Ch. 9- Organic Chemistry Flashcards
organic chemistry
the study of the compounds of carbon
properties of organic compounds
- generally form covalent bonds
- have lower melting/boiling points
- may exist as gases, liquids, or solids at room temp.
- are not generally soluble in water
- do not conduct electricity well
- slower reactions
- almost always undergo combustion
properties of inorganic compounds
- often form ionic bonds
- have higher melting/boiling points
- usually solids at room temp.
- many are polar
- dissolve readily in water
- good conductors of electricity
- react very quickly
- generally do not burn
hydrocarbon
an organic compound that contains only carbon & hydrogen
aliphatic compound
a nonaromatic substance, which has little or no multiple bonding between carbon atoms
alkane
hydrocarbons with only single bonds; a saturated hydrocarbon
structural formula
a chemical formula that shows how the atoms of a molecule are arranged, to which other atom(s) they are bonded, and the kinds of bonds
saturated hydrocarbon
an alkane; a compound of carbon and hydrogen with only single bonds
why are alkanes considered “saturated hydrocarbons”?
because each carbon atom is “saturated” with hydrogen atoms; that is, each carbon is bonded to the maximum number of hydrogen atoms
general formula that represents alkanes
CnH2n+2
condensed structural formula
a chemical formula for an organic compound that omits the bonds joining hydrogens to carbons
homologous series
a series of compounds whose adjacent members differ by a fixed unit of structure
isomers (constitutional isomers)
compounds that have the same molecular formula, but different structures
properties of alkanes
- most are flammable
- at room temp…
- alkanes with 1-4 carbon atoms per molecule= gases
- alkanes with 5-16 carbon atoms per molecule= liquids
- alkanes with 16+ carbon atoms per molecule= solids
- densities of liquid & solid alkanes are typically less than that of water
- nonpolar
- insoluble in water
- float on top of water
- they dissolve other organic substances of low polarity
- undergo few chemical reactions, most important chemical property is undergoing combustion, producing heat
- mainly serve as fuels
- burn with a clean yellow flame
how does methane effect the human body?
- methane barely reacts with the human body
- humans could breathe a mix of 80% methane & 20% oxygen, even though its highly flammable
- humans would die from breathing in 100% methane, but not because of its presence, but because of lack of oxygen
how do light liquid alkanes effect the body?
- light liquid alkanes will dissolve & wash away body oils when in contact with skin
- repeated contact causes dermatitis
can we ingest alkanes?
NO
- ingestion of most alkanes causes serious damage to lungs and/or other internal tissues
- alkanes cause chemical pneumonia by dissolving fatlike molecules from cell membranes in alveoli, allowing lungs to fill with fluid
what’s one exception to ingesting alkanes?
mineral oil, which is safe to ingest to use as a laxative
how do heavier liquid alkanes effect the body?
they’re used as skin softeners (example, petroleum jelly)
meth-
one (for naming alkanes)
eth-
two (for naming alkanes)
prop-
three (for naming alkanes)
but-
four (for naming alkanes)
pent-
five (for naming alkanes)
hex-
six (for naming alkanes)
hept-
seven (for naming alkanes)
oct-
eight (for naming alkanes)
non-
nine (for naming alkanes)
dec-
ten (for naming alkanes)
cyclic hydrocarbon
a hydrocarbon in which the carbon chain joins to itself in a ring
whats the simplest possible cyclic hydrocarbon?
cyclopropane (C3H6)
cycloalkanes
cyclic hydrocarbons containing only single bonds
general formula that represents cycloalkanes
CnH2n
skeletal structure
representation of the carbon skeleton of a molecule, often shown as a geometric figure or shape
whats the simplest hydrocarbon molecule possible?
CH4 (methane)
whats the simplest alkene possible?
C2H4 (ethylene)
alkene
a hydrocarbon containing one or more double bonds
general formula that represents alkenes
CnH2n
most important organic chemical produced commercially
ethylene (C2H4)
alkyne
a hydrocarbon containing one or more triple bonds
general formula that represents alkynes
CnH2n-2
simplest member of the alkyne family
acetylene (C2H2)
unsaturated hydrocarbon
an alkene, alkyne, or aromatic hydrocarbon; a hydrocarbon containing one or more double or triple bonds or aromatic rings
what does the “1” indicate in “1-pentene”?
the location of the double bond (1 means the double connects the first carbon atom to the next)
what does the “1” indicate in “1-pentene”?
the location of the double bond (1 means the double connects the first carbon atom to the next)
addition reaction
a reaction in which the single product contains all the atoms of two reactant molecules
properties of alkenes & alkynes
- generally, hydrocarbons at room temp…
- with 2-4 carbon atoms per molecule= gases
- with 5-18 carbon atoms per molecule= liquids
- with 18+ carbon atoms per molecules= solids
- insoluble in water
- float on top of water
- combustable
- undergo many more chemical reactions than alkanes including addition reactions (a reaction in which the single product contains all the atoms of two reactant molecules)
- burn with a smokey flame
- they can add to each other to form large molecules called polymers
geometric isomers
molecules having the same molecular formula that are locked into their spatial positions with respect to one another due to a double bond or a ring structure
requirements for geometric isomerism
- rotation must be restricted in the molecule
- there must be two different groups on each of the doubly bonded carbon atoms
aromatic compound
a strong-smelling compound that has a ring structure and properties like those of benzene
who discovered benzene?
Michael Faraday
August Kekulé
prepared a structure for benzene that contained double bonds
why is benzene so stable?
its carbon atoms conform to the octet rule due to its constantly moving ring of electrons, which resist being disrupted
why has the use of benzene been restricted?
long exposure to benzene causes leukemia
name some simple aromatic hydrocarbons & their uses
- benzene, toluene, xylenes
- liquids that float on water
- used as solvents, fuels, and to make other benzene derivatives
- naphthalene
- volatile, white, crystalline solid
- used as an insecticide, especially moth repellant
substituent
an atom or group of atoms substituted for a hydrogen atom on a hydrocarbon
what does the “1, 4” indicate in “1,4-C6H4(CH3)2”
the relative location(s) of the substituent
similar properties of chlorinated hydrocarbons
- only slightly polar
- do not dissolve in water (which is highly polar)
- dissolve & dissolve in fats, oils, greases, and other substances of low polarity
chlorofluorocarbons (CFCs)
compounds containing carbon AND BOTH fluorine & chlorine
properties & effects of CFCs
- CFCs don’t dissolve in water and barely react with most other substances
- CFCs are used as propellants, but are being phased out due to their ability to deplete the ozone layer
what does “per-“ indicate in “perfluorocarbon”
“per-“ = replaced
so we know that this is a hydrocarbon with all of its hydrogen atoms replaced by fluorine (-fluoro-) atoms
alkyl group (–R)
the group of atoms that results when a hydrogen atom is removed from an alkane
functional group
an atom or group of atoms that confers characteristic properties to a family of organic compounds
functional group
an atom or group of atoms that confers characteristic properties to a family of organic compounds
write names and formulas of simple alkyl groups in 9.5!!!!!
methyl
ethyl
propyl
and so on….
why are functional groups important?
they dictate the type of chemical reaction a compound will undergo
alcohol (ROH)
an organic compound composed of an alkyl group and a hydroxyl group
what are the common alcohols & which one is the simplest?
- methyl alcohol (simplest)
- ethyl alcohol
- propyl alcohol
- isopropyl alcohol
what is methanol made from?
wood
what is ethanol made from?
- fermentation of grain or other starchy/sugary materials (auto fuel & beverages)
- mixing ethylene & water (industrial uses)
whats the most abused drug in the US?
ethanol
how is methanol toxic?
- it oxidizes in the body to form formaldehyde
- ingesting just 1 oz can cause blindness and/or death
how is ethanol toxic?
- it slows physical & mental abilities
- in small amounts, this makes people feel “drunk”
- in larger amounts, this causes unconsciousness and/or death
explain the toxicity of isopropanol
its more toxic than ethanol, but less toxic than methanol; causes illness and sometimes death
what do ethylene glycol, propylene glycol, and glycerol have in common?
they’re all alcohols that contain more than one hydroxyl group (OH)
ethylene glycol use & effect on the body
- main ingredient in permanent antifreeze
- oxidizes in the liver to form oxalic acid, which can damage the kidneys, leading to death
propylene glycol use & effect on the body
- safer ingredient in permanent antifreeze
- not toxic
glycerol uses & effect on the body
- by-product from fats during soap manufacturing
- used in lotions to keep skin soft & in food additives to keep cakes moist
- reacts with nitric acid to make an important vasodilator
phenols
a compound with an -OH group attached to a benzene ring
what was the first antiseptic ever used, by who, and why is it not ideal?
Joseph Lister used phenol; not ideal because it kills healthy cells
how do we use phenols today?
as a disinfectant or as an antioxidant
ether (ROR’)
a molecule with two hydrocarbon groups attached to the same oxygen atom
diethyl ether
- best-known ether that used to be the most popular anesthetic, but not anymore due to its side-effects
- dissolves many organic compounds that are insoluble in water
- readily evaporates
- has little chemical reactivity other than being highly flammable
explain how ethers react with oxygen
they react slowly with oxygen to form unstable peroxides, which can decompose explosively
which ether is produced the most commercially and what do we use it for?
- make ethylene glycol
- sterilizes medical instruments
- used in the synthesis of detergents
what do we use ethylene glycol for?
antifreeze and polyester fibers
thiol (R–SH)
an organic compound composed of an alkyl group and a thiol (–SH) group
carbonyl group (C=O)
a functional group consisting of a carbon atom joined to an oxygen atom by a double bond
aldehyde (RCHO)
an organic compound with a carbonyl group that has a hydrogen atom attached to the carbonyl carbon
ketone (RCOR’)
an organic compound with a carbonyl group between two carbon atoms
ketone (RCOR’)
an organic compound with a carbonyl group between two carbon atoms
what is the simplest aldehyde? name some of its properties, how its used, and how its created
formaldehyde (HCHO)
- gas at room temp & readily soluble in water
- used as a preservative for bio specimens, in embalming fluid, making plastics, & in disinfectants
- created by the oxidation of methanol
what are the 4 common aldehydes?
- formaldehyde
- acetaldehyde
- propionaldehyde
- butyraldehyde
what is benzaldehyde
an aldehyde attached to a benzene ring
what is the simplest ketone? how is it created and used?
acetone
- made by the oxidation of isopropyl alcohol
- commonly used as a solvent for certain organic materials, also used as paint/varnish removers
name the common ketones
- acetone
- ethyl methyl ketone
- isobutyl methyl ketone
how can we best distinguish ketones from aldehydes?
ketones have the carbonyl INSIDE its carbon chain, whereas aldehydes have the carbonyl ON THE END of its carbon chain
carboxyl group (–COOH)
a carbon atom with a double bond to one oxygen atom and a single bond to a second oxygen atom, which in turn is bonded to a hydrogen atom; the functional group of carboxylic acids
carboxylic acid (RCOOH)
a foul-smelling organic compound that contains the carboxyl functional group
what is the simplest carboxylic acid and how is it produced?
formic acid; poisonous weak acid injected by ant bites & wasp/bee stings
what is the most familiar carboxylic acid?
acetic acid, also known as vinegar
what’s the most foul-smelling compound and where is it found?
butyric acid; its an ingredient in body odor, which helps dogs find people
benzoic acid
the acid with a carboxylic group attached directly to a benzene ring
name the simple carboxylic acids
- formic acid
- acetic acid
- propionic acid
- butyric acid
- benzoic acid
ester (RCOOR’)
a fruity tasting & smelling organic compound derived from a carboxylic acid and an alcohol
amino group (–NH2)
a functional group comprised of a nitrogen atom bonded to two hydrogen atoms
amine
a nitrogen compound derived from ammonia by replacing one or more hydrogen atoms with alkyl or aromatic group(s)
amide group (–CON–)
a functional group in which a carbon is joined to an oxygen atom by a double bond and to a nitrogen atom by a single bond
heterocyclic compound
a cyclic compound in which one or more atoms in the ring are not carbon
alkaloids
(usually heterocyclic) amines that occur naturally in plants
