Organic Chemistry 💀

Notes: oxygen is king in naming order, numbers are separated by commas, letters and numbers are separated by dashes.

Main/parent chain

the longest continuous chain of carbon atoms in a compound

Structural isomers

molecules with identical empirical/molecular formulas, but with a different arrangement of atoms

Alkane

hydrocarbon compounds consisting of all single C-C bonds

general formula: C_nH_2n+2

Substituent

an atom or group of atoms that replaces a hydrogen atom/atoms on a carbon chain

Alkyl group

a substituent that consists of only carbon and hydrogen (e.g. a methyl group)

Alkene

hydrocarbon compounds containing one or more double C-C bonds

general formula: C_nH_2n

Alkynes

hydrocarbon compounds containing one or more triple C-C bonds

general formula: C_nH_2n-2

Functional groups

substituents which change the chemical properties of organic compounds

Halogenoalkane (halide)

carbon chain with F, Cl, Br, or I attached.

R-X

Ex: chloromethane

Alcohol (hydroxyl)

carbon chain with OH attached.

R-OH

Ex: propanol

Aldehyde (carbonyl)

carbon chain with C bonded to O and H at the end.

RCHO

Ex: ethanal

Ketone

carbon chain with C bonded to O somewhere in the middle.

R-COR’

Ex: Pentanone

Carboxylic acids (carboxyl)

carbon chain with C bonded to O and OH at the end.

R-COOH

Eg. ethanoic acid

Homologous series

different molecules that are members of the same chemical family (e.g. alkanes…) that differ from each other only by the number of CH₂ groups.

Trends - as chain length increases so does boiling point

Amine (amino)

carbon chain with NH₂ at the end or NH in the middle (for both options N has a lone pair)

R-NH₂ or R-N-R’

Ex. methylamine (H₃CNH₂)

Amide (amido)

carbon chain with C bonded to O and NH in the middle.

R-CO-N-R’

Arene (phenyl)

carbon chain bonded to ring of 6 Cs and 5 Hs

R-C₆H₅

Ester (ester)

carbon chain with C bonded to O bonded to O which is bonded to the rest of the chain.

R-COO-R’

Ether (alkoxy)

carbon chain with O in the middle (O has two lone pairs)

R-O-R

Nucleophile

a chemical species that is attracted to positive charges, can donate a pair of electrons

Ex. ligands, polar molecules, anions

Electrophile

a chemical species that is attracted to negative charges

Ex. cations

Free radical

highly reactive species due to the presence of an unpaired valence electrons. Unpaired electrons are shown as a dot

Ex. Cl•

Homolytic fission

the breaking of a covalent bond where each of the bonding species take one of the bonding electrons each

ex. Cl₂ → Cl• + Cl•

Heterolytic fission

the breaking of a covalent bond where one of the bonding species takes both of the bonding electrons

ex. Cl₂ → Cl^- + Cl⁺

Substitution

one species replaces another in an organic molecule

Addition

two or more molecules combine

Oxidation

characterized by a loss of electrons OR the gain of oxygen and/or the loss of hydrogen

Reduction

characterized by a gain of electrons OR the loss of oxygen and/or the gain of hydrogen

Combustion equations

Complete: fuel + O₂ → CO₂ + H₂O

Incomplete: fuel + O₂ → CO + C + H₂O

Free radical nucleophilic substitution (steps)

Initiation: UV radiation supplies the energy needed to initiate homolytic bond fission in the halogen, creating free radicals

Cl₂ → 2Cl•

Propagation: the free radicals are strong nucleophiles and will react with the alkane to produce and alkyl radical and a hydrogen halide

CH₄ + Cl• → CH₃• + HCl

CH₃• + Cl₂ → CH₃Cl + Cl•

Termination: free radicals produced will react with one another

Cl• + Cl• → Cl₂ OR CH₃• + Cl• → CH₃Cl

Electrophilic addition

occurs in alkenes and alkynes because the double bond breaks so each carbon can bond to one additional substituent.

Nucleophilic substitution

the nucleophile replaces the halogen, creating a new compound and a halide ion

Ex. C₂H₅Br+ OH^1- → C₂H₅OH + Br(dot)

Addition polymerization 

the double bond breaks & the C originally with the double bond now bonds to 2 new things

Condensation polymerization

the reacting molecules and product molecule have functional groups on the ends. Smaller molecules (often H₂O) are produced.

Diols - molecules with hydroxyl groups on each end (OH)

Dioc acids - molecules with carboxyl groups on each end (COOH)

Diamines - molecules with amino groups on each end (NH₂)

Primary carbon

when the carbon bonded to the functional group is also attached to 1 carbon

Secondary carbon

when the carbon bonded to the functional group is also attached to 2 carbons

Tertiary carbon

when the carbon bonded to the functional group is also attached to 3 carbons

Oxidation of primary alcohols

occurs in two oxidation steps: the first step produces an aldehyde through distillation, if the second step is allowed to occur, a carboxylic acid is produced through reflux.

C_xH_y + [O] → C_xH_y with CHO or COOH

Oxidation of secondary alcohols

occurs in one oxidation step which produces a ketone.

Oxidation of tertiary alcohols

cannot be oxidized

Reduction of organic compounds

Carboxylic acids → reduced to aldehydes using lithium aluminium hydride (Li[AlH₄])

Aldehydes → reduced to primary alcohols using sodium borohydride (NaBH₄)

Ketones → reduced to secondary alcohols using sodium borohydride (NaBH₄)

Saturation

When each carbon atom in an organic compound is bonded to the maximum number of hydrogen atoms (4)

Formula for IHD

(0.5)(2C + 2 - H - X + N), where X is a bonded halogen