IntroductionThe 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 NomenclatureUsual 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 PrefixesNumber 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 GroupsFunctional Group | Suffix if Highest Precedence
| Prefix if Lower Precedence | | -oic acid 2 | carboxy- | | [branch]1-yl [root]1-oate | alkoxycarbonyl- | | -amide | carbamoyl- | | -nitrile | cyano- | | -al 3 | oxo-3 | | -one | oxo- | | -ol | hydroxy- | | -amine | amino- | | -ene 4 | Always used as a suffix | | -yne 4 | Always used as a suffix | | -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 GroupsFunctional Group | Prefix | | [branch]-oxy- | | 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
| | AlkanesContain only single bonds between C atoms | General chemical formula | Cn H2n+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) |
AlkenesContain at least one double bond between C atoms | General chemical formula | Cn H2n (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) |
AlkynesContain at least one triple bond between C atoms | General chemical formula | Cn H2n-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) |
CycloalkylAlkane/alkene/alkyne where the C atoms are joined in a ring shape | General chemical formula | C2 H2n (cycloalkane) C2 H2n-2 (cycloalkene) C2 H2n-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) |
AlcoholsAny compound that contains a hydroxyl (R(-OH)-R') group | General chemical formula | Cn H2n-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/KetonesAny 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 | Cn H2n 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/EstersAny 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 | Cn H2n 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) |
EthersAny compound that contains an alkoxy (R-O-R') group | General chemical formula | Cn H2n+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/AmidesAny 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 | Cn H2n-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 ReactionsAll hydrocarbons burn with oxygen gas (alkanes/alkenes/alkynes/alcohols) | Combustion of hydrocarbon | Cx Hy + O2 CO2 + H2 O | Combustion of alcohol | Cx Hy OH + O2 CO2 + H2 O |
Elimination ReactionsTake away 2 atoms to form double bond or H2 O | Also called condensation/dehydration reactions | Elimination of haloalkyl | Cx Hy Xz + [strong base] Cx Hy-1 + [halogen (X) salt] + H2 O | Elimination of alcohol | Cx Hy OH [conc acid] Cx Hy-1 + H2 O |
Substitution ReactionsReplace one atom with another | Substitution reaction | Cx Hy + X2 [heat/pressure] Cx Hy-1 X + HX | Benzene rings | Benzene does not have true double bonds, so only substitution reactions can be performed | Benzene substitution | C6 H6 + X2 C6 H5 X + HX | Benzene halide substitution | C6 H5 X + X2 C6 H4 X2 + HX | Halogen in benzene halide reactions forms product meta position only (1,3-[X]benzene) |
Addition ReactionsAdd atoms across double/triple bond | Alkenes/alkynes are nucleophiles (they like to give up e_) | Hydrohalogenation | Cx Hy + HX Cx Hy+1 X | Halogenation | Cx Hy + X2 Cx Hy X2 | Hydrogenation | Cx Hy + H2 Cx Hy+2 | Hydration | Cx Hy + H2 O Cx Hy+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 ReactionsOxidation | C atoms will form more bonds to O atoms | Occurs when an organic compound reacts with an oxidizing agent (usually KMnO4 /K2 Cr2 O7 ) | Oxidation of primary alcohol | Cx Hy OH [O] Cx Hy-1 O (aldehyde) | Oxidation of secondary alcohol | Cx Hy OH [O] Cx Hy-1 O (ketone) | Oxidation of tertiary alcohol | Cx Hy OH [O] NO RXN | Oxidation of aldehyde | Cx Hy O + H2 O [O] Cx Hy-1 OH + H2 (carboxylic acid) | Reduction | C atoms will form fewer bonds to O atoms | Occurs when an organic compound reacts with an reducing agent (usually H2 /LiAlH4 ) | Hydrogenation (reduction of aldehyde) | Cx Hy O + H2 [H] Cx Hy+1 OH (primary alcohol) | Hydrogenation (reduction of ketone) | Cx Hy O + H2 [H] Cx Hy+1 OH (secondary alcohol) |
Esterification/Hydrolysis of EstersEsterification | Condensation reaction (forms H2 O) | Catalyzed by concentrated H2 SO4 and high heat | Esterification | Cx Hy COOH + Cx Hy OH [H2 SO4 ] C2x H2y CO2 + H2 O | Hydrolysis of Esters | Reverse reaction to esterification | Hydro = water, lysis = break | Hydrolysis of ester | C2x H2y CO2 + H2 O [H2 SO4 ] Cx Hy COOH + Cx Hy OH |
Remember: Ester is a party girl; she drank some alcohol and did some acid
Synthesis/Hydrolysis of AmidesSynthesis of Amides | Condensation reaction (forms H2 O) | Synthesis of amide | Cx Hy COOH (carboxylic acid) + Cx Hy NH2 (amine) Cx Hy ONH2 (amide) + H2 O | Hydrolysis of Amides | Reverse reaction to synthesis | Hydrolysis of amide | Cx Hy ONH2 (amide) + H2 O Cx Hy COOH (carboxylic acid) + Cx Hy NH2 (amine) |
Synthesis of AminesAmines can be made from haloalkyls using ammonia as a starting reactant | Synthesis of primary amines | Cx Hx X + NH3 Cx Hy NH2 + HX | Synthesis of secondary amines | Cx Hx X + Cx Hy NH2 C2x H2y NH + HX | Synthesis of tertiary amines | Cx Hx X + C2x H2y NH C3x H3y N + HX |
PolymersLarge 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) | Cx Hy + Cx Hy + Cx Hy + ... [Cx Hy ]n | Polymerization (condensation with alcohol - polyester) | HOCx Hy OH + HOOCCx Hy COOH + ... [O2 CCx Hy O2 Cx Hy O2 ]n | Polymerization (condensation with alcohol - polyamide) | H2 NCx Hy NH2 + HOOCCx Hy COOH + ... [NOCCx Hy O2 Cx Hy 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)
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