MCAT Organic Chemistry
Alkane, Alkene, Alkyne and reactions
Terms in this set (101)
Chain of carbons connected by single bonds with hydrogen atoms attached.
Use the Greek root for the number of carbons followed by the ending, -ane
di, tri, t, sec, n-
iso, neo, cyclo
contain carbon carbon double bonds. Use same root of alkane but end with "ene"
propylenes attached to a backbone at the C-3 position. Meaning the double bond at end of the chain and single bonded carbon at rest
refers to the =CH2 group
carbon carbon triple bonds. Suffix-yne.
Common name for ethyne
y = position of double bond, x is position of triple bond, root is the prefix representing the length of the principal carbon chain
compounds with halogen
F, CL, Br, I
two hydroxyl groups
diols with hydroxyl group on adjacent carbon
diol with hydroxyl group on same carbon
functionality is specified by alkoxy-prefix. ROR
carbon double bonded to an oxygen
carbonyl located at the end of the chain named by replacing al with e. e.g. butanal
name for mathanal
name for ethanal
name for propanal
carbonyl located in middle or somewhere in chane. Named with ONE
always receive number one. contain carbonyl and OH group, very oxidized. highest priority functional group.
nitrogen containing compound, longest chain attached to nitrogen used in backbone. use e and replace with AMINE. if more complex molecule present, use prefix amino. IF additional group added, use N-
share molecular formula but have different chemical and physical properties
same molecular formula but different structure
same chemical formula. same atomic connectivity . different in how atoms are arranged in space
differ in position of substitutents attached to a double bond or cycloalkane. Cis or trans or e or z
object that is not superimposable upon mirror image
carbon with four different substituents and lack a plane of symmetry
nonsuperimposable mirror image of chiral objects, a specific steroisomer.
three different substitutents often have plane of symmetry. and rotation of 180 will allow molecule to be superimposed on mirror image
spatial arrangement of the atoms or groups of a sterioisomer
configuration in relation to another chiral molecule. use it to determine if a molecule is an enantiomer, diastereomer, etc
describes the exact spatial arrangement of groups of atoms independent of other molecules.
lowest priority group projects into the page
moleculse that have the opposite configuration at their one chiral center. or if multiple chiral centers, must have the opposite configuration at every one of their chiral centers to be enantiomers. identical physical properties and much of the same chemical properties. but differe in optical activity and how they react in a chiral environment
if a compound is able to rotate plane polarized light.
a = observed rotation / concentration * length
rotations cancel each other out therefore no optical activity
non mirror image of configurational isomers. cis and trans alkenes are them. possible when a molecule has two or more stereogenic centers that differ at some but not alll of the centers. they require multiple chiral centers.
how many stereoisomers can a molecule have with n chiral centers
a molecule with an internal plane of symmetry
most similar. same molecule only at different points in their rotation. show them with newmans projections
most favorable of staggared conformations
methyl are 60 degrees apart. kinda stable
highest energy no separation. or 120 separation.
arise from angle strain, torsional strian and nonbonded strain
when bond angles deviate from ideal values
results when cyclic molecules must assume conformations that have eclipsed interactions
results when nonadjacent atoms or groups compete for space. dominant source of energy in flagpole interactions of the boat conformation. thus it goes in various conformations like chair boat and twist.
when boat flips
transfer of electrions from one atome to another
sharing of electron between atoms
n, l, ml, ms
when two atomic orbitals combine. obtained mathematically by adding or subtracting wave functions. if sings are the same, make bonding, if different, less stable antibonding.
when a molecular orbital is formed head to head or tail to tail. all single bonds are tehese.
when two p orbitals line up in parallel and electron clouds overlap. it exsits over a single bond.
a sigma bond and two pi bonds
formed by mixing different types of orbitals
one s and three p orbitals
one s and two p 120 degree apart
two p orbital form pi and third p orbital combine with s to make two sp hybrid. 180 degree apart
no double bonds. it has the maximum number of hydrogens.
is bonded to only one other carbon atom
reaction of alkane with oxygen to form carbon dioxide, water and heat.
C3H8 + 5O2 = 3CO2 + 4H2O + heat
combustion reaction occurs through a radical process
in which one or morehydrogen atoms are replaced with a halogen atom. via free radical substitution
initiation propagation termination
steps of free radical substitution
occur when a molecule is broken down by heat. used to reduce the avverage molecular weight of heavy oils. c-c- bonds are cleave dand make small chain alkyl radicals that recombine to form different alkanes
a radical transfers a hydrogen atom to another radical and makes an alkane and alkene
combustion, disproportionation, free-radical substitution, pyrolysis
alphabetical order of alkane rxn
nucleus lover. electron rich species that are attracked to charged atoms
charged, need electrons
more likely it is to attract positively charged proton. nucleophilic strength decreses: RO->HO>RCO2>ROH>H2O
solvents with protons in solution, e.g. water or alcohol. large atoms tend to be better nucleophiles in here because they can shed the solvating protons around them and are more polarizable
what are the best leaving groups?
reducing an alkene by adding molecular hydrogen to double bond with aid of metal catalyst. e.g. pt, pd, ni. takes place on surface of metal so it does syn addition
electrons of pi bond are reactive and easily attacked by molecules that want e pair e.g. electrophiles.
electrophilic addition of HX
e of double bond act as lewis base and react with hydrogen of hx. make carbocation intermediate. use markonikovs rule
goal is to produce most stable carbocation
electrophilic addition of X2
fast process. double bond is nucleophile and attack x2. make cyclic halonium ion with either br or cl. and make dihalo trans
electrophilic addition of H2O
water can be added to alkenes under acidic conditions. make carbocation. ends with alcohol
electrophilic addition of free radicals
in presence of peroxide, oxygen or ultraviolet light. antimarkonikov because they want a stable free radical. therefore X ends up on least subsituted carbon
diborane add to double bond. boron acts as lewis acid and attaches to less hindered carbon. hydride transferred to adjacent carbon. antimarkonikov, alcohol produced
if reagent has a bunch of oxygen
cold potassium permanganate
alkenes oxidzed with kmno4, if made with cold, dilue, make OH on each side of double bond, diols or glycol in syn orientation
hot, acidic potassium permanganate
nonterminal alkenes are cleaved to form two molar equivalent of carvoxylic acid ..make keton
cleaves double bond in half, it only oxidizes the carbon to an aldehyde under reducing conditions. if ozidizing make same product as KMNO4
ozonolysis under hot acidic kmO4, e.g. H2O2 condition
zn/h or CH3/s with ozonolysis
what is produced when o3 with lialh4 or nabh4
alkene oxidized with this, strong oxidizing agent. CH3CO3H or mcpba and it makes epoxide or oxirane
creation of long, high molecular weight polymer composed of repeating subunit called monomers. occur through a radical mechanism.
hydrocarbon with one or more carbon carbon triple bond
palladium or barium sulfate (BaSO4) with quinoline. occur on metal surface, make cis.