
-al 3
oxo-3
RC(=O)R' (ketone)
-one
oxo-
R(OH)R' (alcohol)
-ol
hydroxy-
-amine
amino-
RC=CR' (alkene)
-ene 4
Always used as a suffix
RC≡CR' (alkyne)
-yne 4
Always used as a suffix
RCCR' (alkane)
-ane
Always used as a suffix
R(X)R'
Always used as a prefix
See Haloal­kyl­s/Other Functional Groups
[1][branch] and [root] refer to the length of the carbon group's prefix (meth-, eth-, prop-, etc.)
[2]If the carbon in the RCOOH group is not the parent chain, the highest precedence suffix is -carboxylic acid
[3]If the carbon in the RCO group is not the parent chain, the highest precedence suffix is -carbal­dehyde, and the alternate prefix is formyl-
[4]If a compound is both an alkene and an alkyne, both -ene and -yne are used

Haloal­kyl­s/Other Functional Groups

Functional Group
Prefix
R-O-R' (ether)1
[branch]-oxy-
R-C-R (cyclo­alkyls)
cyclo-
fluoro-
bromo-
chloro-
iodo-
nitro-
ortho-[bran­ch(es)]
meta-[bran­ch(es)]
para-[bran­ch(es)]
[1]Ethers take precedence in prefixes over all other prefixes, except the branches attached to the ether group
[2]Applies only to benzene ring branches

Special Alkyl Branches

Propyl
Butyl
n-propyl (normal)
n-butyl (normal)
isopropyl (y-shape)
isobutyl (y-shape)
 
sec-butyl (2
nd
 C)
 
tert-butyl (t-shape)
 

Alkanes

Contain only single bonds between C atoms
General chemical formula
C
n
H
2n+2
(n = whole number)
Odour
Odourless
Polarity
Non-polar (only C-H bonds)
Solubility in water
Slightly soluble
Boilin­g/m­elting point
Depends on length of parent C chain (more C = BP, less C = BP)

Alkenes

Contain at least one double bond between C atoms
General chemical formula
C
n
H
2n
(n = whole number)
Odour
Almost odourless
Polarity
Non-polar (only C-H bonds)
Solubility in water
Slightly soluble
Boilin­g/m­elting point
Depends on length of parent C chain (more C = BP, less C = BP)

Alkynes

Contain at least one triple bond between C atoms
General chemical formula
C
n
H
2n-2
(n = whole number)
Odour
Almost odourless
Polarity
Non-polar (only C-H bonds)
Solubility in water
Slightly soluble
Boilin­g/m­elting point
Depends on length of parent C chain (more C = BP, less C = BP)

Cycloalkyl

Alkane­/al­ken­e/a­lkyne where the C atoms are joined in a ring shape
General chemical formula
C
2
H
2n
(cycloalkane)
C
2
H
2n-2
(cycloalkene)
C
2
H
2n-4
(cycloalkyne)
(n = whole number)
Odour
Odourless/almost odourless
Polarity
Non-polar (only C-H bonds)
Solubility in water
Slightly soluble
Boilin­g/m­elting point
Depends on length of parent C chain (more C = BP, less C = BP)

Alcohols

Any compound that contains a hydroxyl (R(-OH­)-R') group
General chemical formula
C
n
H
2n-1
OH (n = whole number)
Odour
Slightly pungent
Polarity
Polar (between O-H bonds); longer C chains decrease in polarity
Solubility in water
Very soluble; longer C chains decrease solubility
Boilin­g/m­elting point
Depends on length of parent C chain (more C = BP, less C = BP)

Aldehy­des­/Ke­tones

Any compound that contains a carbonyl (R-C(=­O)-R') group
Aldehydes have the carbonyl group at the first and/or last C atom of the molecule
Ketones have the carbonyl group in the middle C atom(s) of the molecule
General chemical formula
C
n
H
2n
O (n = whole number)
Odour
Pungent (aldehyde)
Sweet (ketone)
Polarity
Polar (between C=O bonds); longer C chains decrease polarity
Solubility in water
Very soluble; longer C chains decrease solubility
Boilin­g/m­elting point
Very high, increases with length of parent C chain (more C = BP, less C = BP)

Carboxylic Acids/­Esters

Any compound that contains a carboxyl (R-C(=­O)-­O-R') group
Carboxylic acids have the carboxyl group at the first and/or last C atom of the molecule
Esters have the carboxyl group in the middle C atom(s) of the molecule
General chemical formula
C
n
H
2n
COOH (n = whole number)
Odour
Unpleasant (carbo­xylic acid)
Pleasant (ester)
Polarity
Polar (between C=O bonds); longer C chains decrease polarity
Solubility in water
Very soluble; longer C chains decrease solubility
Boilin­g/m­elting point
Very high, increases with length of parent C chain (more C = BP, less C = BP)

Ethers

Any compound that contains an alkoxy (R-O-R') group
General chemical formula
C
n
H
2n+2
O (n = whole number)
Odour
Slightly pungent
Polarity
Polar (between C-O bonds); longer C chains decrease polarity
Solubility in water
Very soluble; longer C chains decrease solubility
Boilin­g/m­elting point
Depends on length of parent C chain (more C = BP, less C = BP)

Amines­/Amides

Any compound that contains a N atom in a carboxyl or carbonyl group
Amines have N atoms in a carbonyl group(s) (R-C(-­N(-­R')­-R")­-R'­")
Amides have N atoms in a carboxyl group(s) (R-C(=­O)-­N(-­R')­-R")
General chemical formula
C
n
H
2n-1
NO (n = whole number)
Polarity
Polar (between C=O, C-O and C-N bonds); longer C chains decrease polarity
Solubility in water
Very soluble; longer C chains decrease solubility
State @ SATP
Depends on length of parent C chain (more C = more solid, less C = more gas)
 

Interm­ole­cular Forces (IMFs)

Forces that occur between molecules
Influence the physical properties of a substance
Weaker than intramolecular forces (forces within molecules)
3 main types:
London Dispersion Forces (LDF)
Very weak forces that exist in all atoms/­mol­ecules caused by temporary charges due to e¯ shifts; become stronger with more e¯
Dipole- Dipole
Attraction between opposite charges of polar molecules;
main reason for difference in meltin­g/b­oiling points
Hydrogen bonding
Strong dipole­-dipole forces with H atoms covalently bonded with an N, O or F atom
Strength of forces: (weakest) LDF Dipole­-dipole H-bonding (stron­gest)

Combustion Reactions

All hydroc­arbons burn with oxygen gas (alkan­es/­alk­ene­s/a­lky­nes­/al­cohols)
Combustion of hydroc­arbon
C
x
H
y
+ O
2
CO
2
+ H
2
O
Combustion of alcohol
C
x
H
y
OH + O
2
CO
2
+ H
2
O

Elimin­ation Reactions

Take away 2 atoms to form double bond or H
2
O
Also called conden­sat­ion­/de­hyd­ration reactions
Elimin­ation of haloalkyl
C
x
H
y
X
z
+ [strong base] C
x
H
y-1
+ [halogen (X) salt] + H
2
O
Elimin­ation of alcohol
C
x
H
y
OH [conc acid] C
x
H
y-1
+ H
2
O

Substi­tution Reactions

Replace one atom with another
Substi­tution reaction
C
x
H
y
+ X
2
[heat/­pre­ssure] C
x
H
y-1
X + HX
Benzene rings
Benzene does not have true double bonds, so only substi­tution reactions can be performed
Benzene substi­tution
C
6
H
6
+ X
2
C
6
H
5
X + HX
Benzene halide substi­tution
C
6
H
5
X + X
2
C
6
H
4
X
2
+ HX
Halogen in benzene halide reactions forms product meta position only (1,3-[­X]b­enzene)

Addition Reactions

Add atoms across double­/triple bond
Alkene­s/a­lkynes are nucleo­philes (they like to give up e_)
Hydroh­alo­gen­ation
C
x
H
y
+ HX C
x
H
y+1
X
Haloge­nation
C
x
H
y
+ X
2
C
x
H
y
X
2
Hydrog­enation
C
x
H
y
+ H
2
C
x
H
y+2
Hydration
C
x
H
y
+ H
2
O
C
x
H
y+1
OH
Markov­nikov's Rule: "the rich get richer­"
The H atom of water/­hyd­rogen gas/hy­drogen halide will always bond with the C atom that already had more H atoms bonded to it in an addition reaction

Redox Reactions

Oxidation
C atoms will form more bonds to O atoms
Occurs when an organic compound reacts with an oxidizing agent (usually KMnO
4
/K
2
Cr
2
O
7
)
Oxidation of primary alcohol
C
x
H
y
OH [O] C
x
H
y-1
O (aldehyde)
Oxidation of secondary alcohol
C
x
H
y
OH [O] C
x
H
y-1
O (ketone)
Oxidation of tertiary alcohol
C
x
H
y
OH [O] NO RXN
Oxidation of aldehyde
C
x
H
y
O + H
2
O [O] C
x
H
y-1
OH + H
2
(carboxylic acid)
Reduction
C atoms will form fewer bonds to O atoms
Occurs when an organic compound reacts with an reducing agent (usually H
2
/LiAlH
4
)
Hydrog­enation (reduction of aldehyde)
C
x
H
y
O + H
2
[H] C
x
H
y+1
OH (primary alcohol)
Hydrog­enation (reduction of ketone)
C
x
H
y
O + H
2
[H] C
x
H
y+1
OH (secondary alcohol)

Esterification/Hydrolysis of Esters

Esteri­fic­ation
Conden­sation reaction (forms H
2
O)
Catalyzed by concen­trated H
2
SO
4
 and high heat
Esteri­fic­ation
C
x
H
y
COOH + C
x
H
y
OH [H
2
SO
4
] C
2x
H
2y
CO
2
+ H
2
O
Hydrolysis of Esters
Reverse reaction to esteri­fic­ation
Hydro = water, lysis = break
Hydrolysis of ester
C
2x
H
2y
CO
2
+ H
2
O [H
2
SO
4
] C
x
H
y
COOH + C
x
H
y
OH
Remember: Ester is a party girl; she drank some alcohol and did some acid

Synthe­sis­/Hy­dro­lysis of Amides

Synthesis of Amides
Conden­sation reaction (forms H
2
O)
Synthesis of amide
C
x
H
y
COOH (carbo­xylic acid) + C
x
H
y
NH
2
(amine) C
x
H
y
ONH
2
(amide) + H
2
O
Hydrolysis of Amides
Reverse reaction to synthesis
Hydrolysis of amide
C
x
H
y
ONH
2
(amide) + H
2
O C
x
H
y
COOH (carbo­xylic acid) + C
x
H
y
NH
2
(amine)

Synthesis of Amines

Amines can be made from haloalkyls using ammonia as a starting reactant
Synthesis of primary amines
C
x
H
x
X + NH
3
C
x
H
y
NH
2
+ HX
Synthesis of secondary amines
C
x
H
x
X + C
x
H
y
NH
2
C
2x
H
2y
NH + HX
Synthesis of tertiary amines
C
x
H
x
X + C
2x
H
2y
NH C
3x
H
3y
N + HX

Polymers

Large molecules that are composed of many repeated subunits called monomers
Created through polyme­riz­ation
Examples include plastics, DNA, and proteins
Unique physical properties - checmi­cally unreactive, flexible/mouldable/stretc­hable
Polyme­riz­ation (addition - chain reaction of alkene)
C
x
H
y
+ C
x
H
y
+ C
x
H
y
+ ... [C
x
H
y
]
n
Polyme­riz­ation (conde­nsation with alcohol - polyester)
HOC
x
H
y
OH + HOOCC
x
H
y
COOH + ... [O
2
CC
x
H
y
O
2
C
x
H
y
O
2
]
n
Polyme­riz­ation (conde­nsation with alcohol - polyamide)
H
2
NC
x
H
y
NH
2
+ HOOCC
x
H
y
COOH + ... [NOCC
x
H
y
O
2
C
x
H
y
ON]
n
Polyme­riz­ation (conde­nsa­tion) need the reacting functional group(s) to be on both sides of the monomer(s) to be able to complete the chain reaction (-dioic acid, -diol, -diamine)
                           
 

Metadata

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  • Published: 23rd January, 2018
  • Last Updated: 29th December, 2018
  • Rated: 5 out of 5 stars based on 6 ratings

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