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Lecture 1
Molecular Structure
64
Organic Chemistry
Undergraduate 4
06/24/2011

Additional Organic Chemistry Flashcards

 


 

Cards

Term
what are the three rules for forming Lewis Dot Structures
Definition

find the total number of valence electrons in the entire molecule

 

use one pair of electrons to form one bond between each atom

 

use the remaining electrons to fill the duet rule for hydrogen and the octet rule for other atoms

Term
what is one exception to the Lewis Dot structure
Definition
when an atom has more or less valence electrons to fulfill the octet rule
Term
is it true that halogens other than flourine can make more than one bond
Definition
true
Term
when determing formal charge, what are two specific things to remember
Definition

(1) a bond between two atoms corresponds to one electron for each atom

 

(2) formal charge is the number of electrons in an isolated atom minus the number of electrons in the molecule

Term
how do you find the index of hydrogen deficiency
Definition

if it is an alkane, use: 2n +2

x= the number of hydrogens in the compound

 

[(2n+2)-x]/2

 

for any saturated alkane, this equation will equal zero

Term
what is an alkane
Definition
carbon-carbon single bond or methane
Term
what is an alkene
Definition
carbon-carbon double bond
Term
what is an alkyne
Definition
carbon-carbond triple bond
Term
meth-
Definition
1
Term
eth-
Definition
2
Term
prop-
Definition
3
Term
but-
Definition
4
Term
pent-
Definition
5
Term
hex-
Definition
6
Term
hept-
Definition
7
Term
oct-
Definition
8
Term
non-
Definition
9
Term
dec-
Definition
10
Term
give some of the IUPAC rules
Definition

longest continuous chain is the base name

 

the end carbon closest to the carbon with a substituent is always the first carbon-if there is a tie, look for the next closest substituent

 

substituents are given the same number as their carbon

 

substituents are listed alphabetically

 

 

Term
what creates molecular bonding
Definition
electrostatic force from the negative charge of electrons and the positive charge of the nuclei
Term
when are electrons at their lowest energy
Definition
when they are closest to a positive charge or farthest from a negative charge
Term
what is bond energy
Definition
bond energy is the average energy to break the bond, therefore: the higher the bond energy the more stable the compound
Term
what is a coordinate covalent bond
Definition
a coordinate covalent bond is when a single nuclei can donate both electrons
Term
what is a sigma bond
Definition

this occurs between two bonding atoms and is a single bond.

 

it has the lowest energy and is the most stable form of a covalent bond

Term
what is a pie bond
Definition
a pie bond occurs when additional bonds form between two sigma bonded atoms
Term
where do pie bonds form
Definition
above and below the sigma bonds
Term
how do sigma and pie bonds relate in bond strength
Definition
pie bonds are weaker than sigma bonds
Term
how is bond strength related to bond length
Definition
they are inversely proportional; the smaller the bond length, the greater the bond strength
Term
which is more reactive, pie or sigma bonds
Definition
pie bonds, because they are further from the nuclei and have higher energy states, therefore, more unstable and more reactive
Term
what are the several types of hybrid orbitals
Definition
sp, sp2, sp3
Term
how can you determine the type of hybrid orbital present in a compound
Definition

count the number of sigma bonds and lone pairs of electrons and match this with the superscript

 

remember that s has one orbital to fill and p has three orbitals to fill

Term
what is the character of an sp hybrid orbital
Definition
50% s and 50% p
Term
how can you determine the stability of a molecule using characters of their orbital
Definition
the more s percentage that is in it's character means the shorter the bond lengths and the more stable the molecule is
Term
what can distort predicted bond angles
Definition
lone pairs, pie bonds & ring strain
Term
what are four rules for resonance structures
Definition

atoms must not be moved- move electrons not atoms

 

number of lone pairs must stay constant

 

all resonance atoms must lie in the same plane

 

onnly applicable for pie bonds (just for MCAT purposes)

 

only proper Lewis Dot Structures

Term
what are two conditions to look for in resonance structures
Definition

a species must contain an atom with a p orbital or an unshared pair of electrons

 

that atom must be single bonded to another atom with a double bond or triple bond (in other words- a conjugated system)

Term
with ring structures, resonance is only applicable if
Definition
Huckel's rule is fulfilled (aromatic test: 4n+ 2) and so are the four basic steps
Term
when a molecule has a dipole movement it is refered to as
Definition
polar
Term
when a molecule does not have a dipole movement it is refered to as
Definition
non-polar
Term
what is an induced dipole and how does it compare to permant dipoles
Definition

an induced dipole occurs when a polar molecule or ion creates an electric field, which pushes the electrons and nuclei in opposite directions

 

these are generally weaker than permant dipoles

Term
what are instantaneous dipoles
Definition
can existed nonpolar molecules because at any moment the electrons in orbital may not be exactly between two bonds and thus induce an instantaneous dipole-that can induce additional dipoles in neighboring molecules
Term
give an example of intermolecular attractions
Definition
hydrogen bonding- a positively charged part of a molecule is attracted to a negatively charged part the same molecule and they bind- typically very weak bonds
Term
what is a London Dispersion Force
Definition
the weakest dipole-dipole force that is between to instantaneous dipoles
Term
intramolecular and intermolecular forces are
Definition
electrostatic
Term
high bond energy equals
Definition
very low energy and is a stable bond
Term
what is the easiest way to distinguish between conformational isomers
Definition
use Newman projections: eclipsed, fully eclipsed, gauche, anti- staggered
Term
what is a structural isomer
Definition
a structural isomer has the same molecular formula but different connectivity
Term
what are stereoisomers
Definition
stereoisomers have the same molecular formula and have the same connectivity as each other
Term
how can you determine if a molecule is chiral
Definition
a chiral molecule has four different substituents
Term
in absolute configuration, what directions do R and S go
Definition
R is clockwise, and S is counter-clockwise
Term
in absolute configuration, what is given highest priority and lowest priority
Definition
it is based on atomic weight- the higher the weight, the greater the priority
Term
what is relative configuration
Definition
when two molecules resemble each other except for one substituent
Term
what is observed rotation
Definition
the direction and degree to which a compound rotates plane-polarized light
Term
what does a polarimeter do
Definition
screens out photons with all but one orientation of electric field
Term
compounds that are optically inactive are
Definition

compounds that do not orient themselves in any single orientation, leaving the net force equal to zero

 

also called a racemic mixture

Term
what are the symbols for optically active
Definition
+ and "d"; - and "l"
Term
stereoisomers must contain at least one what
Definition
chiral center
Term
enatiomers have the same chemical and physical properties except for
Definition
reactions with chemicals and direction they polarize light
Term
give three examples of diastereomers
Definition
geometric isomers, cis and trans isomers
Term
what predictions can be made concerning the melting and boiling points of geometric isomers
Definition
due to their molecular dipole movement, cis isomers have a higher probability of intermolecular attractions, thus the boiling point for cis isomers is higher than trans.  however, due to their lack of symmetry, cis isomers have a lower melting point because they do not form crystals
Term
steric hindrance in cis molecules produces
Definition
higher energy levels resulting in high heats of combustion
Term
what is the maximum number of optically active isomers a single compound can have
Definition
2 ^n
Term
meso compounds are achirl, wh? and what does this mean
Definition
meso compounds are achirl because they have two chiral centers that offset each other making them optically inactive
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