Organic Chemistry The study of carbon and carbon-containing compounds

Properties of Organic Compounds MUST contain CARBON and hydrogen Generally poor (non) conductors of electricity and heat Low Melting Point / Low Boiling Point (More C atoms means higher BP/MP) Hydrocarbons are INSOLUBLE in water Generally soluble in nonpolar solvents

The Carbon Atom Forms 4 covalent bonds Has 4 valence electrons, needs 4 more Four electron pairs occupy the corners of a tetrahedron (shapes) Carbon can form single or multiple covalent bonds with other elements and other carbon atoms *Reminder: each covalent bond represents a pair of (2) electrons

Homologous Series of Hydrocarbons List of hydrocarbons in which each member has ONE more C than the last Each has 2 more H atoms Alkanes: saturated (all single bonds) Alkenes: unsaturated (double bond) Alkynes: unsaturated (triple bond)

Naming Simple Organic Compounds Count the number of carbon atoms in the longest continuous chain Refer to Table P for prefix Add the appropriate ending based on the bonding In front of the name, number the position of a multiple bond with the SMALLEST number possible The letter n means “normal” (straight chain)

Naming Branched Organic Compounds Name the longest continuous chain based on the C atoms (must include any multiple bonds) Use Table P for prefixes of alkyl groups (branches) Number the position of the alkyl group with the SMALLEST number possible (in front) There is a number for each alkyl group (the number of numbers is the same as the number of branches) Use prefixes (di, tri, tetra) if needed

Structural Isomers Two compounds that have the SAME molecular formula, but DIFFERENT structures Have DIFFERENT chemical and physical properties Have the SAME empirical formula, molecular mass, and percent composition Larger compounds have more structural isomers Ask me about cis and trans

Different Kinds of Formulae Molecular FormulaC 2 H 6 Empirical FormulaCH 3 Structural Formula(See Board) Condensed Structural Formula

Organic Functional Groups

Something other than carbon and hydrogen in an organic compound ** Compounds with the same functional group have similar chemical properties Table R is extremely helpful! Use it to understand the naming system

Halides (Halocarbons) Like a hydrocarbon where one or more group 17 atoms have replaced hydrogen(s) Start by naming the longest continuous chain (P and Q) Add the correct prefix May need di, tri, tetra…

Alcohols Like a hydrocarbon where one or more hydrogen atoms are replaced with OH groups Start by naming the longest continuous chain (P and Q) **Ending: drop the –e and add -ol May need number to indicate where the OH group is located Primary, Secondary, Tertiary Mono, Di, Tri Hydroxy

Ethers Oxygen in the middle of a carbon chain (not at one of the ends) Name pieces on either side of O as alkyl groups (Use Table P) End with the word ether

Aldehyde Double bonded oxygen and a hydrogen off of an end of a carbon chain Carbon chain may be single bonded despite the double bond O **Ending: drop the –e and add –al No need for a number

Ketone Double-bonded oxygen in the middle of a carbon chain Name based on C in the chain (Table P) **Ending: drop the –e and add –one Number the position of the double bonded O

Organic Acid - COOH group at the end of a chain (H is donated) Name based on number of C atoms in chain **Ending: drop the –e and add –oic acid No need for a number

Esters -COO- group in the middle of a chain (not at an end) -COO- group in the middle of a chain (not at an end) Name based on two pieces Name based on two pieces “Backbone” piece contains both O atoms; name based on number of C atoms and change ending to -oate “Backbone” piece contains both O atoms; name based on number of C atoms and change ending to -oate Other piece name as an alkyl group (with the –yl ending) Other piece name as an alkyl group (with the –yl ending)

Amine Two systems of naming Two systems of naming 1 st : -NH 2 group added to a carbon chain 1 st : -NH 2 group added to a carbon chain Name based on number of C atoms in chain Name based on number of C atoms in chain Ending: drop the –e and add –amine Ending: drop the –e and add –amine Add number for which C atom contains the amine Add number for which C atom contains the amine 2 nd : If more than one carbon chain comes off of the N 2 nd : If more than one carbon chain comes off of the N Name the branches as alkyl groups and add the word amine Name the branches as alkyl groups and add the word amine

Amide When -CONH 2 group at the end of a chain: When -CONH 2 group at the end of a chain: Name the carbon chain based on the C atoms Name the carbon chain based on the C atoms Ending: drop the –e and add –amide Ending: drop the –e and add –amide

Amino Acids One side has an amine group One side has an amine group The other side has an organic acid group The other side has an organic acid group “R” group could be one of many different functional groups “R” group could be one of many different functional groups “R” group differentiates the amino acid “R” group differentiates the amino acid When –CONH- in the middle of a chain, result of an amide bondWhen –CONH- in the middle of a chain, result of an amide bond Proteins are polymers of amino acids that link together with amide bondsProteins are polymers of amino acids that link together with amide bonds

Organic Chemistry Reactions Combustion The complete combustion of a hydrocarbon produces carbon dioxide and water The complete combustion of a hydrocarbon produces carbon dioxide and water C 3 H O 2  3 CO H 2 O C 3 H O 2  3 CO H 2 O The incomplete combustion can produce carbon monoxide and water The incomplete combustion can produce carbon monoxide and water

Halogen Substitution 2 reactants and 2 products 2 reactants and 2 products The hydrocarbon reactant is saturated The hydrocarbon reactant is saturated C 3 H 8 + Cl 2  C 3 H 7 Cl + HCl C 3 H 8 + Cl 2  C 3 H 7 Cl + HCl A halogen atom replaces a hydrogen atom in the compound A halogen atom replaces a hydrogen atom in the compound

Halogen Addition 2 reactants and 1 product 2 reactants and 1 product The hydrocarbon reactant is unsaturated The hydrocarbon reactant is unsaturated C 2 H 4 + Br 2  C 2 H 4 Br 2 C 2 H 4 + Br 2  C 2 H 4 Br 2 Both atoms of the halogen molecule are added to the compound Both atoms of the halogen molecule are added to the compound The multiple bond reduces The multiple bond reduces

Fermentation A sugar breaks down into an alcohol (ethanol) and CO 2 A sugar breaks down into an alcohol (ethanol) and CO 2 C 6 H 12 O 6  2 C 2 H 5 OH + 2 CO 2 C 6 H 12 O 6  2 C 2 H 5 OH + 2 CO 2 Happens in the presence of yeast Happens in the presence of yeast

Esterification An organic acid and an alcohol combine to form an ester and H 2 O An organic acid and an alcohol combine to form an ester and H 2 O Think of Naming Esters Think of Naming Esters Dehydration Synthesis Dehydration Synthesis ** Formation of a triglyceride from glycerol and 3 fatty acids ** Formation of a triglyceride from glycerol and 3 fatty acids

Saponification Making soap from fat (triglyceride) and a base Making soap from fat (triglyceride) and a base Glycerol is another product Glycerol is another product The OH - breaks apart the ester bonds The OH - breaks apart the ester bonds * Only organic reaction involving a base * Only organic reaction involving a base * Recognize the size of the fatty acid chains * Recognize the size of the fatty acid chains

Polymerization: Monomers linking together to form a long continuous chain Addition Polymerization Addition Polymerization “2 reactants and 1 product” “2 reactants and 1 product” Lone Product: polymer chain one unit longer Lone Product: polymer chain one unit longer The monomer must be unsaturated The monomer must be unsaturated

Condensation Polymerization “2 reactants and 2 products” “2 reactants and 2 products” Many condensation polymerization reactants are dihydroxy alcohols Many condensation polymerization reactants are dihydroxy alcohols H and OH are removed H and OH are removed Products: the new polymer one unit longer and water Products: the new polymer one unit longer and water