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Hydrocarbons and Functional Groups 96% living matter composed of: OCHN Essential elements for life+health: COHNSP Five essential ions: Na+, K+, Mg2+,Ca2+,Cl- Most common trace elements: Mn, Fe, Co, Cu, Zn Less common trace elements: V, Cr, Mo, Ni, Ga, B, Al, Si, F, As, Se, Sn, I Only about 30 of the 90+ naturally occurring chemical elements are essential to the human body O: 65.0 C: 18.5 H: 9.5 N: 3.3 Ca: 1.5 P: 1.0 K: 0.4 S: 0.3 Na: 0.2 Cl: 0.2 Mg: 0.1 Trace Effects Iodine deficiency: Endemic goiter, dwarfism, mental retardation Iron imbalance: too much = hemochromatosis (cancer of liver); too little = anemia (low lvl of healthy red blood cell or hemoglobin) Hydrocarbon: organic compounds composed of only C and H. Varies in length, branch vs. unbranched, types of bonds, can be arranged in rings Ex: gasoline is mixture of large hydrocarbons; ethane; propane Large hydrocarbons constitute skeletons of fatty acids in food (French fries) Aromatic compound: hydrocarbons or hydrocarbon derivatives containing benzene rings (unsaturated) Ex: benzalhyde, methylbenzene Homologous series: differing by a CH2 unit Structural isomers: same molec. formula, dif. structure ------------------------------------------------------------------------------------------------------------------------------- ----------- Functional groups: a group of specifically linked atoms with characteristic physical and chemical properties 1: meth- 2: eth- 3: prop- 4: but- 5: pent- 6: hex- 7: hept- 8: oct- Ring: cyclo- Branched skeleton: i- (iso) Linear C chains: n- (normal) Aromatic compounds: number starts with first side group Ex: isobutane aka 2-methyl-propane Ex: heptane aka n-heptane Alkyl group: alkane with one H atom removed (ex: methyl-) H replaced by other atom (ex: chloro-) Alkane: saturated hydrocarbon; each c atom in a single covalent bond is tetrahedral - non-cyclic: C(n)H(2n+2) - cyclic: C(n)H(2n) Alkene: unsaturated hydrocarbon; need number where double bond is (bond determines first C) - non-cyclic: C(n)H(2n) - cyclic: C(n)H(2n-2) Alkyne: - general formula: C(n)H(2n-2) Halogenoalkane: -X (F, Cl, Br, I); halogeno- (ex: chloroethane) Alcohol (hydroxyl group): -OH; -anol (hydroxy-) Ether (ether group): R-O-R’; -oxy-ane (ex: methoxy ethane is CH3OCH2CH3) Ester (ester group): R-O-CO-R; alkyl- -alkanoate (ex: methyl ethanoate is CH2COOCH3) Amine (amino group): RNH2/R2NH/R3N; -ylamine/animo- (ex: ethylamine is CH3CH3NH3) Amide (amide group): R-CO-NR2/R-CO-NHR/R-CO-NH2; -anamide (ex: ethanamide is CH3CONH2) Thiol (sulfhydryl group): RSH; -thiol (ex: CH3SH) Aldehyde (carbonyl group): -CHO; -anal Ketone (carbonyl group): -CO; anone Carboxylic acid (carboxyl group): COOH; -anoic acid Nitrate: R-C≡N; -anenitrile/cyano- (ex: CH3CN is ethanenitrile cyanomethane) Rules for Naming 1. find name of longest C chain aka parent chain 2. ID and name atoms/groups attached to parent chain aka substituent (ex: methyl-, bromo-,hydroxyl) 3. determine highest priority substituent: the more O atoms + more multiple bonds = higher priority When multiple functional groups, see step 3 4. find correct suffix based on step 3 5. remember the stupid number 6. list groups in alphabetical order!!! (prefixes like di, tri, tetra do NOT count for alphebatizing) Ex: 3-iodo-2,2-dimethylpentane ------------------------------------------------------------------------------------------------------------------------------- ----------- Lowest boiling pt of the alkanes: ethane Isomers: diff compounds with same molecular formula; same molecular formula, but diff structures, hence diff properties Constitutional (structural): isomers whose atoms have a different connectivity; different connectivity of atoms yields diff classes of organic compounds and/or diff members w/I the same class Structural isomers of alkanes: CH4: 1 C2H6: 1 C3H8: 1 C4H10: 2 C5H12: 3 (pentane; 2-methylbutane; 2,2-dimethylpropane) C6H14: 5 C7H16: 9 C8H18: 18 35, 75, 159, 355, 4347, 366319, 4.1 x 10^9, 6.3 x 10^13 Structural isomer of aromatic compounds 1,2-dimethylbenzene = orthodimethylbenzene 1,3-dimethylbenzene = metadimethylbenzene 1,4-dimethylbenzene = paradimethylbenzene 1,2,3; 1,2,4; 1,3,5 Stereoisomers: isomers that have the same connectivity but that differ in the arraignment of their atoms in space Chemical bond: a balance b/w attractive + repulsive forces b/w 2 atoms Sigma bond: e- density concentrated along the internuclear axis Pi bond: bonding e- density concentrated above and below the internuclear axis Carbon = free rotation around a C-C bond; no rotation around a C=C bond Geometric isomers: stereoisomers determined by restriction of rotation about a double bond Cis: adjacent (mirror image); squiggle Trans: across (rotate 180); half a hexagon Each C in C=C bond has 2 different groups attached ------------------------------------------------------------------------------------------------------------------------------- ----------- Chirality Chiral center: an atom in a molecule that is attached to 4 different atoms or groups Chiral: nonsuperimposable mirror images Enantiomer: type of chiral stereoisomers with identical chemical and physical properties, but different biological + optical ones Achiral molecule: rated molecule can be superimposed on mirror image Interactions b/w biomolecules are complementary Enzyme-substrate Hormone-receptor on cell surface Antigen-antibody Chemical fuel: substance that reacts with O2 (combustion; exothermic) Good fuel: bonds of fuel are weaker; bonds of combustion products are stronger Ex: methane: CH4 + 2O2 = 2H2O + CO2 Ex: Hydrazine: NH2-NH2 + O2 = N2 + 2H2O Change in E = bond E of reactants minus bond E of products Petroleum: mixture of alkanes, cycloalkanes, alkenes, aromatic hydrocarbons Extracted as crude oil; must be refined Gases: below 20C; C1-C4 hydrocarbons; used as fuel and reactants to make plastics Gasoline (naphthas): 20-200C; C5-C12 hydrocarbons; used as motor fuels and industrial solvents) Kerosene: 175-275C; C12-C16; lamp oil, diesel fuel, starting material for catalytic cracking Fuel oil: 250-400C; C15-C18; catalytic cracking, heating oil, diesel fuel Lubricating oil: 350+C; C16-C20; used as lubricants Residue (asphalt): >C20) Octane number: rates a fuel’s ability to burn smoothly; higher number = smoother combustion T(autoignition): the T starting from which hydrocarbons vapors can autoignite Scale: 0 = n-heptane (low T autoignition) 100 = i-octane (high T autoignition) Ex: if 20% heptane and 80% i-octane, octane number i
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