Organic I - carbonyl chemistry intro

What is the carbonyl functional group?

• C=O

• Most common reactive functional group

What functional groups contain a carbonyl?

• Aldehydes

• Ketones

• Carboxylic acids

• Esters

• Amides

• Acid anhydrides

• Acid chlorides

• Urethane

• Ureas

• Imides

• Carbonates

• Chloroformates

How is the carbonyl group formed and how does this affect its reactivity?

• Unhybridised 2p orbitals overlap between C and O to form the pi bonds

• O contains two lone pairs in sp2 orbitals - used to react

What is the geometry of the carbonyl group?

• C=O is in the plane - trigonal planar

• Other substituents are above and below the plane

How is the carbonyl group polarised?

• O is more electronegative than C so causes a polar bond

• Greater level of electron density on O (delta -) than C (delta +)

How does the oxygen of the carbonyl react?

• Nucleophilic part (2 lone pairs)

• Attacks electrophiles

How does the carbon of the carbonyl react?

• Electrophilic

• Attacked by nucleophiles