11/5 Flashcards
what happens to the oxygen in the carbonyl of an acetal formation
the oxygen is removed as a byproduct of water
what is the nucleophile in acid catalyzed acetal formation
an alcohol
what are the three ways to get a acetal formation to favor the products?
by using an alcohol as the solvent
-this provides more reactants which causes equilibrium to shift toward the products
By removing water as it is formed with a drying agent
-this removes the product concentration and causes the equilibrium to shift towards the products
Azeotropic distillation
-you distill alcohol and water to shift the reaction towards the products
what is the purpose of ethylene glycol
it creates a cyclic acetal which acts as a protecting group and prevents the carbonyl from reacting
what happens when we try to form an acetal from a base catalyzed mechanism?
you only form the hemiacetal, it stops there because the OH cannot be protonated to form a good leaving group
if we want to protect an alcohol in a reaction, what should we use and make?
use a Silyl protecting group (TBSCl) to create OTBS
if you only want one part of the starting material to react, how do you prevent the ketone/aldehydee from reacting if present?
use ethylene glycol to make a protecting group
do esters react to form acetals?
no, only ketones and esters
how do you remove a protecting acetal group
with hydrolysis in H30+
if you react an aldehyde or ketone with water, what is the product
hydrate
if you react a aldehyde or ketone with an alchohol, what is the product
acetal
if you react a primary amine with a ketone or aldehyde, what is the result
an imine
if you react a secondary amine with a ketone or aldehyde, what is the result
an enamine
what type of reaction is imine formation
nucleophilic addition
when creating an imine, how do we form OH into h20, a good leaving group
we do a proton transfer
