Test 2 Flashcards
which bonds are rigid
double and triple bonds
which bonds are flexible
single bonds
greater orbital size mismatch = _________ bond length
longer
greater orbital size mismatch = ________ bond strength
weaker
as pH decreases, acid strength ______
increases
as pKa decreases, acid strength ______
increases
factor of acidity =
10^ delta pKa (absolute value)
hydrocarbon definition
molecule with ONLY hydrogen and carbon atoms
what atom is going to “attack”
the LESS electronegative atom
LESS electronegative atom = less greedy, more willing to share
single bond C atom hybridization
sp3
double bond C atom hybridization
sp2
triple bond C atom hybridization
sp
weaker acid has a _____ conjugate base
stronger
stronger acid has a _____ conjugate base
weaker
requirement to be a bronstead base
at least one lone pair
requirement to be a bronstead acid
at least one hydrogen tom
electrophile (lewis acids)
A+
A incomplete octet
nucleophile (lewis base)
A- long pair
A lone pair
A=A
A=-A
term for molecule that can act as an acid or a base
amphoteric
resonance stabilization = ______ pKa
lower
aka more stable
examples of resonance stabilization
negative charge stabilized by:
- placement on electronegative atom
- electronegative atom nearby
- double or triple bond nearby
which orbital is the lowest energy
(best/most stabilizing)
sp
most unstable cycloalkane
cyclopropane
most stable cycloalkane
cyclohexane
cyclopentane is close second
why are 10+ carbon rings unstable
trans angular sterics (clash)
reasons cyclopropane is unstable
angle strain
torsional strain
reasons cyclobutane is unstable
angle strain
torsional strain
describe angle strain and torsional strain for cycloPROPANE
angle strain - too narrow, should be 109 degrees but they are 60 degrees
torsional strain - due to eclipsed (bent) bonds
describe angle and torsional strain for cycloBUTANE
angle strain - too narrow, should be 109 degrees but they are 88 degrees
torsional strain - due to eclipsed (bent) bonds, molecule becomes puckered to remove some torsional strain (butterfly conformation)
how does a double or triple bond affect planarity
atoms bonded to double or triple bonds are IN PLANE with the double or triple bond
conjugate acids have ______
more H atoms
conjugate bases have ______
fewer H atoms
