The Carbonyl Bond Flashcards
general carbonyl containing compounds
ketone, aldehyde
carboxylic acid derivatives
ester, acid chloride, acid anhydride, amide
uses of carbonyl chemistry
medicinal and agrochemistry
mechanistic chemistry
biological chemistry
chemicals with oxidation level 1
alcohol, amine
what causes oxidation level 1
one bond to the heteroatom
define heteroatom
an atom which is not a carbon
molecules with level 2 oxidation
aldehyde, ketone, imine
what is an imine
double bond to nitrogen with another bond to a R on the nitrogen
molecules with level 3 oxidation
carboxylic acid, acid chloride, acid anhydride, ester, amide, nitrile
what causes the C - O pi bond on the C=O bond
overlap of the up down figure of 8 p orbitals on the C and O
what creates the C - O sigma bond in the C=O bond
overlapping sp2 hybridised orbitals from the C and the O
steps to drawing a good MO for C=O
one in bottom row and three in top row on outside for C and O atoms
O ones slightly lower
three mixed sp2 orbitals between these rows in the middle
one in line with top row for unhybridised with one atom in
in very middle, lowest sigma, pi between mixed sp2 and unhybridised both full
pi and sigma antibonding in very middle at top above everything else
connect sigmas to hybridised and pis to unhybridised
does C - O or C = O have lower bond energy
C - O
is C - O or C = O higher energy bond
C = O
does C or O have lower electronegativity
C
why is C = O still quite reactive
bonding orbitals are skewed to carbon whereas antibonding are skewed to oxygen
which atom is delta positive in C = O bond
Carbon
what is the angle of attack of a nucleophile on a carbonyl
107 degrees
which energy levels interact when nucleophile attacks carbonyl
LUMO of carbonyl with HOMO of nucleophile
what sort of bonds are the LUMO of carbonyl
antibonding orbitals
what is the shape of the carbonyl after it has been attacked
tetrahedral
hybridisation of carbon after nucleophilic addition
tetrahedral
