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 |
|
-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 Groups
Functional 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
|
|
Alkanes
Contain 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) |
Alkenes
Contain 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) |
Alkynes
Contain 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) |
Cycloalkyl
Alkane/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) |
Alcohols
Any 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/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 |
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/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 |
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) |
Ethers
Any 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/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 |
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 Reactions
All 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 Reactions
Take 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 Reactions
Replace 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 Reactions
Add 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 Reactions
Oxidation |
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 Esters
Esterification |
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 Amides
Synthesis 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 Amines
Amines 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 |
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) |
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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