Beruflich Dokumente
Kultur Dokumente
CARBONYL COMPOUNDS
• Aldehydes and Ketones
• Nomeclature of Carbonyl Compounds
• Nucleophilic Addition Reactions of
Carbonyl Compounds
• Reduction of Carbonyl Compounds
• Oxidation of Carbonyl Compounds
1.7 Aldehydes And Ketones
• vanillin = vanilla
• benzaldehyde = almonds
• cinnamaldehyde = cinnamon
1.7 Aldehydes And Ketones
Ketone Odors and Flavors
• acetophenone =
pistachio
• carvone = spearmint
• ionone = raspberries
• muscone = musk
1.7 Aldehydes And Ketones
Aldehydes Nomenclature
3 1
2 5 4 2
O 3
3 O
2 4
1 1
2-methylpropanal 2,2-dimethylbutanal O
2-isobutylpentanal
4 2 1
5 3
4 6 6
2
O 3 5 7
1
2-methyl-2-isopropylheptanal 2-secbutylhexanal
1.7 Aldehydes And Ketones
Ketones Nomenclature
1
O
2 5
5 7 6
1 3 7
4 2
3 4 8
6 8 9
O
3-ethyl-2-methyloctan-4-one 4-ethylnonan-3-one
or 3-isopropyloctan-4-one
7 6 O
1
5 2
5 3
O
4
6 4
3 2
1
4-ethyl-5-methylheptan-2-one 3-isobutylhexan-2-one
Exercise 41 : Name the following compounds using the
IUPAC system of nomenclature
H
O
O
O
1.7 Aldehydes And Ketones
Nucleophilic Addition Reactions of Carbonyl
Compounds
H H
Formaldehyde 2-Hydroxyacetonitrile
H3C CH3
NaCN
C O + HC N N C C OH
H3C CH3
2-Propanone 2-Hydroxy-2-methylpropanenitrile
H H
STEP 2: Protonation gives the cyanohydrin
H H
..N ..O . .
N. ..N ..OH
C C ...
- H C C C ..
H H
HCN is weak acid, not very nucleophilic because low ionize to form
CN-. Therefore, source CN- such as KCN and NaCN are used and
prepared in acid solution (H2SO4)
1.7 Aldehydes And Ketones
Hydrolysis and Reduction of Cyanohydrin
Compounds
Hydrolysis: Conversion of cyanohydrin into -
hydroxycarboxylic acids
H H O
+
H3O
HO C C N HO C C OH
heat
H H
2-hydroxyacetonitrile 2-hydroxyacetic acid
H
O
O
O
1.7 Aldehydes And Ketones
Addition of Grignard Reagents to C=O
H H
1. Ether
C O + CH3CH2 MgBr H3CH2C C OH
+
2. H3O
H H
Formaldehyde Ethyl magnesiumbromide 1-Propanol
H H
1. Ether
C O + CH3CH2CH2 MgCl H3CH2CH2C C OH
+
2. H3O
H3CH2C CH2CH3
Propanal Propyl magnesiumchloride 3-Hexanol
H3 C CH3
1. Ether
C O + CH3CH MgI H3CHC C OH
+
2. H3O
H3 C CH3
CH3 CH3
2-Propanone Isopropyl magnesiumciodide 2,3-Dimethyl-2-butanol
1.7 Aldehydes And Ketones
Mechanism Addition of Grignard Reagents to C=O
H H
C O + CH3CH2CH2 MgCl
H3CH2CH2C C O-Mg+Cl
H3CH2C
1. Ether CH2CH3
Propanal
STEP 2: The Grignard reagent attacks a carbonyl carbon to
form alkoxide salt
H H H
CH3
•Ketone will form H3C
Ni/H2 or LiAlH4
secondary alcohol C O H C OH
H3C CH3
2-Propanone 2-Propanol
1.7 Aldehydes And Ketones
Oxidation of Carbonyl Compounds
Note: ethanol, CH3CH2OH or a sec. alcohol with the group CH3CH —CH3
also give positive iodoform tests.
Exercise 44 : Draw the structural formula for compound
A, B, C and D
LiAlH4 Na2Cr2O7
A O B
LiAlH4 Na2Cr2O7
C O D
Exercise 45 : Both compound A and B are isomeric with
a molecular formula C5H10O. When A is boiled with
acidified potassium manganate (IV), a carboxylic acid
formed and the product is optically active, but B does
not react with acidified potassium manganate (IV).
When compound A and B are warmed with alkaline
iodine, only B gives a yellow solid.