Chem & Physics Chap11 - Organic Chemistry

Front 1

organic chemistry is

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the study of substances containing carbon (4 million compounds)

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most medications and inhalation agents are

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examples of organic compounds

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Inorganic chemistry is

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the study of noncarbon compounds (100,000 compounds)

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example of anesthetic related inorganic compound

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N2O

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carbon molecules that are classified inorganic

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CN-, HCO3-, CO32-

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hydrocarbons

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contain only carbon and hydrogen

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types of hydrocarbons

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aliphatic, alicyclic, aromatic

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types of aliphatic hydrocarbons are

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alkanes, alkenes, alkynes

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aliphatic means

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straight chain

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alicyclic means

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ring structure - but not a benzene ring

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aromatic means

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benzene ring with alternating single and double bonds

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carbon has how many valence electrons

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4

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when carbon bonds to 4 atoms

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tetrahedral structure, 4 single bonds, 109.5 degree angles - methane

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when carbon bonds to 3 atoms

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planar arrangement, 1 double bond and 2 single bonds, bond angles of 120 degree

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when carbon bonds to 2 atoms

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linear arrangement, 1 triple and 2 single bonds, 2 double bonds, bond angle of 180

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alkanes are

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saturated hydrocarbons, aliphatic, CnH2n+2

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methane

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CH4

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Ethane

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C2H6

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Propane

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C3H8

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BUTANE

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C4H10

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PENTANE

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C5H12

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HEXANE

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C6H14

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HEPTANE

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C7H16

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OCTANE

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C8H18

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NONANE

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C9H20

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DECANE

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C10H22

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isomers

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any compound that has the same molecular formula but a different structural formula - each has different chemical and physical properties

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alkenes

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aliphatic, CnH2n, 1 double bond, unsaturated

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alkynes

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aliphatic, C2H2n-2, triple bond, unsaturated

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example of an alicyclic

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a compound that is aliphatic and cyclic. Cyclopentane

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a heterocyclic structure is

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contains elements other than carbon in the ring structure

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aromatic hydrocarbons are

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have a 6 carbon atom ring with alternating carbon-carbon double bonds - C6H6 - resonance structure with alternating double bond locations

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example of an aromatic hydrocarbons

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benzene

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benzene derivative used in anesthesia

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phenol (found in propofol), aniline (used in amide local anesthetics), benzoic acid (found in ester local anesthetics)

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define functional group

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an atom or group of atoms that is attached to a hydrocarbon chain and that confers some distinctive chemical and physical properties on the organic compound.

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alkane functional group

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CC

CH3CH2CH3 - propane

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alkene functional group

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C(db)C

CH3CH(db)CH2 - propene

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alkyne functional group

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C(tb)C

CH3C(tb)CH - propyne

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alcohol functional group

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OH

CH3OH - Methanol

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ether functional group

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-O-

CH3CH2OCH2CH3 - ethyl ether

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aldehyde functional group

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C(db)OH

CH3CHO - ethanal

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ketone functional group

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C(db)O

CH3C(db)OCH3 - acetone

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acid functional group

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C(db)OOH

CH3C(db)OH - acetic acid

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amine functional group

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NH2

CH3NH2 - methylamine

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amide

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C(db)ONH2

CH3C(db)ONH2 - acetamide

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ester

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C(db)OO

CH3C(db)OOCH2CH3 - ethyl acetate

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making bonds

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releases energy

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alkyl halides

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contain an alkyl group attached to a halogen atom (halothane)

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aryl halides

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have a halogen atom directly attached to an aromatic ring

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alcohol structure

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R-O-H - an aliphatic hydrocarbon in which a hydroxyl group replaces a hydrogen

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alcohol properties

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nonionized, nonelectrolyte, not bases, polar, hydrogen bonding, high boiling points

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3 types of alcohols

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primary, secondary, tertiary

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primary alcohols

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OH attached to a carbon on the end

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secondary alcohols

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OH attached to a carbon with two other carbons attached to it

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tertiary alcohol

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OH attached to a carbon that has three other carbon atoms attached to it

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glycerol is

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trihydric alcohol (3 carbons, 3 OH)
used in soap and nitroglycerin

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two alcohols dehydrate to yield

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an ether (temp 140)

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an alcohol and a dehydrating agent yield

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an alkene (temp 150)

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example of a dehydrating agent is

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H2SO4

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dehydration means

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take out a water

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oxidation reactions

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add an oxygen or take away a hydrogen

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alcohol is oxidized to form

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aldehydes and then acids

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thiol means

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sulfur

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thiols are

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sulfur analogs of alcohols - there's an SH instead of an OH

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disulfide bonds are in

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hair and DNA helix

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thiols are made by

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heating alkyl halides with NaHS

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oxidizing thiols makes

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a disulfide

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ethers are formed

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during dehydration of alcohol

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properties of ethers

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low boiling points, do not form hydrogen bonds, good solvents (do not react with solute), flammable

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diethyl ether is

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the ether traditionally thought of when involved with anesthesia - caused lots of PONV in the old days

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ethers used in anesthesia

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enflurane, isoflurane, desflurane, seveflurane

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side effect of inhaled ether anesthetics

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free F- ion when metabolized hurts kidneys

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aldehydes are made by

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oxidation of a primary alcohol - take out a water by adding an O

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medically relevant aldehydes

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formaldehyde, glutaraldehyde, and acetaldehyde

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why are asians less likely to become alcoholics

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they have a mutation that makes ethanol convert to acetaldehyde quickly, and then alot also have a mutation in the acetaldehyde dehydrogenase enzyme that makes them experience more severe hangove symptoms.

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disulfiram is

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antabuse

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antabuse works by

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preventing oxidation of acetaldehyde to acetic acid - increases the unpleasant side effects of drinking.

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glutaraldehyde is used as

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Cidex - sterilizing agent - effective against spores and viruses

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Formaldehyde

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hardens proteins making insoluble in water, carcinogenic, preserves specimens, enbalming fluids

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aldehydes oxidize to form

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acids

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aldehydes reduce to form

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alcohols

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ketones are made by

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oxidizing a secondary alcohol

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what is responsible for DKA

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acetone (propanone)

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ketone bodies consist of

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ketoacid (acetoacetic acid), ketone (acetone) and beta hydroxybutyric acid

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ketone reactivity

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normally unreactive, cannot oxidize, can be reduced by secondary alcohol that they came from

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carboxylic acids (organic acids) are formed by

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oxidation of aldehydes (2 steps), or oxidizing of primary alcohols are 1 step

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carboxylic acids undergo what reactions

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neutralization reaction (reacts with a base to from salt and water)

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carboxylic acid and alcohol yield

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an ester (succynlcholine is an ester)

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medically important carboxylic acids

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formic acid - bee stings
acetic acid - vinegar
citric acid - citrus fruits
lactic acid - both an acid and an alcohol
pyruvic acid - reduced to lactic acid, changed to acetyl coA for the Kreb's cycle

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esters are formed by

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combining a carboxylic acid and an alcohol

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esters undergo

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hydrolysis to form carboxylic acids

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medically important esters

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local anesthetics (procaine, tetracaine, cocaine, benzocaine), esmolol, remifentanyl, neuromuscular blockers (succinylcholine, atracurium, mivacuriu, cisAtracurium

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2 ester groups on end of succs give it

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a positive charge, making it difficult to cross membranes

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phosphate esters are made by

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adding phosphoric acid to an alcohol

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medically important phosphate esters

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ATP, ADP, AMP, cAMP
DNA, RNA
Phospholipids in tissue cell membranes

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amines are

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organic compounds derived from ammonia

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3 classes of amines are

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primary, secondary, tertiary (referring to the number of H that have been replaced by alkyl goups)

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describe reactions of amines

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basic compounds so add an acid and get a salt, ammonium salts are often a hydrochloride

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another name for ammonium salts

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hydrochloride after the name of the amine

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hydrochlorides are used instead of the amines because

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they are more water soluble

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quaternary ammoniums are

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positively charged - NH4+

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amino acids are

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organic acids + amine group
COOH is acid, NH2 is base therefore will react with either acids or bases

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amphoteric means

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react with either acids or bases

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amides are made by

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organic acid + ammonia (amine)

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amide property

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weakly basic

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an amino acid + an amino acid yields

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a peptide

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medically important amides

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local anesthetics - lidocaine, prilocaine, bupivacaine, ropivacaine, etidocaine, mepivacaine

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benzene facts and aka

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C6H6 - unsaturated - every other double bond in the ring - aka aromatic ring

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benzene properties

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colorless liquid, gasoline-like odor, toxic, skin contact is harmful, inhalation decreased RBC and WBC, mildly carcinogenic, banned as a consumer ingredient

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usual reaction for benzene

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substitution reaction (rarely addition reactions)

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ortho substitution

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two adjacent carbons on the benzene ring have a functional group added

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meta substitution

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there is one carbon between the two carbons on the benzene ring that have a functional group added

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para substitution

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the carbons on the benzene ring that have a functional group added are on opposite side of the ring

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lipophilic part of local anesthetics is derived from

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either benzoic acid or aniline

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medically important benzene derivatives

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TNT, PABA, aniline, ASA, acetaminophen, phenanthrene, phenol, nitrobenzene, benzoic acid, and toluene -

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toluene in the presence of oxygen will become

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benzoic acid

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active ingredient in sunscreen is

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PABA (can cause anaphylaxic reaction)

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isomers are

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molecules with the same chemical formula, and often the same chemical bonds, but in which the atoms are arranged differently - many isomers share similar if not identical properties

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types of isomers

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structural, functional, geometric

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structural isomers have

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same molecular formula and functional groups, but different structural formulas

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functional isomers have

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same molecular formula but different functional groups

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geometric isomers have

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same molecular formula but different structural formula because a double bond or ring systems prevents rotation to change into other form (cis vs trans)

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cis means

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same sided functional groups

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trans means

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opposite sided functional groups

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example of two geometric isomers

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cisatracurium and atracurium

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a chiral carbon is

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a carbon bonded to 4 different groups that is not superimposable on its mirror image, is optically active

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enantiomers are

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two mirror image molecules that cannot be superimposed

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a molecule will have an enantiomer if it

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contains a chiral carbon

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optical isomers have

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same molecular formula, structures are mirror images of one another so they rotate the plane of polarized light equally but in opposite direction

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levo means

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left

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dextro means

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right

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racemic mixture means

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having both left and right rotating light isomers (levo and dextro)

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barbituric acid is made from

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urea and malonic acid (board question)

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examples of barbiturates or sedative-hypnotics

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phenobarbital, pentobarbital, secobarbital, methohexital (brevital) thiopental (sodium pentothal), thiamylal

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naturally occurring opiates

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morphine, codeine, thebaine

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all opiates share a

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phenanthrene structure (3 attached benzene rings

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neuromuscular blockers have

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quaternary ammoniums lending a + charge so drugs won't cross membrane keeping distribution just intravascularly.

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examples of neuromuscular blockers

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acetylcholine, succinylcholine, decamethonum, vecuronium, mivacurium, atracurium, pancuronium, etc.

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know whether local anesthetics are the amide version or the ester version

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examples - procaine, cocaine, ropivacaine, lidocaine, chloroprocaine, tetracaine, prilocaine, etidocaine, bupivacaine (aniline vs benzoic acid)

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steroid base is a

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3 6 carbon ring with a penta ring attacged

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non-barbiturate induction agents are

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ketamine (PCP), etomidate, propofol

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OH is

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always 1 when counting groups for naming

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imidazole is

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a penta ring with 2 nitrogens

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imidazole is formed from

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glyoxal and formaldehyde

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benzodiazepines characteristic

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(versed) - ring structure opens or closes depending on pH.

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pH under 4 makes versed

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water soluble and the ring structure remains open

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pH over 4 makes versed

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lipid soluble and the ring structure closes

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why are iv doses of versed different than po doses

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in the blood pH is 7.4 therefore versed is lipid soluble and crosses into cells easily. If take po, pH is less than 4 so versed becomes water soluble and it takes a much higher dose to get into the cells

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catecholamines are

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sympathomimetics - beta phenylethylamine, epinephrine, norepinephrine, dopamine, isoproterenol, dobutamine