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124 Cards in this Set
- Front
- Back
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Characteristics of Organic Molecules
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- all contain carbon atom
- may contain hydrogen, nitrogen, oxygen, and halogens - form covalent bonds or polar covalent bonds - able to support combustion - nearly all drugs are organic molecules |
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functional group
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the group of atoms that determines the characteristic properties of a compound
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3 parts of IUPAC naming (nomenclature)
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1. prefix: dependent on the substituent
2. parent: portion of the name which is defined by the number of carbons in the longest chain 3. suffix: where the family name comes from |
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nomenclature of 1 carbon
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meth-
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nomenclature of 2 carbons
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eth-
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nomenclature of 3 carbons
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prop-
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nomenclature of 4 carbons
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but-
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nomenclature of 5 carbons
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pent-
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nomenclature of 6 carbons
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hex-
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nomenclature of 7 carbons
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hept-
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nomenclature of 8 carbons
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oct-
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nomenclature of 9 carbons
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non-
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nomenclature of 10 carbons
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dec-
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Hydrocarbons
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an organic compound that contains only carbon and hydrogen.
- only in single bonds |
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properties of Alkanes
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- Non-polar
- insoluble in water - soluble in non-polar organic solvents - less dense that water - low molecular weight - low boiling point - Flammable - not very reactive |
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When naming Alkanes start numbering where?
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start numbering at the end of the chain closest to the first substituent
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Alkane
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- contains only C-H and C-C single bonds
- end in -ane |
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Alkenes
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- contain C=C double bonds
- end in -ene |
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Alkyne
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- contain C triple bond C
- end in -yne |
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Aromatic
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- contain a six-membered ring of carbon atoms with three alternating double bonds
- ring shaped |
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Alykylhalide
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- contain a carbon-halogen bond
(halogen = F, Br, Cl, I) |
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Alcohol
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- have a carbon-oxygen bond
- C-O-H - end in -ol |
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Ether
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- have 2 carbons bonded to the same oxygen
- C-O-C |
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Amine
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- have a carbon-nitrogen bond
- C-N (nitrogen can then bond to 2 other things) - end in -amine |
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Aldehyde
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- contain a carbon=oxygen double bond and where the carbon double bond to oxygen is bonded to hydrogen
- end in -al - C-H (and the double bond O above C) |
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Ketone
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- have a carbon=oxygen double bond
- the C-C(double bond O)-C - end in -one |
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Carboxylic acid
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- have a carbon=oxygen double bond and and -OH at the end
- end in -ic acid |
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Anhydride
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- have two carbon=oxygen double bonds and a single bond oxygen between two carbons
- C (double bond O)-O-C (double bond O) |
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Ester
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- have carbon=oxygen double bond with C-O-C at the end
- end in -ate |
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Amide
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- have a carbon=oxygen double bond with an amine at the end.
- C-C (double bond oxygen)-NH2 |
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functional group
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group that determines the family
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Substituent group
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an atom or atoms attached to a parent compound
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Cycloalkanes
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- simplest cycloalkane is cyclopropane
- 3-carbon ring - each carbon still makes 4 covalent bonds but 2 of the bonds are to the next carbon and 2 to hydrogen - number should start at the group that has alphabetic priority and then proceed around the ring so that a second group has the lowest number possible |
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2 Alkane reaction
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1. Combustion
2. Halogenation |
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combustion
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the products are carbon dioxide and water or carbon monoxide if the amount of oxygen is insufficient
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halogenation
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alkanes react with halogen forming a hydrogen halide and a halogenated alkane
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Halothane
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the only alkane in current use as an anesthetic
Halogenated alkane named halothane b/c only one H left and the rest of the bonds with C are with halothane group elements |
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Are alkenes said to be saturated or partially saturated (unsaturated)
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partially saturated (unsaturated) b/c there are double bonds present.
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Saturation
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a saturated molecule is one in which each carbon is bonded to the maximum number of hydrogens
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Isomers
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compounds with the same molecular formula but different structures
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2 classifications of Isomers
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1. Structural (constitutional) isomers
2. Stereoisomers |
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Structural Isomers
(constitutional) |
same molecular formula but differenct connections (bonding) among individual atoms
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Stereoisomers
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identical formulas and connections but different arrangements of atoms in 3-dimensional space
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3 types of Stereoisomers
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1. Optical Isomers
2. Geometric Isomers 3. Comformational isomers |
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Optical Isomers
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- not superimposable on eachother
- rotation of plane polarized light either clockwise (+) or counterclockwise (-) |
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Clockwise rotation known as
(rotate to the right) |
Dextrorotatry
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Counterclockwise rotation known as
(rotate to the left) |
Levorotatory
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Geometric Isomers
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Cis-trans isomers
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Enantiomers
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optial isomers
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Cis
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in cis-configurations, the groups are on the same side of the double bond
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trans
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in trans-configurations, groups attach on the opposite sides of the double bond
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Stereoselectivity
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the RELATIVE difference between enantiomers
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Stereospecificity
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the ABSOLUTE difference between enantiomers
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Enantiomers
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can antagonize the effects of one another
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anesthetics supplied as RACEMIC mixtures of OPTICAL ISOMERS
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1. Ketamine
2. Thiopental 3. Volatiles except seyoflurane which is achiral |
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anesthetics available as a SINGLE ENANTIOMER of a recemic mixture
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Etomidate
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Anesthetics that are STRUCTURAL ISOMERS
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1. Isoflurane
2. Enflurane |
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Anesthetics exhibiting GEOMETRIC, CIS-TRANS ISOMERISM
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Cis-atracurium (Nimbex)
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5 Types of Alkene Reactions
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1. Chemically reactive at double bond
2. Additions 3. Eliminations 4. Substitutions 5. Rearrangements |
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4 Alkene Addition Reaction
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1. Hydrogenation
2. Halogenation 3. Hydhalogenation 4. Hydration |
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Hydrogenation
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- addition of hydrogen
- saturation of fats and oils |
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Halogenation
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- addition of a halogen
- result is an alkyl haide |
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Hydrohalogenation
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- addition of HX where X is a halogen
- result is an alkyl haide - Markovnikov's rule applies |
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Markovnikov's Rule
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states that the hydrogen goes to the carbon already bonded to the most hydrogens & the halogen goes to the other carbon
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Hydration
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- addition of water
- Markovnikov's rule applies here |
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Polymer
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a large molecule formed by the repetitive bonding together of many smaller molecules
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Monomer
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a small molecule that is used to prepare a polymer
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Polymerization reaction
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occur when monomer is treated with a catalyst at the C=C double bond
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Aromatic Compound Properties
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- nonpolar
- insoluble in water - Volatile - Flammable - Toxic- carcinogenic - Propofol contains a substituted benzene ring |
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Prefixes of Benzene Ring
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- benzene rings have different prefixes depending on where the substituent group lands on the ring:
"ortho" (1,2) "meta" (1,3) "para" (1,4) |
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Phenyl Group
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- functional group when the benzene ring is the substituent
- C6H5 |
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Similarity between Alcohols, Phenols, and Ethers
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all organic relatives of water where 1 or both hydrogens has been replaced by an organic substituent
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Characteristics of Alcohols and Phenols
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- organic compounds bonded to an -OH group
- -OH group is called "hydroxyl group" - basic formula for an alcohol is R-OH where R = any organic group - Basic formula for phenol is Ar-OH (Ar is a benzene ring) |
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Characteristics of Ether
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- oxygen atom bonded to 2 organic groups
- basic formula is R-O-R |
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Alcohols
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a compound that has a hydroxyl group bonded to a saturated, alkane-like carbon atom
ex: Methyl alcohol, ethyl alcohol, isopropyl alcohol, ethylene glycol, and glycerol |
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Classes of Alcohols
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1. Primary
2. Secondary 3. Tertiary |
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Primary Alcohols
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2 hydrogen and 1 organic substituent group attached to a Carbon (along with the -OH)
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Secondary Alcohols
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2 organic groups and 1 hydrogen (and 1 -OH) attached to a carbon
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Tertiary Alcohol
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Only organic groups attached to the Carbon.
does have the -OH group attach to the carbon. |
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Properties of Alcohols
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- more polar that hydrocarbons causing hydrogen bonding b/c of the -OH group
- solubility in water depends on the # of carbons (organic components) associated with the -OH group - the more carbons, the less water soluble - with fewer carbons, the influence of the -OH group is greater in terms of solubility |
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Reactions of Alcohols
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1. Dehydration
2. Oxidation |
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Dehydration
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- reverse of hydration of an alkene
- result of dehydration of an alcohol is an alkene |
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Oxidation
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- increases the number of carbon-oxygen bonds
- decreases the number of carbon-hydrogen bonds - oxidation of an alcohol results in a carbonyl compound (aldehyde or ketones) - increase the number of Carbon-Oxygen bonds and decreases the number of Carbon-Hydrogen bonds |
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Primary alcohol oxidizes
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results in an aldehyde + water
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Secondary alcohol oxidizes
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results in a ketone + water
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Tertiary alcohol oxidizes
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does not react with oxidizing agents b/c no hydrogen available to attach to the -OH group to form water
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2 steps in alcohol oxidation
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1. make into an aldehyde and water (ethanol is a primary alcohol)
2. make into an acetic acid (carboxylic acid) |
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Acute ingestion and anesthesia
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acute intoxication decreases anesthetic requirements
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Chronic use/abuse of anesthesia
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induces the cytochrome P-450 system and increases anesthetic requirements due to accelerated metabolism
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Phenols
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compounds that have an -OH group bonded directly to an aromatic, benzine-like ring
- topical anesthetic - toxic |
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Joseph Lister
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in 1867
demonstrated the use of phenol as an antiseptic (disrupts the cell walls of microorganisms) |
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Ether as an Anesthetic
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- discovered in 1840s
- Quick acting - very effective - long recovery time - pungent; unpleasant induction - Hi incidence of nausea and vomiting - Highly flammable liquid; vapor forms explosive mixtures with air |
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What are Ethers?
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- compounds with 2 organic groups bonded to the same oxygen atom
- named by naming the 2 organic groups and adding "ether" |
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Alkoxyl group
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is an ether as a substituent
- R-O- - CH3O- is the methoxy group (a substituent on methyoxyflurane) |
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The only Non-Ether Volatile Anesthetic
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Halothane
- it's an Alkane |
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Alkyl Halide
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- halogen containing compound
- alkyl group bonded to a halogen atom R-X |
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Naming Halogen containing compounds
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halogen name is added as a prefix to the name of the parent alkane
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What is Ethyl chloride?
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a topical anesthetic that cools the skin via rapid evaportaion
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What is Chloroform
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a general anesthetic
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What are Amines?
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- derivative of ammonia
- organic group (1) bonded to nitrogen |
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Quaternary ammonium
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the lone pair in Nitrogen permits 4th group to bond to the nitrogen and if this occurs the product is a quaternary ammonium compound and it has a positive charge (cation) which can then form an ionic bond with an anion
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3 Types of Amine bonds
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1. Primary
2. Secondary 3. Teritary |
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primary Amine bond
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Nitrogen with 2 hydrogen and 1 R group
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Secondary Amine bond
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Nitrogen with 1 Hydrogen and 2 R groups
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Tertiary Amine bond
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Nitrogen with No Hydrogen, only R groups bonded to it
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Properties of Amines
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- weak bases
- form hydrogen bonds b/c of lone pair - boiling point is higher than alkanes (b/c of hydrogen bonding) but lower than alcohols - volatile amines (strong odor) - many are physiologically active (neurotransmitters) - simpler amines are water-soluble b/ of hydrogen bonding - toxic by ingestion |
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action of a base
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bases accept a hydrogen ion from an acid
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Neurotransmitters
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- most neurotransmitters are amines
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examples of neurotransmitters
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- Acetylcholine: a quaternary ammonium compound
- Anticholinergic medications: prevent the effects of Ach on end-organs and are either tertiary (atropine) or quaternary (glycopyrollate) - Atropine crosses the BBB but glycopyrollate doesn't |
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Carboxylic Acid and Derivative
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carboxylic acid = organic acid
and acid donates a hydrogen ion only the hydrogen attached to the oxygen can be donated ex: acetic acid |
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Naming Carboxylic Acids
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- end in -oic acid
- common names: identifying carbon atoms next to -COOH - acyl group remaining when carboxylic acid looses -OH is named by replacing "-ic" at the end of the acid name with "-oyl" exception is acetic acid/acetyl group |
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Reactions of Carboxylic Acids
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1. Eserification
2. Amide formation 3. Substituted amides |
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4 Anesthetics that are Esters
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1. Procaine
2. Cholorprocaine 3. Tetracaine 4. Cocaine |
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5 Anesthetics that are Amides
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1. Lidocaine
2. Mepivacaine 3. Bupivacaine 4. Etidocaine 5. Prilocaine |
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3 Alkane Anesthetics
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1. Halothane
2. Cycloprpane 3. Chloroform |
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Alcohol Anesthetic
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Propofol
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3 Amine Anesthetics
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1. Dopamine
2. Atropine (anticholinergic) 3. Glycopyrilate (anticholinergic) |
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4 Ether Anesthetics
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1. Diethyl ether
2. Enflurane 3. Desflurane 4. Isoflurane |
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2 Alkyl Halide Anesthetics
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1. Chloroform
2. Halothane |
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reaction of esters
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can cause allergic reaction
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some drugs metabolize by ester hydrolysis resulting in:
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resulting in a carboxylic acid and an alcohol
ex: Remifentynol and Atricurium |
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3 examples of Alkyl Halide (Halogenated Alkane)
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1. Ethyl Chloride
2. Choloroform 3. Halothane |
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Name a Tertiary amine and properties
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Atropine
- it will cross the BBB |
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Name a Quaternary amine and properties
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Glycopyrollate
- it has a positive charge and therefore will not cross the BBB |
