Gr. 12 Organic Chemistry Cheat Sheet
by NescafeAbusive32 (nescafeabusive32) via cheatography.com/53385/cs/14402/
 Introduction
The term organic generally means
"something made from the earth" or "not
chemically synthesized."
Organic chemistry refers to the study of
compounds that contain carbon atoms as
the principal element.
The simplest organic compounds are
hyd

roc

arb

ons made from C and H atoms
Despite the term organic generally meaning
"natural," organic compounds can in fact be
chemically synthesized (first synthesized
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 Nomenclature
Usual follows order prefix + root + suffix
Prefix Indicates name/

mul

tip

lying
prefix

es/

pos

ition of branches
Root Indicates number of carbons in the
parent chain
Suffix Indicates the parent chain's funct

ional
group
 Root Name/Branch Prefixes
Number of C atoms /
branches
Root
prefix
Multiplying
prefix
1meth-mono-
2eth-di-
3prop-tri-
4but-tetra-
5pent-penta-
6hex-hexa-
7hep-hepta-
8oct-octa-
 
 Root Name/Branch Prefixes (cont)
9non-nona-
10 dec-deca-
Special nomenclature prefixes:  See
Impor

tance of Functional Groups,
Haloa

lky

l/Other Functional Groups, and Special
Alkyl Branches
All prefixes are listed in alpha order when
writing the name of an organic compound,
except for cyc

lo- and iso

-.
 Importance of Functional Groups
Functional
Group
Suffix if
Highest
Precedence
Prefix if
Lower
Precedence
RC(=O)OH
(carboxylic acid)
-oic acid carboxy-
RC(=O)OR'
(ester)
[branch] -y
l
[root] -oate
alkox

yca

rbo

nyl-
RC(=O)ON(R')R"
(amide)
-amide carba

moyl
-
RC≡N (nitrile) -nitrile cyano-
RC=O
(aldehyde)
-al oxo-
RC(=O)R'
(ketone)
-one oxo-
R(OH)R'
(alcohol)
-ol hydroxy-
R(N(R')R")R'"
(amine)
-amine amino-
RC=CR' (alkene) -ene  Always
used as a
suffix
RC≡CR' (alkyne) -yne  Alw ays
used as a
suffix
 
 Importance of Functional Groups (cont)
RCCR'
(alkane)
-ane Always used as a
suffix
R(X)R' Always
used as a
prefix
See
Haloa

lky

ls/

Other
Functional Groups
[branch] and [root] refer to the length of the
carbon group's prefix (meth-, eth-, prop-, etc.)
If the carbon in the RCOOH group is not the
parent chain, the highest precedence suffix is
-carb

oxylic acid
If the carbon in the RCO group is not the
parent chain, the highest precedence suffix is
-carb

ald

ehyde , and the alternate prefix is
formyl-
If a compound is both an alkene and an
alkyne, both -ene and -yne are used
 Haloalkyls/Other Functional Groups
Functional Group Prefix
R-O-R' (ether) [branch]-oxy-
R-C-R (cycloalkyls) cyclo-
R-F fluoro-
R-Br bromo-
R-Cl chloro-
R-I iodo-
R-NO2nitro-
1,2-[branch(es)] ortho

-[branch(es)]
1,3-[branch(es)] meta-[branch(es)]
1,4-[branch(es)] para-[branch(es)]
Ethers take precedence in prefixes over all
other prefixes, except the branches attached to
the ether group
Applies only to benzene ring branches
By NescafeAbusive32
(nescafeabusive32)
cheatography.com/nescafeabusive32/
 
Published 23rd January, 2018.
Last updated 29th December, 2018.
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by NescafeAbusive32 (nescafeabusive32) via cheatography.com/53385/cs/14402/

 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 -  Root Name/Branch Prefixes (cont) 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 carboxy - RC(=O)OR' (ester) [branch] - y l [root] - oate alkoxycarbo nyl - RC(=O)ON(R')R" (amide)
amide carbamoyl

RC≡N (nitrile) - nitrile cyano - RC=O (aldehyde)

al oxo - RC(=O)R' (ketone)
one oxo - R(OH)R' (alcohol)
ol hydroxy - R(N(R')R")R'" (amine)
amine amino - RC=CR' (alkene) - ene Always used as a suffix RC≡CR' (alkyne) - yne Always used as a suffix  Importance of Functional Groups (cont) RCCR' (alkane)
ane Always used as a suffix R(X)R' Always used as a prefix See Haloalkyls/Other Functional Groups [branch] and [root] refer to the length of the carbon group's prefix ( meth -, eth -, prop -, etc.) If the carbon in the RCOOH group is not the parent chain, the highest precedence suffix is
carboxylic acid If the carbon in the RCO group is not the parent chain, the highest precedence suffix is
carbaldehyde , and the alternate prefix is formyl - 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) [branch]- oxy - R-C-R (cycloalkyls) cyclo - R-F fluoro - R-Br bromo - R-Cl chloro - R-I iodo - R-NO 2 nitro - 1,2-[branch(es)] ortho -[branch(es)] 1,3-[branch(es)] meta -[branch(es)] 1,4-[branch(es)] para -[branch(es)] Ethers take precedence in prefixes over all other prefixes, except the branches attached to the ether group Applies only to benzene ring branches By NescafeAbusive (nescafeabusive32) Published 23rd January, 2018. Last updated 29th December, 2018. Page 1 of 5. Sponsored by ApolloPad.com Everyone has a novel in them. Finish Yours! https://apollopad.com 2 1 1 3 3 4 4 [1] [2] [3] [4] 1 2 2 2 [1] [2]

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 Special Alkyl Branches Propyl Butyl n-propyl (normal) n-butyl (normal) isopropyl (y-shape) isobutyl (y-shape) sec-butyl (2 C) tert-butyl (t-shape)  Alkanes Contain only single bonds between C atoms General chemical formula CnH2n+2 (n = whole number) Odour Odourless Polarity Non-polar (only C-H bonds) Solubility in water Slightly soluble Boiling/me lting 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 CnH2n (n = whole number) Odour Almost odourless Polarity Non-polar (only C-H bonds) Solubility in water Slightly soluble Boiling/me lting 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 CnH2n-2 (n = whole number) Odour Almost odourless Polarity Non-polar (only C-H bonds) Solubility in water Slightly soluble Boiling/me lting 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 H2n (cycloalkane) C 2 H2n-2 (cycloalkene) C 2 H2n-4 (cycloalkyne) (n = whole number) Odour Odourless/almost odourless Polarity Non-polar (only C-H bonds) Solubility in water Slightly soluble Boiling/me lting 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 CnH2n-1OH (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/me lting 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 CnH2nO (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 By NescafeAbusive (nescafeabusive32) Published 23rd January, 2018. Last updated 29th December, 2018. Page 2 of 5. Sponsored by ApolloPad.com Everyone has a novel in them. Finish Yours! https://apollopad.com nd

by NescafeAbusive32 (nescafeabusive32) via cheatography.com/53385/cs/14402/

 Elimination Reactions Take away 2 atoms to form double bond or H 2 O Also called condensation/dehydration reactions Elimination of haloalkyl CxHyXz + [strong base]  CxHy-1 + [halogen (X) salt] + H 2 O Elimination of alcohol CxHyOH  [conc acid]  CxHy-1 + H 2 O  Substitution Reactions Replace one atom with another Substitution reaction CxHy + X 2  [heat/pressure] CxHy- 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 ) Hydrohalogenatio n CxHy + HX  CxHy+1X Halogenation CxHy + X 2  CxHyX 2 Hydrogenation CxHy + H 2  CxHy+ Hydration CxHy + H 2 O  CxHy+1OH Markovnikov's Rule: "the rich get richer"  Addition Reactions (cont) 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 CxHyOH  [O]  CxHy-1O ( aldehyde ) Oxidation of secondary alcohol CxHyOH  [O]  CxHy-1O ( ketone ) Oxidation of tertiary alcohol CxHyOH  [O]  NO RXN Oxidation of aldehyde CxHyO + H 2 O  [O]  CxHy-1OH + 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) CxHyO + H 2  [H] CxHy+1OH ( primary alcohol ) Hydrogenation (reduction of ketone) CxHyO + H 2  [H] CxHy+1OH ( secondary alcohol )  Esterification/Hydrolysis of Esters Esterification Condensation reaction (forms H 2 O) Catalyzed by concentrated H 2 SO 4 and high heat Esterifica tion CxHyCOOH + CxHyOH  [H 2 SO 4 ] C2xH2yCO 2 + H 2 O Hydrolysis of Esters Reverse reaction to esterification Hydro = water, lysis = break Hydrolysi s of ester C2xH2yCO 2 + H 2 O  [H 2 SO 4 ] CxHyCOOH + CxHyOH 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) Synthe sis of amide CxHyCOOH (carboxylic acid) + CxHyNH 2 ( amine )  CxHyONH 2 ( amide ) + H 2 O Hydrolysis of Amides Reverse reaction to synthesis Hydrol ysis of amide CxHyONH 2 ( amide ) + H 2 O  CxHyCOOH (carboxylic acid) + CxHyNH 2 ( amine )  Synthesis of Amines Amines can be made from haloalkyls using ammonia as a starting reactant Synthesis of primary amines CxHxX + NH 3  CxHyNH 2 + HX Synthesis of secondary amines CxHxX + CxHyNH 2  C2xH2yNH + HX Synthesis of tertiary amines CxHxX + C2xH2yNH  C3xH3yN + HX By NescafeAbusive (nescafeabusive32) Published 23rd January, 2018. Last updated 29th December, 2018. Page 4 of 5. Sponsored by ApolloPad.com Everyone has a novel in them. Finish Yours! https://apollopad.com _

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 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) CxHy + CxHy+ CxHy+ ...  [CxHy]n Polymerization (condensation with alcohol - polyester) HOCxHyOH + HOOCCxHyCOOH + ...  [O 2 CCxHyO 2 CxHyO 2 ]n Polymerization (condensation with alcohol - polyamide) H 2 NCxHyNH 2 + HOOCCxHyCOOH + ...  [NOCCxHyO 2 CxHyON]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 ) By NescafeAbusive (nescafeabusive32) Published 23rd January, 2018. Last updated 29th December, 2018. Page 5 of 5. Sponsored by ApolloPad.com Everyone has a novel in them. Finish Yours! https://apollopad.com

Organic Chemistry Cheat Sheet, Cheat Sheet of Organic Chemistry

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by NescafeAbusive32 (nescafeabusive32) via cheatography.com/53385/cs/14402/

by NescafeAbusive32 (nescafeabusive32) via cheatography.com/53385/cs/14402/

C 6 H 6 + X 2  C 6 H 5 X +

HX

C 6 H 5 X + X 2  C 6 H 4 X 2

+ HX

by NescafeAbusive32 (nescafeabusive32) via cheatography.com/53385/cs/14402/