chapter 26 Flashcards
secondary alcohols are oxidized to? and under what conditions
ketones
refluxed under acidified conditions
the oxidizing agent in the oxidization of secondary alcohols
potassium dichromate
primary alcohols are oxidized to what, and under what conditions
oxidizing agent?
aldehydes
distilled under acidic conditions
potassium dichromate
can tertiary alcohols be oxidised
no
what group is present in the structure of both aldehydes and ketones
a carbonyl group
the position of the carbonyl group in a ketone and aldehyde
in a ketone, the carbonyl group is joined to two different carbons in the chain, while in aldehydes, the carbonyl group is found at the end of the carbon chain
the ending of a molecular structure of an aldehyde
CHO
aldehydes are oxidized to
carboxylic acids
conditions for the oxidization of aldehydes and the oxidizing agent
reflux under acidic conditions
potassium dichromate
when an aldehyde is oxidized, there is a color change in the dichromate solution from
orange to green
do ketones undergo oxidization
nope
why is the C=O bond polar
because of the difference in electronegativity values of O and C
nucleophile
a electron donor
aldehydes and ketones can be reduced to
the reducing agent for such reactions?
alcohols
sodium tetrahydridoborate (III) (NaBH4)
in nucleophilic addition, the C=O pie bond breaks in a ……………. manner forming a …………….. charged intermediate
heterolytic
negatively
in nucleophilic addition, the hydride ion is provided by
the NaBH4
Describe what happens in nucleophilic addition
lone pair on the hydride ion is attracted and donated to the partially positive carbon atom of the C=O bond. This forms a dative covalent bond
in nucleophilic addition, the C=O pie bond breaks in a heterolytic manner forming a negatively charged intermediate
the oxygen atom in C-O bond in the intermediate donates a lone pair of electrons to a hydrogen atom in a water molecule.
An alcohol is formed as a result
an aldehyde reacts with hydrogen cyanide to form
under what conditions
where do we get the hydrogen cyanide from
a hydroxynitrile
acidic conditions
NaCN
why is the reaction between an aldehyde and hydrogen cyanide important
it provides a way to extend the carbon chain length
on which atom is the lone pair in CN on
on C
brady’s reagent
a solution of 2,4-DNP dissolved in methanol and sulfuric acid
describe a test to identify a carbonyl group in either an aldehyde and a ketone
add a 5cm depth of a solution of 2,4-DNP to a clean test tube
add 3 drops of the unknown compound. leave to stand
a yellow/orange precipitate forms if there is a carbonyl group(aldehyde or ketone) present
if no crystals form when brady’s reagent is added to a solution containing a ketone or an aldehyde
add more sulfuric acid
how do we identify whether a carbonyl group is exactly in a certain molecule
the precipitate formed after adding Brady’s reagent is filtrated
then it is recrystallized
the melting point is then measured and compared with known values
tollen’s reagent
a solution of silver nitrate in aqueous ammonia
in the tollen’s reagent, what acts as the oxidizing reagent
Silver ions