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A Crash Course In Organic Chemistry. Organic Chem Study of organic chemistry and life Study of organic chemistry and life Study of organic compounds in.

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Presentation on theme: "A Crash Course In Organic Chemistry. Organic Chem Study of organic chemistry and life Study of organic chemistry and life Study of organic compounds in."— Presentation transcript:

1 A Crash Course In Organic Chemistry

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

3 Alkanes (C n H 2n+2 ) Number of Carbons PrefixStructure 1MethaneCH 4 2EthaneCH 3 3PropaneCH 3 CH 2 CH 3 4ButaneCH 3 (CH 2 ) 2 CH 3 5PentaneCH 3 (CH 2 ) 3 CH 3 6HexaneCH 3 (CH 2 ) 4 CH 3 7HeptaneCH 3 (CH 2 ) 5 CH 3 8OctaneCH 3 (CH 2 ) 6 CH 3 9NonaneCH 3 (CH 2 ) 7 CH 3 10DecaneCH 3 (CH 2 ) 8 CH 3 11UndecaneCH 3 (CH 2 ) 9 CH 3 12DodecaneCH 3 (CH 2 ) 10 CH 3

4 Naming Branched Alkanes Find the longest carbon chain and name alkane Find the longest carbon chain and name alkane Number the carbon from the end with nearest substituent (side group) Number the carbon from the end with nearest substituent (side group) Determine the name of substituent and add –yl; halogens are chloro, fluoro, iodo Determine the name of substituent and add –yl; halogens are chloro, fluoro, iodo Put the names in alphabetical order 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. 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 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 4-ethyl-3-methyl-4-propyloctane 2,2,3-trimethylpentane 4,4-diethyl-2,3-dimethylheptane

7 Reactions of Alkanes Natural gas CH 4 (g) + 2 O 2 (g) CO 2 (g) + 2 H 2 O(g) disposable cigarette lighters 2 C 4 H 10 (g) + 13 O 2 (g) 8 CO 2 (g) + 10 H 2 O(g) charcoal lighter fluid C 5 H 12 (g) + 8 O 2 (g) 5 CO 2 (g) + 6 H 2 O(g) hydrocarbons in gasoline 2 C 8 H 18 (l) + 25 O 2 (g) 16 CO 2 (g) + 18 H 2 O(g) 1.Combustion: reaction with O 2 in the presence of sparks

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: light CH 4 (g) + Cl 2 (g) CH 3 Cl(g) + HCl(g) light CH 4 (g) + Br 2 (l) CH 3 Br(g) + HBr(g)

9 Halogenation A substitution reaction where H is substituted by a halogen A substitution reaction where H is substituted by a halogen The reactivity of the halogens is The reactivity of the halogens is F 2 >Cl 2 >Br 2 >I 2 F 2 >Cl 2 >Br 2 >I 2 The reaction of halogen with methane or ethane will form on product since the reactivity of all of the hydrogens is exactly the same The reaction of halogen with methane or ethane will form on product since the reactivity of all of the hydrogens is exactly the same C 2 H 6 C 2 H 5 -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 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: The reactivity of the Hs: 3 o >2 o >1 o 3 o >2 o >1 o CH3-C-CH 2 -CH3 H CH 3 1 o - a C bound to one C 2 o- a C bound to two C 3 o - a C bound to three C

11 Halogenation Halogenation of an alkane with more than one type of H will generate more than one alkyl halide called isomers 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 Same chemical formula but different structures CH 3 -CH 2 -CH 3 + Cl 2 ——> 45% CH 3 -CH 2 -CH 2 Cl + 55% CH 3 -CH Cl -CH 3 CH 3 -CH 2 -CH 3 + Br 2 ——> 3% CH 3 -CH 2 -CH 2 Br + 97% CH 3 -CHBr-CH 3 (CH 3 ) 3 CH + Cl 2 ——> 65% (CH 3 ) 3 CCl + 35% (CH 3 ) 2 CHCH 2 Cl

12 Alkenes (C n H 2n ) Number of CarbonsPrefixStructure 2EtheneCH 2 =CH 2 3PropeneCH 2 =CHCH3 4ButeneCH 2 =CHCH 2 CH 3 5PenteneCH 2 =CH(CH 2 ) 2 CH 3 6HexeneCH 2 =CH(CH 2 ) 3 CH 3 7HepteneCH 2 =CH(CH 2 ) 4 CH 3 8OcteneCH 2 =CH(CH 2 ) 5 CH 3 9NoneneCH 2 =CH(CH 2 ) 6 CH 3 10DeceneCH 2 =CH(CH 2 ) 7 CH 3 11UndeceneCH 2 =CH(CH 2 ) 8 CH 3 12DodeceneCH 2 =CH(CH 2 ) 9 CH 3

13 Naming Alkenes 1.Name the longest carbon chain that contains the double bond 2.The name for the alkenes ends in ene instead of –ane 3.Number the main chain from the end nearest the double bond. 4.Indicate the position of the double bond with the number of the first unsaturated carbon. 5.Place the number and names of substituents in front of the alkene name. 6.Cyclic alkenes are named as cycloalkenes.

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

15 Reactions of Alkenes REACTANTREACTIONEXAMPLE H2H2 Hydrogenation (catalyzed by metals) CH 2 =CH 2 → H-CH 2 -CH 2 -H H2OH2OHydration (catalyzed by acid) CH 2 =CH 2 → H-CH 2 -CH 2 -OH X2X2 HalogenationCH 2 =CH 2 → Cl-CH 2 -CH 2 -Cl HXHydro- halogenation CH 2 =CH 2 → Cl-CH 2 -CH 2 -H KmnO 4, H 2 O, and OH - OxidationCH 2 =CH 2 → OH-CH 2 -CH 2 -OH

16 Alkynes (C n H 2n-2 ) Number of CarbonsPrefixStructure 2EthyneCHΞCH 3PropyneCHΞCCH3 4ButyneCHΞCCH 2 CH 3 5PentyneCH ΞC(CH 2 ) 2 CH 3 6HexyneCH ΞC(CH 2 ) 3 CH 3 7HeptyneCH ΞC(CH 2 ) 4 CH 3 8OctyneCH ΞC(CH 2 ) 5 CH 3 9NonyneCH ΞC(CH 2 ) 6 CH 3 10DecyneCH ΞC(CH 2 ) 7 CH 3 11UndecyneCH ΞC(CH 2 ) 8 CH 3 12DodecyneCH ΞC(CH 2 ) 9 CH 3

17 Naming Alkynes 1.Name the longest carbon chain that contains the triple bond 2.The name for the alkenes ends in yne instead of –ane 3.Number the main chain from the end nearest the triple bond. 4.Indicate the position of the triple bond with the number of the first unsaturated carbon. 5.Place the number and names of substituents in front of the alkyne name.

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19 REACTANTREACTIONEXAMPLE H2H2 Hydrogenation (catalyzed by metals) CHΞCH → CH 2 =CH 2 H2OH2OHydration (catalyzed by acid) CHΞCH → CH 2 =CH-OH X2X2 HalogenationCHΞCH → Cl-CH=CH-Cl HXHydro- halogenation CHΞCH → Cl-CH=CH 2 KmnO 4, H 2 O, and OH - OxidationCHΞCH → OH-CH=CH-OH Reactions of Alkynes

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

21 Organic Functional Gps

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

23 An alcohol is a compound obtained by substituting a hydroxyl group (-OH) for a –H atom on a carbon atom of a hydrocarbon group. 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 methanolethanol2-propanol Alcohols

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

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

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

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

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

29 Most organic bases are amines, which are compounds that are structurally derived by replacing one or more hydrogen atoms of ammonia with hydrocarbon groups. 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 aminesecondary aminetertiary amine

30 Amides are compounds derived from the reaction of ammonia, or of a primary or secondary amine, with a carboxylic acid. 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

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32  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 Aromatic Compounds

33 benzene naphthalene Benzene

34 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

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36 General Anesthetics

37 Ether and Chloroform These agents are the anesthetics from hell These agents are the anesthetics from hell Have negative side effects Have negative side effects Flammable and very toxic Flammable and very toxic CH 3 -CH 2 -O-CH 2 -CH 3

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

39 Ethers Like hydrocarbons, the longer the chain, the more potent the anesthetic. Like hydrocarbons, the longer the chain, the more potent the anesthetic. However, increasing chain length also increases toxicity and reduces induction time. 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. Ethyl ether is seldom used, and divinyl ether is explosive and produces deep anesthesia too quickly. CH 3 -CH 2 -O-CH 2 -CH 3

40 Halogenated Hydrocarbons-Cl Addition of a halogen can reduce or eliminate flammability, and can also increase potency. 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. 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. 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 The best of the chlorinated agents are ethyl chloride and trichloroethylene

41 Chlorinated ethylchloride trichloroethylene

42 Halogenated-F Fluorinated hydrocarbons are the most useful of the general anesthetics Fluorinated hydrocarbons are the most useful of the general anesthetics Were first discovered as offshoots of the nuclear weapons program 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). 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 The structures of a few representative fluorinated hydrocarbon general anesthetics are shown

43 Halogenated Chlorinated and Fluorinated halothane enflurane isoflurane sevoflurane desflurane (these are inhaled)

44 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. 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. 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. 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. Isoflurane (Forane) - the best general anesthetic so far, it has no commonly observed ill effects.

45 Nitrous Oxide This is the least toxic anesthetic This is the least toxic anesthetic It is the least potent anesthetic It is the least potent anesthetic It causes good analgesia, but is a poor muscle relaxant. 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 It is an NMDA receptor antagonist so prevent transmission of signals between neurons in the brain N2ON2O

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

47 Benzodiazepines (IV) midazolam lorazepam diazepam Psychoactive drugs 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 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 procedureendoscopiesdental worksedation amnesiaendoscopiesdental worksedation amnesia Activates the GABA receptor Activates the GABA receptor

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

49 Etomidate  short acting intravenous anesthetic agent intravenous  used for the induction of general anaesthesia and for sedation for short proceduresgeneral anaesthesiasedation

50 Ketamine HCl (IV) deriv of phencyclidine deriv of phencyclidine acts like a volatile anesthetic agent acts like a volatile anesthetic agent It is potent, rapid acting and has a short duration 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. 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 NMDA receptor antagonist

51 Local Anesthetics

52 Local Anesthetics Local anesthetics are agents which prevent transmission of nerve impulses without causing unconsciousness. Local anesthetics are agents which prevent transmission of nerve impulses without causing unconsciousness. They act by binding to fast sodium channels from within (in an open state). They act by binding to fast sodium channels from within (in an open state).sodium channelssodium channels Local anesthetics can be either ester or amide based. Local anesthetics can be either ester or amide based.ester amideester amide

53 Local Anesthetics Have the following general structure: Aromatic-benzene ring-hydrophobic Intermediate-amide or ester portion Amino portion-hydrophyllic

54 Amino Esters cocaine procaine tetracaine chloroprocaine

55 Amino Amides bupivicaine cinchocaine levobupivicaine lidocaine prilocaine ropivacaine

56 Common Local Anesthetics Anesthetic Duration w/o Epi, min Duration W/ Epi, min Maximum Dose w/o Epi, mg/kg Maximum Dose W/ Epi, mg/kg Esters Cocaine Procaine Chloroprocaine Tetracaine Amides Lidocaine Mepivacaine Bupivacaine Etidocaine Prilocaine


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