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Organic Chemistry!!! Chapters 22, 23 and 24 Organic Chemistry The study of carbon and carbon compounds MUCH more abundant than inorganic compounds BONDING Organic Compounds bond covalently Share electrons Form molecules MORE BONDING Carbon atoms bond to one another in: Chains: C-C-C-C-C-C Rings: Networks: Even More Bonding Carbon atoms have 4 valence electrons EN=2.6 (forms mostly covalent bonds) Shares 4 electrons with other atoms to attain octet Types of Covalent Bonds Carbon atoms may form: Single bonds Double bonds Triple bonds Structural Formulas Represents the arrangement of atoms in a compound Indicates bonding pattern and shapes CH4 CH3OH CH3CH2CH2OH Tetrahedral shape-CH4: 4 bonds spread out to the 4 corners ISOMERS Compounds with same molecular formula, but different structural formulas Same # and type of atoms, different arrangement (bonding patterns different) ISOMERS C3H6O (molecular formula) CH3COCH3 CH3CH2CHO (structural formulas) HYDROCARBONS Compounds that contain only C and H atoms Saturated: contain only single bonds Unsaturated: contain at least 1 multiple bond (double or triple) Homologous Series of Hydrocarbons TABLE Q Group of organic compounds with similar properties and related structures Homologous Series The formulas of members of a h. s. differ from each other by some common increment As molecular size increases, increase weak imf, increase b.p., increase f.p. (harder to melt) ALKANES Single bonds only (saturated) Table Q: CnH2n+2 Prefix: # of carbons in longest chain (Table P) Ending: -ane Isomers show up starting with C4H10 butane ALKENES One double bond between carbons (unsaturated) Table Q: CnH2n Prefix: Table P (# of C in longest chain) Ending: -ene Position of the double bond may vary (isomers) Alkenes Longest chain is numbered, starting at end closest to double bond The lower # of C with double bond precedes the name of the hydrocarbon ALKYNES One triple bond between carbons (unsaturated) Table Q: CnH2n-2 Prefix: Table P (# C in longest C chain) Ending: -yne Position of the triple bond may vary (isomers) Alkynes Longest chain is numbered, starting at end closest to triple bond Lower # of the C with triple bond precedes the name of the hydrocarbon Other Organic CompoundsTable R Replace 1 or more hydrogen atoms with other element or group Replacement is called a functional group HALIDES (Group 17) R-X Replace H in a hydrocarbon with halogen Halogen name is shortened to end in -o There can be more than 1 halogen added to a hydrocarbon (replace more than 1 H) Prefixes to indicate number ALCOHOLS Functional group: -OH (R-OH) -OH is alcohol in organic, base in inorganic Alcohol: does not form hydroxide ion in solution; not an ionic compound but a molecule Naming Alcohols Number of C attached to it (if 3 or more C) Name hydrocarbon first Replace final -e with -ol Classes of alcohols: Monohydroxy: one -OH group Dihydroxy: two -OH groups Trihydroxy: three -OH groups 1-propanol Ethers Functional Group: -O- ; R1-O-R2 Diethyl ether (solvent and anesthetic) C2H5OC2H5 Methyl ethyl ether CH3OCH2CH3 diethylether Methyl ethyl ether ALdehydes H Functional group: -C=O Naming: replace the -e of hydrocarbon with -al Only one available bonding site, usually found at end of chain Methanal (formaldehyde) ketones Naming: replace the ending -e with -one Simplest ketone is when R1 and R2 are methyl groups (-CH3) Ketones are isomers of aldehydes (ketones have 2 R groups, aldehydes 1 R) ketONEs Propanone (acetone) OrganIC ACID Functional Group: -COOH To name organic acids Replace ending -e with -oic acid Methanoic acid: Ester COOCR’ is named first (group attached to the -O-), -e is replaced with -yl R is named next (group attached to -C) -e is replaced by -oate Methyl ethanoate Amine Naming: drop the -e and replace with -amine Amides Combines a carbonyl (double bonded oxygen) and an amine on the same C. Amides Naming: replace -e with -amide General Characteristics of Organic Compounds molecular compounds (contrast with ionic compounds) NONPOLAR (mostly) Few dissolve in water (polar) Vinegar (acetic acid) Various sugars and alcohols (all have -OH like water) More characteristics Nonelectrolytes Not ionic COOH (organic acids) are weak electrolytes Low melting points (weak IMFs) Slow reaction rates High Ea needed Catalysts used Covalent bonds are strong (harder to break) Organic Reactions Organic reactions occur at much slower rates than inorganic reactions In an organic reaction, the functional groups are usually involved TABLE R!!! Combustion Saturated hydrocarbon + O2 CO2 + H2O + heat Energy derived by combustion and cellular respiration Oxidation reactions (oxygen involved) Substitution Occurs in saturated hydrocarbons (alkanes) Replace a hydrogen with another element or group More than 1 product is typical Substitution Ethane + bromine bromoethane + hydrogen bromide C2H6 + Br2 C2H5Br + HBr Addition Adding two or more atoms to C-atoms in unsaturated hydrocarbons Usually saturates the bond makes a single bond Takes place more easily than substitution reactions Unsaturated compounds more reactive than saturated compounds Addition continued Triple bonds (alkynes) more reactive than double bonds (alkenes) Reactivity: alkynes > alkenes > alkanes Addition of H= hydrogenation Requires a catalyst and elevated temperature “partially hydrogenated oils” Characterized by the formation of a single product Fermentation Molecules broken down Alcohol production (CO2 made alsocarbonation) Usually associated with living organisms Yeast Enzymes serve as catalysts Fermentation Example Fermentation of Glucose Zymasemade by yeast Esterification Organic acid + alcohol ester + water Esters have a first and last name (R’ and R) R’= first name: alcohol name with -yl ending R= last name: organic acid name with -oate ending Example: ethanoic acid + methanol --> methyl ethanoate + water Esters Are responsible for aromas Fruits, flowers, leaves Lipids (fats and oils) are esters Made from glycerol and fatty acids Compared to inorganic process of neutralization (Acid + Base salt + water) Saponification Making soap Animal fat + base soap + glycerol Hydrolysis of fats (complex esters) by bases Break apart esters Reverse of esterification Break esters into acid and alcohol Polymerization Make a long chain (polymer) by bonding smaller chains (monomers) Plastics, nylon, rayon, proteins, starches, cellulose Two types of polymerization: Condensation Addition Condensation Bond monomers by dehydration (removing water) Monomer + monomer polymer + H2O Addition Join monomers of unsaturated compounds by “opening” a multiple bond of the carbon chain