Kaplan Organic Chemistry Chapter 3
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quantum number l
- ranges from 0 to n-1
- l values 0, 1, 2, 3 represent s, p, d, f
quantum number m
ranges from -l to l
what does a double bond and a triple bond consists of?
- double bond: one sigma and one pi
- triple bond: one sigma and two pi bonds
one sigma and 3 pi bonds
- hybridization in alkenes
- third p-orbital is left unhybridized (to participate in pi bond)
- the electron density in a molecule is the weighted average of all possible resonance structures
- potential arrangement of electrons in molecule
- one s orbital hybridizes with one p orbital to form two sp-hybridized orbitals
- the two unhybridized p-orbitals form two pi bonds.
what is the condition for acid and base reaction to occur?
if the conjugate base of the acid and the conj acid of base are weaker than original reactants
coordinate covalent bond
covalent bonds in which both electrons in the bond came from the same starting atom.
bronsted lowry definition of acid and base
donate proton (acid)
water can acts as either bronsted lowry acids or bases
- products / reactants
- pKa below -2 are strong acids
what is the relationship of acidity with electronegativity?
acidic ability increases with more elctronegativity
increase in bond strength, what happens to acidity?
- decrease in acidity
- bond strength takes precedence when compared to electronegativity
is nucleophile strength a kinetic or thermodynamic property?
factors that determine nucleophilicity
- charge (more neg better)
- electroneg (more, bad)
- steric (bad)
- solvet (protic can inhibit)
what is nucleophile trend in polar protic solvents
- nucleophility increase down the PT
- in protic solvents, F- is the least nucleophilic (down the column)
- in aprotic solvents, F- is the most nucleophilic down the column
which functional groups are the most electrophilic?
anhydrides, followed by carboxylic acids and esters and then amides.
bond is broken and both electrons are given to one of the two products
what are good leaving groups?
- best able to stabilize electron set of electrons
- LG ability is augmented by resonance and inductive effects from electron-withdrawing groups.
- water is a good LG
- two steps first is rate limiting
- postively charged carbocation
- first order reaction depends on k[R-L], alkyl group with leaving group
- anything that accelerates the formation of carbocation will increase the rate of Sn1 reaction
- product is racemic (can attack from either direction)
- concerted reaction
- nucleophile must be strong, substrate cannot be sterically be hindered
- the less substituted the carbon the more reactive it is.
- rate is dependent on both nuclephile and leaving group (substrate)
- inversion of configuration
what condition allows substitution to occur?
when nucleophile is stronger basethan LG
what can primary alcohols be oxidized to?
- aldehyde or further oxidized to be carboxylic acids.
- can be accomplished by using strong oxidizing agents (Na2Cr2O7 or K2Cr2O7)
- can be made to stop at aldehyde by using PCC
what are secondary alcohols oxidized to?
amides are reduced to what?
reduction rxns are endothermic or exothermic?
which is more reactive toward nucleophiles? ketones or aldehydes?
aldehydes b/c they have less steric hindrance.
aldehyde mixed with diol
becomes acetal (protecting group)
what is the order of decreasing oxidation state?
- less bonded to oxygen
- carboxylic acid, aldehyde, amine and alkane
which oxygen cannot undergo oxidation states?
tertiary ones b/c it needs to form additional bonds with oxygen while losing bonds with hydrogen
which solvent is not useful for electrophilic and nucleophilic reactions?
nonpolar, b/c the nucleophile is always polar and nucleophile need to be able to dissolve in solvent
which conversion from carboxylic acid derivative is not possible by nucleophilic reaction
- order: anhydrides> carboxylic acid and esters>amides
- derivatives of higher reactivity can form derivates of lower reactivity but not vice versa
- nucleophilic attack on ester cannot result in formation of anhydride b/c anhydrides are more reactive than esters.
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