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A Crash Course In Organic Chemistry

A Crash Course In Organic Chemistry. Organic Chem. Study of organic chemistry and life Study of organic compounds in life Study of hydrocarbon compounds in and their uses in life . Alkanes (C n H 2n+2 ). Naming Branched Alkanes. Find the longest carbon chain and name alkane

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A Crash Course In Organic Chemistry

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  1. A Crash Course In Organic Chemistry

  2. Organic Chem • Study of organic chemistry and life • Study of organic compounds in life • Study of hydrocarbon compounds in and their uses in life

  3. Alkanes (CnH2n+2)

  4. Naming Branched Alkanes • Find the longest carbon chain and name alkane • Number the carbon from the end with nearest substituent (side group) • Determine the name of substituent and add –yl; halogens are chloro, fluoro, iodo • Put the names in alphabetical order • Identify the positions of all substituents in the name by placing the carbon number where the substituent attaches to the parent chain in front of it. • Arrange in alphabetical order and list each one

  5. Naming 2,2,4-trimethyl-3-propylhexane 3-ethyl-3-methyl-4,5-dipropyloctane 6-ethyl-4,5-dipropylnonane

  6. Naming http://www.sciencegeek.net/APchemistry/APtaters/alkanes.htm 2,2,3-trimethylpentane 4-ethyl-3-methyl-4-propyloctane 4,4-diethyl-2,3-dimethylheptane

  7. Reactions of Alkanes • Combustion: reaction with O2 in the • presence of sparks Natural gas CH4(g) + 2 O2(g)                     CO2(g) + 2 H2O(g) disposable cigarette lighters 2 C4H10(g) + 13 O2(g)                     8 CO2(g) + 10 H2O(g) charcoal lighter fluid C5H12(g) + 8 O2(g)                     5 CO2(g) + 6 H2O(g) hydrocarbons in gasoline 2 C8H18(l) + 25 O2(g)                      16 CO2(g) + 18 H2O(g)

  8. 2. Halogenation: reaction with halogens (I, Br, F, Cl) to form alkyl halides In the presence of light, or at high temperatures, alkanes react with halogens to form alkyl halides:

  9. Halogenation • A substitution reaction where H is substituted by a halogen • The reactivity of the halogens is F2>Cl2>Br2>I2 • The reaction of halogen with methane or ethane will form on product since the reactivity of all of the hydrogens is exactly the same C2H6 C2H5-Cl + HCl

  10. Halogenation • Halogenation of propane up to decane generate more than one alkyl halides since the Hs in the alkanes exhibit different reactivities to halogen • The reactivity of the Hs: 3o >2o >1o 1o- a C bound to one C 2o- a C bound to two C 3o- a C bound to three C H CH3-C-CH2-CH3 CH3

  11. Halogenation • Halogenation of an alkane with more than one type of H will generate more than one alkyl halide called isomers • Same chemical formula but different structures CH3-CH2-CH3   +   Cl2   ——>  45% CH3-CH2-CH2Cl   +   55% CH3-CHCl-CH3 CH3-CH2-CH3   +   Br2  ——>  3% CH3-CH2-CH2Br   +   97% CH3-CHBr-CH3 (CH3)3CH   +   Cl2   ——>  65% (CH3)3CCl   +   35% (CH3)2CHCH2Cl

  12. Alkenes (CnH2n)

  13. Naming Alkenes • Name the longest carbon chain that contains the double bond • The name for the alkenes ends in ene instead of –ane • Number the main chain from the end nearest the double bond. • Indicate the position of the double bond with the number of the first unsaturated carbon. • Place the number and names of substituents in front of the alkene name. • Cyclic alkenes are named as cycloalkenes.

  14. Naming Alkenes 2-methyl-2-pentene 3-methyl-1-pentene

  15. Reactions of Alkenes

  16. Alkynes (CnH2n-2)

  17. Naming Alkynes • Name the longest carbon chain that contains the triple bond • The name for the alkenes ends in yne instead of –ane • Number the main chain from the end nearest the triple bond. • Indicate the position of the triple bond with the number of the first unsaturated carbon. • Place the number and names of substituents in front of the alkyne name.

  18. Reactions of Alkynes

  19. Derivatives of Hydrocarbons • A functional group is a reactive portion of a molecule that undergoes predictable reactions. • All other organic compounds can be considered to be derivatives of hydrocarbons

  20. Organic Functional Gps

  21. Organic Compounds Containing Oxygen • Many of the important functional groups in organic compounds contain oxygen • Examples are • alcohols • ethers • aldehydes • ketones • carboxylic acids • esters

  22. Alcohols • An alcohol is a compound obtained by substituting a hydroxyl group (-OH) for a –H atom on a carbon atom of a hydrocarbon group. • Some examples are methanol ethanol 2-propanol

  23. Alcohols • An ether is a compound with an oxygen “bridge” between two alkyl groups. • An example is diethyl ether

  24. An aldehyde is a compound containing a carbonyl group with at least one H atom attached to it. • An example is ethanal

  25. A ketone is a compound containing a carbonyl group with two hydrocarbon groups attached to it. • An example is 2-butanone

  26. A carboxylic acid is a compound containing the carboxyl group, -COOH. • An example is ethanoic acid

  27. An ester is a compound formed from a carboxylic acid, RCOOH, and an alcohol, R’OH. • The general structure is

  28. Most organic bases are amines, which are compounds that are structurally derived by replacing one or more hydrogen atoms of ammonia with hydrocarbon groups. primary amine secondary amine tertiary amine

  29. Amides are compounds derived from the reaction of ammonia, or of a primary or secondary amine, with a carboxylic acid. • The general formula for a common amide is

  30. Aromatic Compounds • ring compounds: bonds alternate between single & double ones (bonds actually resonate) • most common is benzene • when one hydrogen is replaced: name by placing the name of the substituent first, followed by -benzene • when two hydrogens replaced: ortho (o-), meta (m-) or para (p-) used • when more hydrogens replaced: use numbering system for positions on the

  31. Benzene benzene naphthalene

  32. Polycyclic Aromatic Hydrocarbons (PAHs) • two or more benzene rings fused together, sharing pairs of carbon atoms • PNAs: polynuclear aromatic compounds • PCBs: Polychlorinated biphenyls • PCDDs: Polychlorinated dibenzodioxins • PCDFs: Polychlorinated dibenzofurans anthracene

  33. General Anesthetics

  34. Ether and Chloroform • These agents are the anesthetics from hell • Have negative side effects • Flammable and very toxic CH3-CH2-O-CH2-CH3

  35. Non Halogenated Hydrocarbons • all of these will work, and the longer the chain, the higher the potency. • However, they have a tendency to produce cardiovascular toxicity. • Cyclopropane (U.S.P.) is the only one still in use, and it is explosive.

  36. Ethers • Like hydrocarbons, the longer the chain, the more potent the anesthetic. • However, increasing chain length also increases toxicity and reduces induction time. • Ethyl ether is seldom used, and divinyl ether is explosive and produces deep anesthesia too quickly. CH3-CH2-O-CH2-CH3

  37. Halogenated Hydrocarbons-Cl • Addition of a halogen can reduce or eliminate flammability, and can also increase potency. • Depending on the halogen, some of these compounds can cause arrhythmias and/or renal or hepatic toxicity. • Compounds containing only bromine are generally not useful. Compounds containing only chlorine are subject to limited use, are toxic, and can cause arrhythmias. • The best of the chlorinated agents are ethyl chloride and trichloroethylene

  38. Chlorinated ethylchloride trichloroethylene

  39. Halogenated-F • Fluorinated hydrocarbons are the most useful of the general anesthetics • Were first discovered as offshoots of the nuclear weapons program • Addition of a fluorine decreases flammability, boiling point and the incidence of catechol-induced arrhythmias (these increase as the size of the halogen increases, and F is the smallest halogen). • The structures of a few representative fluorinated hydrocarbon general anesthetics are shown

  40. HalogenatedChlorinated and Fluorinated (these are inhaled) isoflurane halothane sevoflurane enflurane desflurane

  41. Fluorinated • Halothane, USP (Fluothane) - the first fluorinated hydrocarbon to be introduced, is a poor muscle relaxant, and has some toxicity and propensity to cause catechol-induced arrhythmias. • Methoxyflurane (Penthrane) - this analog is somewhat better, but still causes some arrhythmias and other toxicity. It also causes a slow induction period. • Enflurane, U.S.P. (Enthrane) - good anesthetic, but has unsatisfactory analgesia in Stage I. • Isoflurane (Forane) - the best general anesthetic so far, it has no commonly observed ill effects.

  42. Nitrous Oxide • This is the least toxic anesthetic • It is the least potent anesthetic • It causes good analgesia, but is a poor muscle relaxant. • It is an NMDA receptor antagonist so prevent transmission of signals between neurons in the brain N2O

  43. Barbiturates (IV) • Derivatives of barbit acid • act as central nervous system depressants, produce a wide spectrum of effects, from mild sedation to anesthesia • Activate the GABA receptor. GABA is the principal inhibitory neurotransmitter in the mammalianCentral Nervous System (CNS). Barbituric acid Na thiopental Methohexital

  44. Benzodiazepines (IV) • Psychoactive drugs • Used before certain medical procedures such as endoscopies or dental work and prior to some unpleasant medical procedures in order to induce sedation and amnesia for the procedure • Activates the GABA receptor diazepam lorazepam midazolam

  45. Propofol • a short-acting intravenous anesthetic agent • used for the induction of general anesthesia in adult patients and pediatric patients older than 3 years of age • Activates the GABA receptor-inhibits signal transmission in the brain

  46. Etomidate • short acting intravenous anesthetic agent • used for the induction of general anaesthesia and for sedation for short procedures

  47. Ketamine HCl (IV) • deriv of phencyclidine • acts like a volatile anesthetic agent • It is potent, rapid acting and has a short duration • Patients older than 16 will often (27%) have wild dreams and hallucinations during emergence, and so only indicated for children less than 16 years old. • NMDA receptor antagonist

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