Gr.

12 Organic Chemistry Cheat Sheet

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 Introd​uction  Root Name/B​ranch Prefixes (cont)  Importance of Functional Groups (cont)

The term organic generally means "​som​‐ 9 non- nona- RCCR' - ane Always used as a
ething made from the earth" or "not 10 dec- deca- (alkane) suffix
chemically synthe​siz​ed."​ R(X)R' Always See Haloal​kyl​‐
Special nomenc​lature prefixes: See
Organic chemistry refers to the study of used as a s/Other Functional
Importance of Functional Groups, Haloal​‐
compounds that contain carbon atoms as prefix Groups
kyl​/Other Functional Groups, and Special
the principal element. [1]
Alkyl Branches [branch] and [root] refer to the length of
The simplest organic compounds are the carbon group's prefix (meth-, eth-, prop-
hydroc​arbons made from C and H atoms All prefixes are listed in alpha order when , etc.)
[2]
Despite the term organic generally meaning writing the name of an organic compound, If the carbon in the RCOOH group is not
"​nat​ura​l," organic compounds can in fact be except for cyclo- and iso- . the parent chain, the highest precedence
chemically synthe​sized (first synthe​sized suffix is -carboxylic acid
[3]
organic compound was urea - found in  Importance of Functional Groups If the carbon in the RCO group is not the
mammal urine) parent chain, the highest precedence suffix
Functional Suffix if Prefix if
is - carbal​dehyde, and the alternate prefix is
Carbon has a bonding capacity of 4 so each Group Highest Lower
formyl-
C atom must always make 4 bonds within a Precedence Precedence
[4]
If a compound is both an alkene and an
compound RC(=O)OH - oic acid 2
carboxy-
alkyne, both -ene and -yne are used
(carbo​xylic
 General Nomenc​lature acid)
 Haloal​kyl​s/Other Functional Groups
Usual follows order prefix + root + suffix RC(=O)OR' [branch]1- yl alkoxy​car​‐
Functional Group Prefix
Prefix Indicates name/m​ult​iplying prefix​‐ (ester) [root]1- oate bonyl-
1
R-O-R' (ether) [branch]-oxy-
es/​pos​ition of branches RC(=O)​ON(​‐ - amide carbamoyl-
R')​R" R-C-R (cyclo​alkyls) cyclo-
Root Indicates number of carbons in the
parent chain (amide) R-F fluoro-

Suffix Indicates the parent chain's RC≡N - nitrile cyano- R-Br bromo-
functional group (nitrile) R-Cl chloro-
RC=O - al 3 oxo- 3 R-I iodo-
 Root Name/B​ranch Prefixes (aldehyde)
R-NO2 nitro-
Number of C atoms Root Multip​lying RC(=O)R' - one oxo- 2
1,2-[b​ran​ch(es)] ortho-[bran​ch(es)]
/ branches prefix prefix (ketone)
2
1,3-[b​ran​ch(es)] meta-[bran​ch(es)]
1 meth- mono- R(OH)R' - ol hydroxy-
(alcohol) 1,4-[b​ran​ch(es)] 2 para-[bran​ch(es)]
2 eth- di -
[1]
R(N(R'​)R")​‐ - amine amino- Ethers take precedence in prefixes over
3 prop- tri-
R'" (amine) all other prefixes, except the branches
4 but- tetra-
attached to the ether group
RC=CR' - ene 4 Always
5 pent- penta- [2]
Applies only to benzene ring branches
(alkene) used as a
6 hex- hexa-
suffix
7 hep- hepta- 4
RC≡CR' - yne Always
8 oct - octa- (alkyne) used as a
suffix

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 Gr. 12 Organic Chemistry Cheat Sheet
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 Special Alkyl Branches  Alkynes  Alcohols

Propyl Butyl Contain at least one triple bond between C Any compound that contains a hydroxyl (R(-
n-propyl (normal) n-butyl (normal) atoms OH​)-R') group

isopropyl (y-shape) isobutyl (y-shape) General CnH2n-2 (n = whole number) General CnH2n-1OH (n = whole
chemical chemical number)
sec-butyl (2nd C)
formula formula
tert-butyl (t-shape)
Odour Almost odourless Odour Slightly pungent

 Alkanes Polarity Non-polar (only C-H bonds) Polarity Polar (between O-H bonds);
Solubility Slightly soluble longer C chains decrease in
Contain only single bonds between C atoms
in water polarity
General CnH2n+2 (n = whole number)
Boilin​g/m​‐ Depends on length of parent C Solubility Very soluble; longer C chains
chemical
elting chain (more C =  BP, less C in water decrease solubility
formula
point =  BP) Boilin​g/m​‐ Depends on length of parent C
Odour Odourless
elting chain (more C =  BP, less C
Polarity Non-polar (only C-H bonds)  Cycloalkyl point =  BP)
Solubility Slightly soluble Alkane​/al​ken​e/a​lkyne where the C atoms
in water  Aldehy​des​/Ke​tones
are joined in a ring shape
Boilin​g/m​‐ Depends on length of parent C General C2H2n (cycloalkane) Any compound that contains a carbonyl (R-
elting chain (more C =  BP, less C chemical C(=​O)-R') group
C2H2n-2 (cycloalkene)
point =  BP) formula Aldehydes have the carbonyl group at the
C2H2n-4 (cycloalkyne)
(n = whole number) first and/or last C atom of the molecule
 Alkenes
Odour Odourless/almost odourless Ketones have the carbonyl group in the
Contain at least one double bond between middle C atom(s) of the molecule
Polarity Non-polar (only C-H bonds)
C atoms
General CnH2nO (n = whole number)
Solubility Slightly soluble
General CnH2n (n = whole number) chemical
in water
chemical formula
formula Boilin​g/m​‐ Depends on length of parent C
Odour Pungent (aldehyde)
elting chain (more C =  BP, less C
Odour Almost odourless Sweet (ketone)
point =  BP)
Polarity Non-polar (only C-H bonds) Polarity Polar (between C=O bonds);
Solubility Slightly soluble longer C chains decrease
in water polarity

Boilin​g/m​‐ Depends on length of parent C Solubility Very soluble; longer C chains

elting chain (more C =  BP, less C in water decrease solubility
point =  BP)

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 Gr. 12 Organic Chemistry Cheat Sheet
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 Aldehy​des​/Ke​tones (cont)  Ethers (cont)  Interm​ole​cular Forces (IMFs)

Boilin​‐ Very high, increases with length of Polarity Polar (between C-O bonds); Forces that occur between molecules
g/m​‐ parent C chain (more C =  BP, longer C chains decrease Influence the physical properties of a
elting less C =  BP) polarity substance
point Solubility Very soluble; longer C chains Weaker than intramolecular forces (forces
in water decrease solubility within molecules)
 Carboxylic Acids/​Esters
Boilin​‐ Depends on length of parent C 3 main types:
Any compound that contains a carboxyl (R- g/m​elting chain (more C =  BP, less C
London Very weak forces that exist in
C(=​O)-​O-R') group point =  BP)
Dispersion all atoms/​mol​ecules caused
Carboxylic acids have the carboxyl group at
Forces by temporary charges due to
the first and/or last C atom of the molecule  Amines​/Amides
(LDF) e¯ shifts; become stronger
Esters have the carboxyl group in the Any compound that contains a N atom in a with more e¯
middle C atom(s) of the molecule carboxyl or carbonyl group
Dipole- Attraction between opposite
General CnH2nCOOH (n = whole Amines have N atoms in a carbonyl Dipole charges of polar molecules;
chemical number) group(s) (R-C(-​N(-​R')​-R")​-R'​") main reason for difference in
formula Amides have N atoms in a carboxyl meltin​g/b​oiling points
Odour Unpleasant (carbo​xylic acid) group(s) (R-C(=​O)-​N(-​R')​-R") Hydrogen Strong dipole​-dipole forces
Pleasant (ester) General CnH2n-1NO (n = whole bonding with H atoms covalently
Polarity Polar (between C=O bonds); chemical number) bonded with an N, O or F
longer C chains decrease formula atom
polarity Polarity Polar (between C=O, C-O and Strength of forces: (weakest) LDF 
Solubility Very soluble; longer C chains C-N bonds); longer C chains Dipole​-dipole  H-bonding (stron​gest)
in water decrease solubility decrease polarity
 Combustion Reactions
Boilin​‐ Very high, increases with length Solubility Very soluble; longer C chains
g/m​elting of parent C chain (more C =  in water decrease solubility All hydroc​arbons burn with oxygen gas
point BP, less C =  BP) State @ Depends on length of parent C (alkan​es/​alk​ene​s/a​lky​nes​/al​cohols)
SATP chain (more C = more solid, Combustion of CxHy + O2  CO2
 Ethers less C = more gas) hydroc​arbon + H2O
Any compound that contains an alkoxy (R- Combustion of CxHyOH + O2 
O-R') group alcohol CO2 + H2O
General chemical CnH2n+2O (n = whole
formula number)
Odour Slightly pungent

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 Gr. 12 Organic Chemistry Cheat Sheet
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 Elimin​ation Reactions  Addition Reactions (cont) Esterification/Hydrolysis of Esters

Take away 2 atoms to form double bond or The H atom of water/​hyd​rogen gas/hy​‐ Esteri​fic​ation
H2O drogen halide will always bond with the C Conden​sation reaction (forms H2O)
Also called conden​sat​ion​/de​hyd​ration atom that already had more H atoms
Catalyzed by concen​trated H2SO4 and
reactions bonded to it in an addition reaction
high heat
Elimin​‐ CxHyXz + [strong base]  Esteri​fic​‐ CxHyCOOH + CxHyOH 
Redox Reactions
ation of CxHy-1 + [halogen (X) salt] + ation [H2SO4] C2xH2yCO2 +
haloalkyl H2O Oxidation
H2O
C atoms will form more bonds to O atoms
Elimin​‐ CxHyOH  [conc acid]  Hydrolysis of Esters
ation of CxHy-1 + H2O Occurs when an organic compound reacts
Reverse reaction to esteri​fic​ation
alcohol with an oxidizing agent (usually
KMnO4/K2Cr2O7) Hydro = water, lysis = break

 Substi​tution Reactions Oxidation of CxHyOH [O]  Hydrolysis C2xH2yCO2 + H2O 

primary alcohol CxHy-1O (aldehyde ) of ester [H2SO4] CxHyCOOH +
Replace one atom with another
CxHyOH
Substi​tution CxHy + X2 [heat/​pre​‐ Oxidation of CxHyOH [O] 
reaction ssure] CxHy-1X + HX secondary CxHy-1O (ketone) Remember: Ester is a party girl; she drank
alcohol some alcohol and did some acid
Benzene rings
Oxidation of CxHyOH [O]  NO
Benzene does not have true double bonds,
tertiary alcohol  Synthe​sis​/Hy​dro​lysis of Amides
RXN
so only substi​tution reactions can be
Oxidation of CxHyO + H2O [O]  Synthesis of Amides
performed
aldehyde CxHy-1OH + H2 Conden​sation reaction (forms H2O)
Benzene C6H6 + X2  C6H5X +
substi​tution HX (carboxylic acid) Synthesis CxHyCOOH (carbo​xylic acid)
Reduction of amide + CxHyNH2 (amine) 
Benzene C6H5X + X2  C6H4X2
halide substi​‐ + HX C atoms will form fewer bonds to O atoms CxHyONH2 (amide) + H2O
tution Occurs when an organic compound reacts Hydrolysis of Amides
Halogen in benzene halide reactions forms with an reducing agent (usually H2/LiAlH4) Reverse reaction to synthesis
product meta position only (1,3-[​X]b​enzene) Hydrog​enation CxHyO + H2 [H] Hydrolysis CxHyONH2 (amide) + H2O
(reduction of CxHy+1OH (primary of amide  CxHyCOOH (carbo​xylic
 Addition Reactions aldehyde) alcohol) acid) + CxHyNH2 (amine)
Add atoms across double​/triple bond Hydrog​enation CxHyO + H2 [H]
Alkene​s/a​lkynes are nucleo​philes (they like (reduction of CxHy+1OH (secondary  Synthesis of Amines
to give up e_ ) ketone) alcohol) Amines can be made from haloalkyls using
Hydroh​alo​gen​‐ CxHy + HX  ammonia as a starting reactant
ation CxHy+1X Synthesis of CxHxX + NH3 
Haloge​nation CxHy + X2  primary amines CxHyNH2 + HX
CxHyX2 Synthesis of CxHxX + CxHyNH2
Hydrog​enation CxHy + H2  secondary  C2xH2yNH + HX
CxHy+2 amines

Hydration CxHy + H2O  Synthesis of CxHxX + C2xH2yNH

CxHy+1OH tertiary amines  C3xH3yN + HX

Markov​nikov's Rule: "the rich get richer​"

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 Gr. 12 Organic Chemistry Cheat Sheet
by NescafeAbusive32 (nescafeabusive32) via cheatography.com/53385/cs/14402/

 Polymers

Large molecules that are composed of

many repeated subunits called monomers
Created through polyme​riz​ation
Examples include plastics , DNA, and
proteins
Unique physical properties - checmi​cally
unreactive , flexible/mouldable /stretc​hable
Polyme​riz​‐ CxHy + CxHy+ CxHy+ ...
ation (addition  [CxHy]n
- chain
reaction of
alkene)
Polyme​riz​‐ HOCxHyOH +
ation (conde​‐ HOOCCxHyCOOH + ...
nsation with [O2CCxHyO2CxHyO2]n
alcohol -
polyester)
Polyme​riz​‐ H2NCxHyNH2 +
ation (conde​‐ HOOCCxHyCOOH + ...
nsation with [NOCCxHyO2CxHyON]n
alcohol -
polyamide)

Polyme​riz​ation (conde​nsa​tion) 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)

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