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149 Cards in this Set
- Front
- Back
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
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