Nucleophillic addition to carbonyls
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What is the LUMO?
Lowest unoccupied molecular orbital
What is the HOMO?
Highest occupied molecular orbital
What is the key difference between c=o and c=c?
C=O is polarised
Why is there polarity in C=O
The oxygen is more electronegative than carbon which means it has a delta negative charge, leaving carbon with a delta positive
Why is nucleophilic attack able to happen?
The carbon is delta positive
What is the oxidation level?
The number of bonds from carbon to atoms other than C or H
What is found at the CO2 oxidation level?
Carbon dioxide Carbonate Tetrachloromethane
What is found at the carboxylic acid level?
Carboxylic acids Ester Acid chloride Amide Acid Anhydride Orthoester
How many bonds to heteroatom does the CO2 oxidation level have?
4
How many bonds to heteroatom does the carboxylic acid level have?
3
What is found at the aldehyde oxidation level?
Aldehyde Ketone Imine Hydrate Hemiacetal Acetal Enol
How many bonds to heteroatom does the aldehyde oxidation level have?
2
What is found at the alcohol oxidation level?
Alcohol Ether Amine Alkyl chloride Alkene
How many bonds to heteroatoms does the alcohol oxidation level have?
1
What is a pi bond equivalent to?
one bond to a heteroatom
How many bonds to heteroatom does the alkane oxidation level have?
0
What must happen if you make a bond to carbon?
You have to break one
What are the two steps in the nucleophilic addition mechanism?
• Nucleophilic attack at the carbonyl carbon 2. Protonation of the oxygen anion forming an OH group
What are the two reasons for the carbonyl carbon being electrophillic ?
• Bond polarity 2. Orbitals
How do orbitals cause an electrophilic carbonyl carbon?
Electrons are transferred from the homo of the nucleophile into the lumo of the carbonyl compound
What two orbitals make up C=O?
C-O Pi bonding orbital C-O Pi star anti bonding orbital
What are the characteristics of the C-O pi bonding orbital?
Smaller on carbon Larger on oxygen
What are the characteristics of the C-O pi star anti bonding orbital?
Bigger on carbon Smaller on oxygen
What type of reaction is cyanohydrin formation?
Equilibrium Reversible