Kaplan Organic Chemistry: Chapter 4 Analyzing Organic Reactions Flashcards
the more electronegative, the ___ the acidity
the HIGHER the acidity. e- density pulled away from H+, more likely to leave.
the lower the bond strength, the ___ the acidit
the higher the acidity.
periodic table trend for acidity
acidity increases going DOWN the periodic table.
higher Ka = ___ acid.
higher pka = ____ acid
higher ka = STRONGER acid
higher pka = WEAKYER acid.
formula for pka
pka= -log (Ka)
lower pka = stronger acid.
functional groups that act as bass
amines, amides
functional gorups that act as acids
aldehydes, ketones, carbox acids, CA derivatives (e/x anhydrides)
is a nucleophilic atom acidic or basic
BASIC. remember, a base is an electron donor or a proteon acceptor. it WANTS positive charge– it is nucleophilic.
the more electrons the more :
nucleophilic
the more En, the ____ nucleophilic
LESS nucleophilic. It wants e- instead– its electrophilic
nucleophilicity and steric hinderance
mulkier moleucles are LESS nucleophilic.
nucleophilicity and solvents
protic solvents INHIBIT nucleophilicity by protonating the nucleophile or hydrogen bonding.
in a protic solvent, rank the nucleophilicity of the halides
- I-
- Br -
- Cl-
- F- (least nucleophilic in a protic solvent)
F- is least nucleophilic because they are preoccupied with hydrogen bonding with the protic solvent itself.
T/F: you can conduct a nucleophile reaction in hexane
FALSE. nucleiphiles are always polar, and often carry a charge. therefore, you need a POLAR solvent, whether protic or aprotic. you CANNOT carry out a substitution nucleophilic reaction in hexane. the nucleophile MUST be able to dissolve in the solvent.
electrophiles are leis ___
acids. the more acidic, the more electrophilic. Lewis acids are electron acceptors.
the weaker the base, the more stable in solution, which increases the ___ reactivity
electrophilic.
the more positively charged, the ___ electrophilic
the more electrophilic.
name the acidity (and thus, ELECTROPHILICITY) of carboxylic acid derivatives
1) anhydride
2) CA
3) ESTER
4) amide
heterolytic reaction
when a bond is broken and BOTH electrons are given to ONE of the two products.
weak bases, aka ______, are good leaving gorups
conjugate bases of strong acids. Ex/ I-, Cl-, Br- are good leaving groups.
Sn1 reactions favors what type of carbon? What type of solvent/
Sn1 reactions favors SUBSTITUTED carbons and PROTIC solvents because it is a multi-step reactions and the carbocation can be stabilized by the solvent.
Sn2 reactions favors what type of carbon? what type of solvent?
Sn2 ractions favors LEAST SUB carbons and APROTIC POLAR solvents because it is a single step reaction and the solvent cannot be interfering with the substrates by hydrogen bonding with them. therefore, they need a substrate that cannot Hbond.
rate equation for SN2
rate = k (Nu)(RL)
Primary alcohols can be oxidized to form ___,
aldehydes
primary alcohol to aldehyde requires ___. Primary alcohol to CA requries ___
primary alcohol to aldehyde requires PCC. Primary alcohol to CA requries STRONGER OXIDIZERS (K2Cr2O7)
secondary alcohols can be oxidized to form ____
ketones.
an aldehyde can converted to a CA via
peroxide or stronger oxidizers.
oxidation reactions increase the number of bonds to
oxygen
reduction reactions increase the number of bonds to
hydrogen
how can you break an alkene into an aldehyde and a ketone
ozonolysis. O3 paired with zinc.
tertiary alcohols can undergo oxidation to ___
false. tertiary alcohols cannot undergo oxidation because all the bonds to carbon are being used up and cannot suport a double bond to oxygen.
electronegativity and its relationship to being a good reducing agent
good reducing agnets are LOWER in En. wannts to get rid of electrons, wants to get oxidized. Na, Mg, Al, Zn are all good reducing agents- they want to lose e-.
reduction of esters results in
a pair of alcohols
reduction of aldehyde
primary alcohol
reduction of ketone
secondary alcohol
reduction of amide
amine
why are alpha hydrogens more acidic in carbonyls than in regular CH bonds?
because they are resonance stabilized of the enol form.
