Organic Chemistry Flashcards
combination of two or more atomic orbitals to form the same number of hybrid orbitals, each having the same shape and energy
hybridization
effect of increasing bond strength to bond length and %s
decrease, increase
alkane is unsaturated or saturated hydrocarbon
saturated hydrocarbon
the name that we use regularly/commonly
common name
one that follows the IUPAC system for naming a compound
IUPAC name
the 3D structure of a molecule
stereochemistry
a carbon with 4 different atoms or groups attached to it
chiral center (stereogenic)
chiral compounds have
-at least one chiral center
-has no plane of symmetry
optical isomers
enantiomers
pair of stereoisomers that are chiral
enantiomers
have the same physical properties except that they rotate plane-polarized light in opposite directions
enantiomers
isomers wherein the compound differs in connectivity
constitutional isomers
3D spatial arrangement (absolute configuration)
R,S
rotation of plane-polarized light (physical property)
D,L or (+,-)
in __, the prefixes R (latin rectus for right) and S (latin sinister for left) are attached to the IUPAC name
Cahn-Ingold-Prelog
__ are optically active
chiral compounds
if rotation is to the right, the compound is
dextro: d or +
if rotation is to the left, the compound is
levo: I or -
a mixture having equal amounts of two enantiomers
racemic mixture
instrument used to determine the optical rotation; a device used to measure the rotation of plane polarized light caused by optically active compounds in a solution
polarimeter
the overlap of the larger lobes of the sp3 orbitals with the 1s orbitals of hydrogen; head-on overlapping of atomic orbitals
sigma bond
formed when unhybridized p orbitals of carbon overlap
pi bond
combination of the sigma bond and a pi bond extending between the same pair of atoms
double bond
result of the overlap of one sigma bond and two pi bonds
triple bond
an atom or group of atoms that are responsible for the characteristic chemical behavior of organic compounds
functional group
compounds made up of only carbon and hydrogen
hydrocarbons
contain the carbonyl group (C=O) where C is surrounded by three groups, making it sp2 hybridized and trigonal planar
carbonyl compounds
compounds that contain the carboxy group, -COOH; very polar compounds and exhibit H-bonding
carboxylic acids
object or molecule is not superimposable on its mirror image
chiral
main source of alkanes (hydrocarbons)
crude oil
four general types of organic reactions
addition, elimination, substitution, rearrangement
detailed description of how bonds are broken and formed as reactant(s) is(are) converted to product(s)
reaction mechanism
the larger the molecular weight, the __ the boiling point
higher
for the same molecular weight, the larger the surface area, the __ the boiling point
higher
more branching, __ boiling point
lower
a __ is a concerted reaction where a starting material is converted directly to a product
one-step reaction
increase in energy when tetrahedral bond angles deviate from the optimum angle of 109.5 deg
angle strain
an ion or molecule that is electron deficient and would accept a pair of electrons from a nucleophile to form a new covalent bond
electrophile (electron loving)
halogenation reaction of alkanes
initiation > propagation > termination
most important sources of alkanes
natural gas and petroleum
complex mixture of compounds, mostly alkanes and other hydrocarbons with 1-40 carbon atoms
petroleum
contains mostly methane (about 70-90%), with some ethane, propane, butane, and sometimes small amounts of carbon dioxide, nitrogen, hydrogen sulfide or helium
natural gas
distillation of crude petroleum separates it into various fractions
refining
__ of alkanes produces carbon dioxide and water if the amount of oxygen is sufficient (complete combustion).
combustion
produced when the supply of oxygen is insufficient
carbon as soot and carbon monoxide. together with water
results in increase in the number of C-Z bonds (usually C-O bonds) or a decrease in the number of C-H bonds
oxidation
results in a decrease in the number of C-Z bonds (usually C-O bonds) or an increase in the number of C-H bonds
reduction
__ of alkanes occur in the presence of heat or light, converting alkanes to alkyl halides
halogenation
rotation around __ is restricted
C=C
true or false: trans alkenes are more stable than cis alkenes
true
the overlap between a sigma bond and a p-orbital
hyperconjugation
alkenes typically undergo
electrophilic addition
there is only one of two possible orientations of addition that occurs
regiospecific reactions
predicts that H will add to the carbon with fewer alkyl substituents and X will add to the carbon with more alkyl substituents
Markovnikov’s rule
carbocation stability follows the order:
3 degree > 2 degree > 1 degree
a simple chemical test for the presence of pi bonds in unknown compounds
bromination
__ of an alkene breaks both the pi and sigma bonds of the C=C to form two C=O
oxidative cleavage
detailed description of how bonds are broken and formed as reactant(s) is(are) converted to product(s)
reaction mechanism
symmetrical bond breaking (homolysis) generates __, which are uncharged species with unpaired electrons
radicals
electron rich
nucleophile
used to detect position of double bond
ozonolysis
contains a six-membered ring and three additional degrees of unsaturation
benzene
ortho- and para- directing
activating groups
meta- directing
deactivating groups
reaction of benzene where a hydrogen atom is replaced by an electrophile
electrophilic aromatic substitution
capable of dipole-dipole interactions and intermolecular hydrogen bonding
polar protic solvents
exhibit dipole-dipole but have no O-H or N-H so they are incapable of hydrogen bonding
polar aprotic solvents
always product of elimination
alkenes
have higher boiling points than ethers and alkanes
alcohols
elimination of water from alcohols
dehydration
substitution with HCl/ZnCl2, determines if primary, secondary, or tertiary alcohols
lucas test
oxidation with acidic Cr6+
Jones test
product of strong oxidizing agent plus primary alcohol
carboxylic acid
product of oxidation of secondary alcohol
ketone
product of oxidation of tertiary alcohol
no product
how many carbons of alcohol are still soluble with water?
5 carbons below
product of dehydration of alcohols with strong acid
alkene
product of alcohol oxidation with PCC or PDC
aldehyde
alcohol can undergo these reactions:
substitution (alkyl halide), oxidation (aldehyde, carboxylic acid, or ketone), elimination (alkene), deprotonation (alkoxide)
acid in wine
tartaric acid
carboxylic acid undergoes what reaction
nucleophilic acyl substitution
loss of CO2 from carboxyl group when heated to a very high temperature
decarboxylation
prone to decarboxylation
ketoacids
combining carboxylic acid with alcohol in the presence of acid catalyst (H2SO4)
Fischer Esterification
basic nitrogen-containing compounds found in the roots, bark, leaves, berries, or fruits of plants
alkaloids
