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6 groups
sp3d2
5 groups
sp3d
4 groups
sp3
3 groups
sp2
2 groups
sp
more s-character an atom has in a bond…
the bond is shorter and stronger
more resonance contributors means…
more stable
covalent bond (instead of an ionic bond) means electronegativity difference of ___ or less
2.0
heteroatom
any atom not Carbon or Hydrogen
difference between resonance structures and isomers?
resonance structures differ in electron placement, while isomers differ in both electron and atom arrangement
bond length and atom size ptable trend
decreases across a row, increases down a column
bond angle and shape for an atom surrounded by 2 group
linear, 180 degrees
bond angle and shape for an atom surrounded by 3 groups
trigonal planar, 120 degrees
bond angle and shape for an atom surrounded by 4 groups
tetrahedral, 109.5 degrees
tetravalent
having a valence of four
ground state
lowest energy arrangement of electrons for an atom
hybridization
mixing atomic orbitals from same atom to form hybrid orbitals
single bonds have ___ type of bonds
sigma
are bonds formed from orbitals stronger or weaker than p orbitals
stronger
in double and triple bonds, which bonds are hybridized?
sigma bonds are overlapped by hybridized orbitals. pi bonds are formed by overlap of unhybridized p orbitals
# electrons between two nuclei increases… bonds are
shorter and stronger
a _ bond is weaker than a _ bond
pi, sigma
electronegativity ptable trend
increases across row, increases up a column
BL acid is a proton
donor
BL base is a proton
acceptor
BL acid criteria
must contain hydrogen and a proton +, 0, or - , only one starting material has Hydrogen
BL base criteria
must be able to bond to a proton 0 or - net charge, one material has lone pairs or pi bonds.
Larger Ka means
stronger acid
Larger pKa means
weaker acid
deprotonate
removing a proton from a molecule, ion, or compound
equilibrium favors the formation of
weaker acids and bases
how to know if the base can deprotonate the acid?
if conjugate acid of a base is weaker than the original acid, the base would be strong enough because the equilibrium would favor the products
carbanions
negative charge on carbons
elemental effects
acidity of H-A increases left to right across a row and down a column of a periodic table (electronegativity trend)
inductive effects
more electronegative atoms means higher acidity of H-A b/c they stabilize regions of high e- density by an electron withdrawing effect
resonance effects
acidity of H-A increases when conjugate base has a resonance
hybridization effects
H-A acidity increases as the conjugate base percent s-character increases
sp s%
50%
sp^2 s %
33%
sp^3 s %
25%
sp^3d %
20%
sp^3d^2 %
16.67%
sp^3d^3 %
14.29%
Lewis acid
e- pair acceptor
Lewis base
e- pair donor
electrophiles are usually
Lewis acids
identifying lewis bases
contain lone pairs or pi bonds, can donate an electron pair
identifying Lewis acids
most have protons, have an unfilled valence shell, polar covalent bond, partial + charge
hydrocarbons
compounds made up of only hydrogen and carbon
hydrocarbons include…
alkane, alkene, alkyne, aromatic compound
Type of compound?
Alkane
Type of compound + functional group?
Alkene, double bond
Type of compound + functional group?
Alkyne, triple bond
type of compound + fgrp?
aromatic compound, phenyl group
which compound of a hydrocarbon is notoriouslly unreactive?
alkanes
Compounds w/ C-Z sigma bonds
Alykl halide, alcohol, amine, thiol, ether, sulfide
compound + fgrp?
alkyl halide, -x halo group
cmp + fgrp?
alcohol, -OH hydroxy group
cmp + fgrp?
ether, -OR alkoxyl group
cmp + fgrp?
amine, -NH2 amino group
cmp + fgrp?
thiol, -SH mercapto group
cmp + fgrp?
sulfide, -SR alkyhtio group
cmps containing C=O group
Aldehyde, amide, acid chloride, carboxlyic acid, ketone, ester
cmp?
aldehyde
cmp + fgrp?
ketone, carbonyl group
cmp + fgrp?
carboxylic acid, carboxy group
cmp?
ester
cmp?
amide
cmp?
acid chloride
what is a functional group?
atom or group of atoms comprised by similar physical/chemical reactive properties
IMFS increasing strength
van der waals, d-d, hydrogen, Ion-ion
as surface area increases
larger attractive force between two molecules, stronger IMFS
bonds to look for in a hydrogen bond
O-H, N-H, or H-F
how to know if a molecule exhibits dipole-dipole
polar molecules present
IMFS and boiling point trend
higher IMFS means higher BP (note: same trend w larger surface area, and being more polarizable)
volatility and bp trend
lower bp is more volatile, higher bp less
more compact compoundmeans..
less surface area, lower boiling point, higher melting point
IMFs and Melting Point trend
higher IMFs, higher MP
other melting point trend
as symmetry (roundness) increases, melting point increases
criteria for a compound to bond to another molecule like itself?
O-H or N-H bond
criteria for a compound to bond to water?
an O or N atom
water solubility criteria
Water soluble only if it contains one polar functional group capable of five hydrogen bonding w/ the solvent for every carbon it has (look for O, N)
polar and nonpolar compounds dissolve in
polar and nonpolar solvents
water solubility rule for organic compound with one functional group
less than or equal to five C atoms and has an O or N atom
nonpolar parts of molecules are usually
hydrophobic
polar parts of molecules are usually
hydrophilic
covalent compounds are generally____ in organic solvents
soluble
ionic compounds are generally ____ in organic solvents, but __ in water
insoluble, soluble
soaps have…
a long hydrocarbon chain and carboxylic acid salt
which compounds can pass through the lipid membrane easier and why?
non polar or weaker polar substances can easier because they can interact with the hydrophobic interior of the phospholipid structure
what cannot pass readily through the membrane?
larger polar atoms, and ions
what makes a heteroatom nucleophilic?
lone pairs, pi bonds make nucleophilic sites
what makes a heteroatom electrophilic
electronegative atoms like N, O, or X make a carbon atom an electrophile
two resonance structures differ ONLY IN
the position of nonbonded e- and pi bonds
what is the most stable type of resonance structure & why?
resonance hybrid is the most accurate and most stable resonance structure b/c electron density is delocalized (less charges)
what makes a resonance structure a better contributor?
less charges
s% and electronegativity trend
higher s% means more electronegative
how are “x” degree carbons classified by?
the # of carbons bonded to them
how are “x” degree hydrogens classified by?
classified by the degree of carbon they are attached to (how many carbons are attached to the carbon they are attached to)
how are alkyl halides and alcohols “x” degree classified by?
the degree of carbon their OH or X group is attached to
Note
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