Study Flashcards
sp hybridization
bond angle
orbitals after hybridization
180° bond angle
1 s orbital and 3 p orbitals –> 2 sp orbitals and 2 p orbitals
sp2 hybridization
bond angle
orbitals after hybridization
120° bond angle
1 s orbital and 3 p orbitals –> 3 sp2 orbitals and 1 p orbital
sp3 hybridization
bond angle
orbitals after hybridization
109.5° bond angle
1 s orbital and 3 p orbitals –> 4 sp3 orbitals
Lone pair next to pi bond
Creates resonance, so the hybridization is one lower than expected
The hybridization is lower on the atom which the lone pair is connected to (see Q3a on practice midterm 1)
Abbreviation for factors affecting basicity
CHESIR
C - charge
H - hybridization
E - electronegativity
S - size
I - induction
R - resonance
Charge
in CHESIR
Greater net negative charge equals stronger base
Hybridization
in CHESIR
The higher energy hybrid is the stronger base
sp < sp2 < sp3
Electronegativity
in CHESIR
The more electronegative, the weaker the base
Use when molecules have the same structure. Less important than size
Compare elements on the same row from left to right, left being less basic and right being more basic. For elements on the same column, basicity increases from bottom up
Size
in CHESIR
Larger atoms are more stable and therefore a weaker base
Use when molecules have the same structure. More important than electronegativity
Induction
in CHESIR
Electronegative atoms pull electrons in molecules, resulting in weaker base
Does not have strong effects relative to the other factors in CHESIR. The closer an electronegative atom is, the stronger the induction and weaker the base
Resonance
in CHESIR
Results in a weaker base
How to determine major species in solution
When pH = pKa, 1:1 balance between protonated/deprotonated
When pH < pKa, the more acidic form will be favored. When pH > pKa, the more basic form will be favored
How to estimate pKa of a molecule
Look for similar atoms, charge, and resonance
Acidity on periodic table
Acidity increases from left to right and from top to the bottom
Also basicity increases from bottom up (because size increases top down, so the smaller molecules are more unstable and therefore more basic)
When looking at how basic/acidic an element would be