ALDEHYDES AND KETONES

Carbonyl group (oxo-group) is the group found in aldehydes and ketones (also in carboxylic acids) … C=O
- At the end of the chain in aldehydes (so it has at least one hydrogen attached to it)
- Somewhere in the middle of the chain ketones (so it has two alkyl groups attached to it)
- They can be each other’s isomers, so it is impossible to distinguish them by their molecular formula
o For example, both propanal and propanone have the same formula – C 3H6O
- They are therefore represented using displayed or structural formulae
- When naming molecules the importance goes: aldehyde < ketone < alcohol
o For more important group you write suffix, for less important group prefix

Suffix for aldehydes is -al (prefix- formyl)

- When aldehyde side group (-CHO) is attached to a cyclic molecule, it is referred to as a carbaldehyde-group
o For example, Benzencarbaldehyde (benzaldehyde) (flavouring agent in imitating almond flavour)

Suffix for ketones is -one (prefix- oxo)

- There are two ways of naming ketones
o With their number of carbons in chain, suffix and number of carbon with oxygen
 For example, hexan-2-one, propanone
o Naming the alkyl groups attached to the carbon with oxygen
 For example, methyl(butyl) ketone, dimethyl ketone

Properties of aldehydes and ketones

- The carbonyl group is polar due to the greater electronegativity of oxygen (3.4) than carbon (2.6)
o Oxygen is slightly negative while carbon is slightly positive
o Some chemical properties result from this polarity
- This allows them to form hydrogen bonds with water molecules (NOT with themselves), meaning that they
are soluble in water
o But as size increases, solubility decrease (the same principle as with alcohols)
- They are held together only by dipole-dipole interactions, which are weaker than hydrogen bonds (between
alcohols) … Meaning that their boiling point is lower than that of alcohols of similar mass
o Because of that formaldehyde (methanal) is gas, while methanol is liquid (think bout that!)
o But don’t be mistaken alcohols too have dipole-dipole interaction, but they are arbitrary in
comparison to the strength of their hydrogen bonds!

Random facts: formaldehyde is toxic gas (in plywood ig?), formalin is 40% solution of formaldehyde in water (used
for preservation), acetone is an excellent solvent and the simplest ketone!

Reactions
- They can be reduced back to alcohol
o Aldehydes to primary alcohols
o Ketones to secondary alcohols
- Aldehydes can be oxidized to carboxylic acids (aldehydes are more reactive than ketones)
- The positive charge on the carbon atom makes it open to attack by nucleophiles (O= electrophile)

Reactions we need to know, I guess? REDUCTIONs (1st of ketone, 2nd of aldehyde)

- But-2-one reacting with hydrogen cyanide (reducing agent, CN- - H+) yielding 2-hydroxy-2methylbutanenitrile
o CN- (nucleophile attacks) attaches to the C (electrophile) with positive charge on but-2-one
o But-2-one’s double bond with oxygen breaks, meaning oxygen has negative charge
o Negative oxygen makes bond with H+ … The END
- Propanal reacting with sodium borohydride (reducing agent, Na+ - BrH4-) yielding propanol
o We are looking only at the BrH4-, which would be better off (neutral) with only 3 hydrogens
o So, it gives one H- to propanal’s slightly positive carbon, propanal’s double bond with oxygen breaks,
meaning the oxygen has negative charge
o Negative oxygen makes bon with H+ from the solution itself making propanol (primary alcohol)