Topic 17B: Carbonyl Compounds

Overview
Boiling Point
Only have London and Dipole-Dipole due to polar C=O
Higher than alkane/alkene
Lower than alcohol and carboxylic acids
Solubility
Can form H-bonds- short chains dissolve
Propanone= Organic Solvent
C=O-Trigonal Planar, single optical isomer cannot be obtained >> racemic mixture
Preparation
Aldehydes
- Primary alcohol-excess
- Electric heater
- Temp- higher than alcohol/lower than aldehyde
- Exothermic reaction- maintains temp, no further O
- Orange to green
- Crystallisation- redistiallation
Ketones
- Secondary alcohol-excess
- Reflux condenser>> boil 15 mins>>distillation
- Orange to green
REACTIONS
Nucleophilic addition reactions

1) HCN + Ph8 + Catalyst Hydroxynitrile + CN+

-

Preparation of HCN
KCN + HCN, KCN + H2SO4, HCN + NAOH-h20
Racemic mixture produced
Hydroxynitriles>> hydrolysis>> carboxylic acids
>> reduced >> Hydroxyl amines

1) Reduction
-LiAlH4
-Ether solution
- product = alcohol P/S
- X + 2O >> ROH
- Can be reduced by Ni/H2

Addition-Elimination Reactions
1)
- They react with H2N- compunds
- 2,4-DNP
- Insoluble product

Bradys reagent: alphiatic - yellow aromatic- orange

Methodology - react-filter - recrystalise with alocohol - dry- data book
Product= benzene + H20

Oxidation reactions of aldehydes

Fehlings/Benedict > Blue to Red > CU20
Tollens Reagant > NAOH+AgNO3+NH3 > silver mirror
K2CR307 > orange to green > Cr +3
Potassium manganate
H+ >>>> PURPLE >>> COLOURLESS >>> MN2+
OH- AND NEUTRAL >>>PURPLE >>> BROWN PPT>>> MNO2