Ms. Capasso’s Awesome Organic Chemistry Review Sheet!

Organic Chemistry is the study of carbon and its compounds. Carbon has four valence electrons and therefore can make four different

bonds Carbon can make infinitely complex chains and rings leading to a wide

variety of complex molecules which is important for sustaining life

Vocabulary Hydrocarbon – a compound that only has hydrogen and oxygen; example-

propane Aliphatic – a straight-line carbon chain Cyclocarbon – a carbon chain that is in a closed ring Aromatic carbon – a carbon ring that contains alternating single and double

bonds leading to a delocalized system of pi bonds Substituents (side-chains) – a group of atoms that branch off of the main

carbon chain IUPAC – the International Union of Pure and Applied Chemistry; refers to the

governing body which makes globally recognized naming convention for organic molecules

Functional Group - any group that replaces a hydrogen in a hydrocarbon chain leading to different physical and chemical properties for that group

Saturated Unsaturated Compounds which contain only

single bonds Alkanes

Compounds which contain double or triple bonds

Alkenes, alkynes Homologous Series:

Organic compounds may be grouped into “families” of compounds known as homologous series

The members of each homologous series contain certain common features and/or general formula

We learned about three homologous series: alkane, alkenes and alkynes

Family General Formula

Saturated or Unsaturated

Bonds Naming

Alkanes CnH2n+2 Saturated All single End in –aneAlkenes CnH2n+2 Unsaturated One double End in –eneAlkynes CnH2n-2 Unsaturated One triple End in -yne

If the third member of a family is C3H8 than the fifth member is C5H12

Physical Properties – Organic Compounds1. Mostly non-polar2. React slower than inorganic compounds3. Almost all covalent compounds4. Weak intermolecular forces* (London Dispersion)5. Low melting point and low boiling point6. Not soluble in water

*The exception being those compounds that contain hydrogen bonds

Within a homologous series, as the molecules get bigger, the intermolecular forces (London Dispersion) get stronger and melting point and boiling point get higher! Example: Decane has a much higher boiling point than methane!

Formulas for organic compounds:Empirical Shows the simplest whole number ratio of the atoms it

containsExample: CH2O

Molecular Shows the actual number of atoms of each molecule contained in the compoundExample: C6H12O6

Structural Shows how the atoms are bound together

Within structural formulas, there are three different types:Full Structural Shows exactly how the atoms are bonded together

Condensed Structural

Omits showing bonds and instead tries to unambiguously show the structure of the molecule with minimal information

Example: CH3CH2CH2CH2CH2CCCH2CH3 is 3-nonyne (alkyne)Stereochemical Attempts to show position of atoms and three dimensional

position in space; do not need for Regents

Nomenclature – IUPAC Naming

IUPAC naming conventions give all scientists a logical way to name organic compounds

Steps1. Identify the longest hydrocarbon chain and give it a prefix (i.e. meth, eth, pro,

etc.)2. Identify the functional groups and give them a name. This can be either some

sort of prefix (i.e. cloro, methyl, etc.) or a suffix change (i.e –ol for alcohols)3. Identify any side chains and give them a name (i.e. methyl, ethyl, etc.)4. Number your carbons left to right and right to left. Choose the numbering

that gives the functional groups, side chains and multiple bonds the lowest numbers possible. Choose only one way!

5. Give each of your functional groups, side chains and multiple bonds a number based on what carbon they are bound to

6. Complete your name by choosing the proper suffix based on the functional group or double/triple bonds

Isomers Isomers are compounds that have the same molecular formula but a different

structural formula Example: C5H12

Three Isomers

Functional Groups Functional groups can be found on Table R Naming conventions can be gathered by looking at Table R; derive their

name from the un-substituted carbon chain

Functional Group

What is it? How is it named? Why is it important?

Halide -Br -I -F -Cl attached to a hydrocarbon

“1-chloro”With a number and a name before the parent chain

Used in refrigerators and as propellantsOrganic solvents and pesticides

Alcohol -O-H (hydroxyl group) attached to carbon chain

Changing the -e in the ending to -ol

Cleaning, fuel and beverages

Ether -O- Common way – (Regents does not go into IUPAC_ - name both side chains and then say “ether”. No set rules on which one goes first!

Anesthesia

Aldehyde -C=O H

A carbon with one double bond to an O. Only bound to one other carbon

Change the final “e” to “al”

E.g. propanal

Smell good; vanilla and cinnamon

Ketone -C=O |

A carbon bound to two other carbons and also double bound to oxygen

Change the final “e” to “-one”

E.g. propanone

Great solvents!

Organic Acid

-COOH

Carbon double bound to an O and single bound to an O-H group

Change the ending to “oic acid”

Acids! Used in a lot of biochemical reactions keeping us alive

Ester -COOC-

Carbon double bound to an O and single bound to another C and an O

The compound that used to be the acid gets it ending changed to “-oate” and the other named before

Smells good – bananas, wintergreen, pineapple, etc.

Amine -N-

Nitrogen bound to carbon with single bonds

Change final “e” and add “-amine”

E.g. methamine

Important in Biology – B vitamins, hormones, etc.

Amide R-C-N-R’ || O

Also called a peptide linked. Only when terminal, change final “e” and add “-

Important for life! Also called a peptide bond because it holds proteins together

amide”

Alcohols: Can be classified as primary, secondary, or tertiary depending on what

carbon the hydroxyl (-OH) group is bound to Can also be classified for how

many hydroxyl groups there are in a molecule

Trihydroxyl Alcohol

Amino Acids Contain an organic acid group and an amine group Connect together using condensation or dehydration synthesis; resulting

bond is an amide Building block of proteins!

Primary – the carbon –OH is attached to only attached to one other carbonSecondary – the carbon –OH is attached to attached to two other C’sTertiary – carbon –OH attached to attached to 3 other C’s

Organic Reactions Combustion – Burning a hydrocarbon in oxygen until it makes CO2 plus H2O

Substitution - Saturated hydrocarbons have all their bonding sites filled with hydrogen. In substitution, one of the hydrogen atoms is replaced with something else (Example: One of the halogens (Group 17) replaces a hydrogen - Br, Cl, or OH)

Addition – When two atoms are adding across a double or triple bond

Fermentation – Alcohol formed by yeast breaking down sugar; yeast cells secrete an enzyme called zymase which breaks down the six-carbon chain of sugar into CO2 and two alcohol molecules

Esterification – Esters form from the reaction of an organic acid and alcohol by the removal of one water molecules

Saponification – The hydrolysis of fats by bases to make a soap and a salt; an ester reacts with an inorganic base like NaOH to make soap and a salt

Polymerization – Small molecules (monomers) are combined to make larger molecules of repeating units called polymers

o Condensation : Polymer forms by the removal of water

o Addition : Involves the opening up of double or triple bonds