Organic Chemistry Template from: PresenterMedia.comPresenterMedia.com

Organic Compounds Organic compounds are molecules that contain carbon. Carbon is the base of organic compounds for 3 reasons: 1. Carbon forms stronger covalent bonds than most other non-metals 2. Carbon forms more stable molecules than most other non-metals 3. Carbon can form up to 4 bonds at a time, which gives many possibilities for molecules.

Structure of Organic Compounds Besides carbon, the most common elements in organic compounds are: H, O, N, S, & halogens. Organic compounds are held together with covalent bonds. Organic compounds must meet the octet rule (S does not break the octet rule)

Hydrocarbons Hydrocarbons are the most simple organic compounds Hydrocarbons only contain C & H All other organic compounds are derivatives of hydrocarbons Petrochemicals contain hydrocarbons, including: propane, butane, and octane Saturated – a compound is termed “saturated” if it has the maximum hybridization (sp 3 ) at each carbon! Therefore: no double or triple bonds

Hydrocarbons C 2 H 6 Alkanes Single bonded carbons Strongest, most stable hydrocarbons C n H 2n+2 saturated C 2 H 4 Alkenes A double bonded carbon Weaker, less stable hydrocarbo ns C n H 2n unsaturated C 2 H 2 Alkynes A triple bonded carbon Weakest, least stable hydrocarbons C n H 2n-2 unsaturated C 6 H 6 Aromatics Ring of carbons with alternating double and single bonds C 6 H 12 cycloalkane ring C n H 2n unsaturated

Simple Organic Nomenclature Prefixes used with organic compounds 1. meth- 6. hex- 2. eth-7. hept- 3. prop- 8. oct- 4. but-9. non- 5. pent-10. dec- Name the following organic compounds a. CH 4 ___________________ b. C 3 H 8 ___________________ c. C 3 H 6 ___________________ d. C 4 H 10 ___________________ e. C 5 H 8 ___________________ f. C 3 H 4 ___________________ methane propane propene butane pentyne propyne Suffixes used with organic compounds -ane = C n H 2n+2 -ene = C n H 2n -yne = C n H 2n-2

Nomenclature Rules Procedure for naming carbon chains containing branches or substituents (non-straight chain) 1) Find the longest continuous carbon chain in the structure-this determines the root name 2) Any carbon not on this continuous chain is a substituent (appendage) 3) Number the main chain starting from the end closest to the first substituent 4) The substituents are still named according to the number of carbons (the suffix for a substituent is –yl instead of –ane) -CH 3 methyl -CH 2 CH 3 ethyl 5) Place all substituent names before the root name in alphabetical order 6) The substituent must be numbered to indicate the point of attachment to the main chain 7) Group multiple substituents of the same kind together and label di-, tri-, etc. 8) When alphabetizing, the prefixes di-, tri- are ignored 9) With a ring compound the number of carbons in the ring determines the root name with a cyclo- prefix 10) Halogens are named as substituents with an -o suffix e.g. fluoro-, chloro-, bromo- or iodo-

Isomers - Compounds with the same molecular formula but different structural arrangement therefore a different name. A. hexane B. 2-methylpentane C. 3-methylpentane D. 2, 2-dimethylbutane E. 2,3-dimethylbutane C 6 H 14

1-Butene 3-Heptyne Draw & Name the following C H H H HCCC H HH H C H H H HCCC H HH CCC HHH HH C4H8C4H8 C 7 H 12

C 3 H 6 or CH 3 CH=CH 2 C 4 H 8 or H 2 C=CHCH 2 CH 3 C H H H C H C H 1-propene H H H H H CC H C H C H 1-Butene H

Functional Groups Functional groups are any atom, group of atoms, or organization of bonds that determine the properties of a molecule. Functional groups are the most reactive part of a molecule Functional groups directly determine the properties of a molecule

Functional Groups a. Alcohols: -OH When carbon is single bounded to an –OH Ex. Propanol 3-pentanol Add –ol to name H H H H CC H HC H O H

b. Aldehydes: -C=OH - always on the end Example: c. Carboxylic Acids: COOH Most common organic acids belong to this group. Example: pentanal Add –al to name Propanoic Acid Add –oic Acid to name

d. Ketones: -C=O (also called a carbonyl group) Example: e. Esters are formed when a carboxylic acid reacts with an alcohol. This reaction is called esterification. –O-C=O Example: methyl butanoate Add –oate to name Smells like pineapple 4 -octanone Add –one to name

f. Halohydrocarbons: Halogen substituted for a hydrogen Example: F H Br F CC Cl F 2-bromo-2-chloro-1,1,1-trifluoroethane.

Polymers Polymers are long carbon chains made of repeating units Both natural and synthetic (man-made)

Natural Polymer Examples Nucleic Acids Examples: DNA, RNA Carbohydrates Examples: starches, sugars Enzymes (protein catalysts that speed up chemical reactions) Example: lactase Vitamins (naturally in plants & animals) Insulin (naturally made in your body)

Synthetic Polymer Examples Plastics (made from petrochemicals) Examples: polystyrene, Styrofoam, polyvinyl chloride (PVC), nylon Kevlar (used in ballistic vests and combat helmets) Pharmaceuticals First synthetic pharmaceutical was aspirin