carbonyl reactivity Flashcards
most reactive carbonyl
acid chloride
what is the pKa of an acid chloride
-7
what makes an acid chloride more reactive than an acid anhydride
it has a more stable leaving group (Cl- more stable than ethyl ethanoate
what is more reactive out of an aldehyde and ketone and why
aldehyde because of there is only 1 positive inductive effect from the alkyl group, whereas a ketone has 2 positive inductive effects making it LESS electrophilic than the aldehyde
which is more reactive out of an ester and amide and why
both are unreactive due to mesomeric effects which REDUCES the electrophilic carbon. The ESTER is more reactive though as the O is more ELECTRONEGATIVE so more electronegativity is pushed back into the molecule, restoring some electrophilicness.
trans rotamer
r groups are one the same face (eg amides)
cis rotamers
r groups face away from each other (eg amides)
how do rotamers occur in amides
mesomeric effects restricting rotation
are amides basic, and why
no because of mesomeric effects, the lone pair overlaps with the pi cloud so they can’t accept a proton
rank order of amino acids (most reactive to least reactive)
acid chloride, acid anhydride, aldehyde, ketone, ester and amide
carbonyl without a leaving group + H2O
forms a hydrate
what makes something the major product
more stable
carbonyls without a leaving group + OH
forms ketals if R is a CH3 / acetals if R is an H
how does glucose exist in water
a cyclic hemiacetal
carbonyl without a leaving group + amine (condensation reaction)
imine
