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COMPOUND
S
1
Objective
Describe
INTRODUCTION
Functional
INTRODUCTION
ALDEHYDE
KETONE
O -
O -
C +
C +
= alkyl, aryl @ H
Naming of Aldehyde
Aldehyde
Naming of Aldehyde
Structure
O
H-C-H
O
CH3-C-H
O
IUPAC name
General
name
methanal
formaldehyde
ethanal
acetyldehyde
propanal
propionaldehyde
CH3CH2-C-H
6
Naming of Aldehyde
Structure
O
n-butyraldehyde
pentanal
n-valeraldehyde
benzaldehyde
benzenecarbaldehyde
CH3CH2CH2-C-H
O
CH3(CH2)3-C-H
O
Ph-C-H
(phenylmethanal)
Naming of Aldehyde
O
2
CH2C-H
Phenylethanal
(phenylacetyldehyde)
CH2=CHCH2C-H
4
3-butenal
H3C-H2C O
CH3CHCHC-H
4
OH
2-ethyl-3-hydroxybutanal
Naming of Ketone
Ketone
The
Naming of Ketone
Structure
O
IUPAC name
General name
propanone
acetone
(dimethyl ketone)
CH3CCH3
O
CH3CCH2CH3
O
Butanone
CH3CCH2CH2CH3
2-pentanone
Naming of Ketone
Structure
IUPAC name
O
Ph-C-CH3
acetophenone
phenylethanone
O
Ph-C-Ph
O
CH3CH2CCH2CH3
General am
(phenyl methyl ketone)
benzophenone
diphenylmethanone
(diphenyl ketone)
3-pentanone
diethyl ketone
11
O
CH2C-CH3
CH2=CHCH2CCH3
5
2 1
4-penten-2-one
phenylpropanone
CH3CCH2CH2CCH3
1
O
-CH2C-CH21
2 3
1,3-diphenylpropanone
2 3
2,5-hexanadione
O
CH2CH3
OH
2-ethyl-2-hydroxycyclopentanone
12
EXCERCISE
1. Write the names of the following compounds according to
IUPAC nomenclature
a.
CH3
c. C H 3C H 2C H 2C H C H
CH2
CH3
b.
C H 3C H 2C H 2C
CHCH3
d. CH 3CH 2C CH2CH2CH2CH3
O
CH3
13
14
Objective
Explain
15
Preparation of
Carbonyl
Oxidation of Alcohols
1.
CH3CH2CH2CH2-OH + PCC
CH2Cl2
1-butanol
CH3CH2CH2CH=O
butanal
-OH
KMnO4
=O
H+
cyclopentanol
cyclopentanone
16
Preparation of
Carbonyl
2. Ozonolysis of alkene
CH3
(i) H3CC=CHCH3
(ii)
(i) O3
(ii) Zn/H2O
(i) O3
(ii) Zn/H2O
CH3
H3CC=O + O=CCH3
O=CH(CH2)4CH=O
17
Preparation of
Carbonyl
4. Friedel-Crafts Acylation
-a good method for preparing of aromatic
ketones
O
O
+ R-C-Cl + AlCl3
+ R-C-O-C-R + AlCl3
-C-R
O
-C-R
18
Practice Questions
(a) CH3CH(Br)CH(CH3)OH + K2Cr2O7/H2SO4
(b) CH3CH=CCH(CH3)2
CH3
(c)
(i) O3
(ii)H2O/Zn
-C=O
Cl
AlCl3
19
CHEMICAL PROPERTIES
1.
2.
3.
4.
5.
Oxidation
Reduction
Nucleophilic addition reaction
Condensation
Haloform reaction
20
Objective
To
1.0 Oxidation
Aldehydes are easily oxidised to carboxylic acid by
strong oxidising reagents e.g. KMnO4/H+ , K2Cr2O7/H+
Mild oxidising agents such as Tollens, Schiff, Fehlings
& Benedicts solutions can also oxidise aldehydes.
Ketones are resistant towards oxidation because they
do not have hydrogen attached to the carbonyl carbon
atom.
RCHO
O
RCR
KM nO4
H
KM nO 4
H
RCOOH
No reaction
22
O
+
RCH + 2[Ag(NH3)2] + OH
silver mirror
CH3CH2CHO + 2[Ag(NH3)2] + OH
-
silver mirror
O
+
CH + 2[Ag(NH3)2] + OH
O
C O
+ 2 Ag + 2 NH3 + 2NH4
silver mirror
+
24
1.2
1.2 FEHLING
FEHLING and
and BENEDICT
BENEDICT
2+ tartarate complex)
TEST
TEST(Cu
(Cu2+
tartarate complex)
Fehling
Equation;
RCHO + 4 Cu2+ + 5OH
blue
RCOO + 2Cu2O
+ 3H2O
Brick red
Example
O
O
2+
CH3CH + 4 Cu + 5OH
blue
Brick red
26
RC
H
R`- NH2
OH
RC
H
- H2O
NR
`
RCH
2.0
2.0 Reduction
Reduction
Reduction
Example:
O
CH3CH2CH
LiAlH4
H+
Aldehydes
-C-CH3
O
ketones
H2 , Ni
OH
CH3CH2CH
1o R-OH
-CH-CH 3
OH
2o R-OH
29
Reagents
H
NaCN
H2SO4
-C-OH
CN
O
CH3CHCCH3
CH3
KCN
H2SO4
OH
CH3-CH-C-CH3
CH3 CN
31
gem-diols
H+
H
C
C=O + H2O
H
H3CH2C
C=O + H2O
H 3C
OH
H+
OH
H3CH2C
OH
C
H 3C
OH
32
H+
R
C
C=O + ROH
H
H+
hemiacetal
OR
OH
C
C=O + ROH
R
OH
hemiketal
OR
33
Hemiacetal
R
H
R
R
OH
C
+ ROH
H+
OR
OR
C
OR
OH
C
+ ROH
H+
acetal
OR
OR
C
ketal
OR
34
Examples:-
OH
H+
C
C=O + CH3OH
H
CH3
H+
CH3
OH
C
C=O + CH3OH
CH3
OCH3
CH3
OCH3
35
36
Example:
HCHO
RCHO
O
RCR
(i)RMgX
(ii)H3O+
(i)RMgX
(ii)H3O+
(i)RMgX
(ii)H3O+
RCH2OH
1o Alcohol
OH
R-CH-R
2o Alcohol
OH
R-C-R
3o Alcohol
R
37
38
O
NaHSO3 +
-C-CH3
OH
-C-CH3
OSO2-Na+
Sodium
bisulphite
Bisulphite
salt
39
4.0 Condensation
NH3 & its derivatives react as nucleophile and
react with carbonyl compounds
Involved addition reaction followed by
dehydration (elimination of H2O molecule to
form C=N)
R
R
C=O + NH3
addition
R
C
R
O-H elimination R
N-H
C=NH +
H 2O
H
Carbinolamine
Unstable intermediate
40
Example:
2,4-dinitrophenylhydrazine
R
H
C=O
NNH-
-NO2
Bradys
reagent
NO2
characteristic
reaction of
carbonyl
compounds
R
C=NNH-
-NO2 + H2O
R
NO2
yellow @
orange
precipitate
41
NH3
derivatives
Name
R-NH2 @
primary
amine
C=N-R @
NH2NH2
hydrazin
e
C=NNH2
Hydrazone
NH2-OH
hydroxyl
amine
C=N-OH
oxime
Ar-NH2
Product
Name
imine
C=N-Ar
42
NH3
derivatives
NH2NHC6H5
O
NH2NHCNH2
Name
phenyl
hydrazin
e
Product
C=NNHC6H5
O
semi
carbazide C=NNHCNH2
Name
phenyl
hydrazone
semi
carbazone
43
5. Iodoform reaction
Reagent : I2 in NaOH(aq), heat forms
NaIO(Sodium iodate (i))
Formation of yellow precipitate, CHI3 ,
indicate that organic compound consist
of methyl carbonyl or methyl alcohol:OH
O
-C-CH3
-C-CH3
H
44
GENERAL REACTION:-
O
RCCH3
OH
RCHCH3
I2
OH-
I2
OH-
O
RCCH3
O
RCCI3
I2
OH-
OH
O
RCCI3
O
RCO- + CHI3
OH
O
RCO- + CHI3
45
EXAMPLE:-
O
CH3CH2CCH3
NaIO
CH3CH2C-O- + CHI3
O
-C-CH3
I2 / NaOH
-C-O-
+ CHI3
46
EXAMPLE:-
O
H-CCH3
I2/NaOH
O
H-C-O- + CHI3
OH
-C-CH3
I2 / NaOH
-C-O-
+ CHI3
47
Practice Questions
(a) CH3CCH2CH3 + H2NNH
O
(b) CH3CCH2CH3 + H2NOH
NO2
H+
NO2
H+
O
(c) CH3CCH2CH3 + I2 / NaOH
O
(d) CH3C-CH2-Ph + LiAlH4
O
48
Practice Questions
The molecular formula of an unknown compound A is C 7H14.
Ozonolysis of A gave two products B and C, whereby both
B and C reacted with 2,4-dinitrophenylhydrazine to give
solid derivatives. B gave positive results to Tollens and
Iodoform tests, while C gave negative result to both of
the tests. Suggest the structural formula of A, B and C.
Explain your answer.
49