A Crash A Crash Course In Course In Organic Organic

ChemistryChemistry

Organic ChemOrganic Chem

Study of organic chemistry and lifeStudy of organic chemistry and life Study of organic compounds in lifeStudy of organic compounds in life Study of hydrocarbon compounds in Study of hydrocarbon compounds in

and their uses in life and their uses in life

Alkanes (CAlkanes (CnnHH2n+22n+2))Number of Carbons

Prefix Structure

1 Methane CH4

2 Ethane CH3CH3

3 Propane CH3CH2CH3

4 Butane CH3(CH2)2CH3

5 Pentane CH3(CH2)3CH3

6 Hexane CH3(CH2)4CH3

7 Heptane CH3(CH2)5CH3

8 Octane CH3(CH2)6CH3

9 Nonane CH3(CH2)7CH3

10 Decane CH3(CH2)8CH3

11 Undecane CH3(CH2)9CH3

12 Dodecane CH3(CH2)10CH3

Naming Branched Naming Branched AlkanesAlkanes

Find the longest carbon chain and name Find the longest carbon chain and name alkanealkane

Number the carbon from the end with nearest Number the carbon from the end with nearest substituent (side group) substituent (side group)

Determine the name of substituent and add –Determine the name of substituent and add –yl; halogens are chloro, fluoro, iodo 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 Identify the positions of all substituents in the

name by placing the carbon number where the name by placing the carbon number where the substituent attaches to the parent chain in substituent attaches to the parent chain in front of it.front of it.

Arrange in alphabetical order and list each one Arrange in alphabetical order and list each one

NamingNaming

2,2,4-trimethyl-3-propylhexane

3-ethyl-3-methyl-4,5-dipropyloctane

6-ethyl-4,5-dipropylnonane

NamingNaming

4-ethyl-3-methyl-4-propyloctane 2,2,3-trimethylpentane

4,4-diethyl-2,3-dimethylheptane

http://www.sciencegeek.net/APchemistry/APtaters/alkanes.htm

Reactions of AlkanesReactions of Alkanes

Natural gasCH4(g) + 2 O2(g)                     CO2(g) + 2 H2O(g)

disposable cigarette lighters2 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)

1.Combustion: reaction with O2 in the presence of sparks

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

react with halogens to form alkyl halides:

light

CH4(g) + Cl2(g)            CH3Cl(g) + HCl(g)

light

CH4(g) + Br2(l)            CH3Br(g) + HBr(g)

HalogenationHalogenation A substitution reaction where H is A substitution reaction where H is

substituted by a halogensubstituted by a halogen The reactivity of the halogens isThe reactivity of the halogens is

FF22>Cl>Cl22>Br>Br22>I>I22 The reaction of halogen with The reaction of halogen with

methane or ethane will form on methane or ethane will form on product since the reactivity of all of product since the reactivity of all of the hydrogens is exactly the samethe hydrogens is exactly the same

CC22HH66 C C22HH55-Cl + HCl-Cl + HCl

HalogenationHalogenation Halogenation of propane up to decane Halogenation of propane up to decane

generate more than one alkyl halides generate more than one alkyl halides since the Hs in the alkanes exhibit since the Hs in the alkanes exhibit different reactivities to halogendifferent reactivities to halogen

The reactivity of the Hs:The reactivity of the Hs:

33oo > >22oo > >11oo

CH3-C-CH2-CH3H

CH3

1o- a C bound to one C2o- a C bound to two C3o- a C bound to three C

HalogenationHalogenation Halogenation of an alkane with more Halogenation of an alkane with more

than one type of H will generate more than one type of H will generate more than one alkyl halide called than one alkyl halide called isomersisomers

Same chemical formula but different Same chemical formula but different structuresstructures

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

Alkenes (CAlkenes (CnnHH2n2n))Number of Carbons Prefix Structure

2 Ethene CH2=CH2

3 Propene CH2=CHCH3

4 Butene CH2=CHCH2CH3

5 Pentene CH2=CH(CH2)2CH3

6 Hexene CH2=CH(CH2)3CH3

7 Heptene CH2=CH(CH2)4CH3

8 Octene CH2=CH(CH2)5CH3

9 Nonene CH2=CH(CH2)6CH3

10 Decene CH2=CH(CH2)7CH3

11 Undecene CH2=CH(CH2)8CH3

12 Dodecene CH2=CH(CH2)9CH3

Naming AlkenesNaming Alkenes1.Name the longest carbon chain that

contains the double bond2.The name for the alkenes ends in ene

instead of –ane3.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.

Naming AlkenesNaming Alkenes

2-methyl-2-pentene

CH2CHCHCH2CH3

CH3

3-methyl-1-pentene

Reactions of AlkenesReactions of AlkenesREACTANT REACTION EXAMPLE

H2 Hydrogenation(catalyzed by metals)

CH2=CH2 → H-CH2-CH2-H

H2O Hydration(catalyzed by acid)

CH2=CH2 → H-CH2-CH2-OH

X2 Halogenation CH2=CH2 → Cl-CH2-CH2-Cl

HX Hydro-halogenation

CH2=CH2 → Cl-CH2-CH2-H

KmnO4,

H2O, and

OH-

Oxidation CH2=CH2 → OH-CH2-CH2-OH

Alkynes (CAlkynes (CnnHH2n-22n-2))Number of Carbons Prefix Structure

2 Ethyne CHΞCH

3 Propyne CHΞCCH3

4 Butyne CHΞCCH2CH3

5 Pentyne CH ΞC(CH2)2CH3

6 Hexyne CH ΞC(CH2)3CH3

7 Heptyne CH ΞC(CH2)4CH3

8 Octyne CH ΞC(CH2)5CH3

9 Nonyne CH ΞC(CH2)6CH3

10 Decyne CH ΞC(CH2)7CH3

11 Undecyne CH ΞC(CH2)8CH3

12 Dodecyne CH ΞC(CH2)9CH3

Naming AlkynesNaming 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.

REACTANT REACTION EXAMPLE

H2 Hydrogenation(catalyzed by metals)

CHΞCH → CH2=CH2

H2O Hydration(catalyzed by acid)

CHΞCH → CH2=CH-OH

X2 Halogenation CHΞCH → Cl-CH=CH-Cl

HX Hydro-halogenation

CHΞCH → Cl-CH=CH2

KmnO4,

H2O, and

OH-

Oxidation CHΞCH → OH-CH=CH-OH

Reactions of AlkynesReactions of Alkynes

Derivatives of Derivatives of HydrocarbonsHydrocarbons

A A functional groupfunctional group is a reactive is a reactive portion of a molecule that portion of a molecule that undergoes predictable reactions.undergoes predictable reactions.

All other organic compounds can All other organic compounds can be considered to be be considered to be derivatives derivatives of hydrocarbonsof hydrocarbons

Organic Functional GpsOrganic Functional Gps

Organic Compounds Organic Compounds Containing OxygenContaining Oxygen

Many of the important functional Many of the important functional groups in organic compounds groups in organic compounds contain oxygencontain oxygen Examples are Examples are

alcohols alcohols ethers ethers aldehydes aldehydes ketones ketones carboxylic acidscarboxylic acids estersesters

An An alcoholalcohol is a compound is a compound obtained by substituting a hydroxyl obtained by substituting a hydroxyl group (-OH) for a –H atom on a group (-OH) for a –H atom on a carbon atom of a hydrocarbon carbon atom of a hydrocarbon group.group.•Some examples

are CH3 OH CH2CH3 OH CH3CHCH3

OH

methanol ethanol 2-propanol

AlcoholsAlcohols

AlcoholsAlcohols An An etherether is a compound with an is a compound with an

oxygen “bridge” between two alkyl oxygen “bridge” between two alkyl groups.groups.

•An example is

O CH2 CH3CH2CH3

diethyl ether

An An aldehydealdehyde is a compound is a compound containing a carbonyl group with containing a carbonyl group with at least one H atom attached to it.at least one H atom attached to it.

•An example is

ethanal

CHCH3

O

A A ketoneketone is a compound containing is a compound containing a carbonyl group with two a carbonyl group with two hydrocarbon groups attached to it.hydrocarbon groups attached to it.

•An example is

2-butanone

CH3CCH2CH3

O

A A carboxylic acidcarboxylic acid is a compound is a compound containing the carboxyl group, -COOH.containing the carboxyl group, -COOH.

•An example is

ethanoic acid

CCH3 OH

O

An An esterester is a compound formed is a compound formed from a carboxylic acid, RCOOH, from a carboxylic acid, RCOOH, and an alcohol, R’OH.and an alcohol, R’OH.

•The general structure is

CR O

O

R'

Most organic bases are Most organic bases are aminesamines, , which are compounds that are which are compounds that are structurally derived by replacing structurally derived by replacing one or more hydrogen atoms of one or more hydrogen atoms of ammonia with hydrocarbon groups.ammonia with hydrocarbon groups.

NH

H

R NH

R'

R NR"

R'

R

primary amine secondary amine tertiary amine

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

•The general formula for a common amide is

CR N

O

H

H

G rou p in g s o f O rg an ic C om p ou n d s

A lip h a tic com p ou n d scon ta in s tra ig h t o r b ran c h ed ch a in s o rrin g s con ta in in g s in g le c a rb on b on d s

A rom atic com p ou n d scarb on -b ased rin g s o r m u lt i-rin g s w ith

a lte rn a tin g s in g le & d ou b le ca rb on b on d s

O rg an ic C om ou n d s

ring compounds: bonds alternate ring compounds: bonds alternate between single & double ones (bonds between single & double ones (bonds actually resonate)actually resonate)

most common is benzenemost common is benzene when one hydrogen is replaced: name when one hydrogen is replaced: name

by placing the name of the substituent by placing the name of the substituent first, followed by -benzenefirst, followed by -benzene

when two hydrogens replaced: ortho when two hydrogens replaced: ortho (o-), meta (m-) or para (p-) used(o-), meta (m-) or para (p-) used

when more hydrogens replaced: use when more hydrogens replaced: use numbering system for positions on thenumbering system for positions on the

Aromatic CompoundsAromatic Compounds

benzene

naphthalene

BenzeneBenzene

Polycyclic Aromatic Polycyclic Aromatic Hydrocarbons (PAHs)Hydrocarbons (PAHs)

two or more benzene rings fused two or more benzene rings fused together, sharing pairs of carbon atomstogether, sharing pairs of carbon atoms

PNAs: polynuclear aromatic compoundsPNAs: polynuclear aromatic compounds PCBs: Polychlorinated biphenylsPCBs: Polychlorinated biphenyls PCDDs: Polychlorinated dibenzodioxinsPCDDs: Polychlorinated dibenzodioxins PCDFs: Polychlorinated dibenzofuransPCDFs: Polychlorinated dibenzofurans

anthracene

General Anesthetics

Ether and ChloroformEther and Chloroform

These agents are the These agents are the anesthetics anesthetics from hellfrom hell

Have negative side effectsHave negative side effects Flammable and very toxicFlammable and very toxic

CH3-CH2-O-CH2-CH3

Non Halogenated Non Halogenated HydrocarbonsHydrocarbons

all of these will work, and the longer all of these will work, and the longer the chain, the higher the potency. the chain, the higher the potency.

However, they have a tendency to However, they have a tendency to produce cardiovascular toxicity. produce cardiovascular toxicity.

Cyclopropane (U.S.P.) is the only one Cyclopropane (U.S.P.) is the only one still in use, and it is explosive. still in use, and it is explosive.

EthersEthers Like hydrocarbons, Like hydrocarbons, the longer the the longer the

chain, the more potent the chain, the more potent the anestheticanesthetic. .

However, increasing chain length also However, increasing chain length also increases toxicity and reduces increases toxicity and reduces induction time. induction time.

Ethyl ether is seldom used, and divinyl Ethyl ether is seldom used, and divinyl ether is explosive and produces deep ether is explosive and produces deep anesthesia too quickly. anesthesia too quickly.

CH3-CH2-O-CH2-CH3

Halogenated Hydrocarbons-Halogenated Hydrocarbons-ClCl

Addition of a halogen can reduce or Addition of a halogen can reduce or eliminate flammability, and can also eliminate flammability, and can also increase potency. increase potency.

Depending on the halogen, some of these Depending on the halogen, some of these compounds can cause compounds can cause arrhythmiasarrhythmias and/or and/or renal or hepatic renal or hepatic toxicitytoxicity. .

Compounds containing only bromine are Compounds containing only bromine are generally not useful. Compounds containing generally not useful. Compounds containing only chlorine are subject to limited use, are only chlorine are subject to limited use, are toxic, and can cause arrhythmias. toxic, and can cause arrhythmias.

The best of the chlorinated agents are ethyl The best of the chlorinated agents are ethyl chloride and trichloroethylene chloride and trichloroethylene

ChlorinatedChlorinated

ethylchloride trichloroethylene

Halogenated-FHalogenated-F Fluorinated hydrocarbons are the most Fluorinated hydrocarbons are the most

useful of the general anestheticsuseful of the general anesthetics Were first discovered as offshoots of the Were first discovered as offshoots of the

nuclear weapons programnuclear weapons program Addition of a fluorine decreases Addition of a fluorine decreases

flammability, boiling point and the flammability, boiling point and the incidence of catechol-induced incidence of catechol-induced arrhythmias (these increase as the size arrhythmias (these increase as the size of the halogen increases, and F is the of the halogen increases, and F is the smallest halogen). smallest halogen).

The structures of a few representative The structures of a few representative fluorinated hydrocarbon general fluorinated hydrocarbon general anesthetics are shownanesthetics are shown

HalogenatedHalogenatedChlorinated and Chlorinated and

FluorinatedFluorinated

halothane

enflurane

isoflurane

sevoflurane

desflurane

(these are inhaled)

FluorinatedFluorinated Halothane, USP (Fluothane) - the first fluorinated Halothane, USP (Fluothane) - the first fluorinated

hydrocarbon to be introduced, is a poor muscle hydrocarbon to be introduced, is a poor muscle relaxant, and has some toxicity and propensity relaxant, and has some toxicity and propensity to cause catechol-induced arrhythmias. to cause catechol-induced arrhythmias.

Methoxyflurane (Penthrane) - this analog is Methoxyflurane (Penthrane) - this analog is somewhat better, but still causes some somewhat better, but still causes some arrhythmias and other toxicity. It also causes a arrhythmias and other toxicity. It also causes a slow induction period. slow induction period.

Enflurane, U.S.P. (Enthrane) - good anesthetic, Enflurane, U.S.P. (Enthrane) - good anesthetic, but has unsatisfactory analgesia in Stage I. but has unsatisfactory analgesia in Stage I.

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

Nitrous OxideNitrous Oxide This is the least toxic anestheticThis is the least toxic anesthetic It is the least potent anestheticIt is the least potent anesthetic It causes good analgesia, but is a It causes good analgesia, but is a

poor muscle relaxant.poor muscle relaxant. It is an NMDA receptor antagonist so It is an NMDA receptor antagonist so

prevent transmission of signals prevent transmission of signals between neurons in the brainbetween neurons in the brain

N2O

Barbiturates (IV)Barbiturates (IV)

               Methohexital

Methohexital Na thiopental

Barbituric acid

Derivatives of barbit acidDerivatives of barbit acid act as central nervous act as central nervous

system system depressantsdepressants, , produce a wide spectrum produce a wide spectrum of effects, from mild of effects, from mild sedationsedation to to anesthesiaanesthesia

Activate the GABA Activate the GABA receptor. GABA is the receptor. GABA is the principal inhibitory principal inhibitory neurotransmitter in the neurotransmitter in the mammalian Central mammalian Central Nervous System (CNS).Nervous System (CNS).

Benzodiazepines (IV)Benzodiazepines (IV)

midazolam lorazepam

diazepam

Psychoactive drugsPsychoactive drugs Used before certain Used before certain

medical procedures medical procedures such as endoscopies or such as endoscopies or dental work and prior dental work and prior to some unpleasant to some unpleasant medical procedures in medical procedures in order to induce order to induce sedation and amnesia sedation and amnesia for the procedurefor the procedure

Activates the GABA Activates the GABA receptorreceptor

PropofolPropofola short-acting a short-acting intravenous intravenous anesthetic agent anesthetic agent used for the used for the induction of general induction of general anesthesia in adult anesthesia in adult patients and patients and pediatric patients pediatric patients older than 3 years older than 3 years of ageof ageActivates the GABA Activates the GABA receptor-inhibits receptor-inhibits signal transmission signal transmission in the brainin the brain

EtomidateEtomidateshort acting intravenous anesthetic agent used for the induction of general anaesthesia and for sedation for short procedures

Ketamine HCl (IV)Ketamine HCl (IV) deriv of phencyclidinederiv of phencyclidine acts like a volatile acts like a volatile

anesthetic agentanesthetic agent It is potent, rapid acting It is potent, rapid acting

and has a short durationand has a short duration Patients older than 16 will Patients older than 16 will

often (27%) have wild often (27%) have wild dreams and hallucinations dreams and hallucinations during emergence, and so during emergence, and so only indicated for children only indicated for children less than 16 years old.less than 16 years old.

NMDA receptor antagonist NMDA receptor antagonist

Local Anesthetics

Local AnestheticsLocal Anesthetics

Local anesthetics are agents which Local anesthetics are agents which prevent transmission of nerve prevent transmission of nerve impulses without causing impulses without causing unconsciousness. unconsciousness.

They act by binding to fast They act by binding to fast sodium channelssodium channels from within (in an from within (in an open state). open state).

Local anesthetics can be either Local anesthetics can be either esterester or or amideamide based. based.

Local AnestheticsLocal Anesthetics

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

Amino EstersAmino Esters

cocaine

procaine

tetracaine

chloroprocaine

Amino AmidesAmino Amides

bupivicaine cinchocaine

levobupivicaine lidocaine

prilocaine

ropivacaine

Common Local Common Local AnestheticsAnesthetics

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 45 - 2.8 -

Procaine 15-30 30-90 7.1 8.5

Chloroprocaine 30-60 - 11.4 14.2

Tetracaine 120-240 240-480 1.4 -

Amides

Lidocaine 30-120 60-400 4.5 7

Mepivacaine 30-120 30-120 4.5 7

Bupivacaine 120-240 240-480 2.5 3.2

Etidocaine 200 240-360 4.2 5.7

Prilocaine 30-120 60-400 5.7 8.5