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Organic Chemistry

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by

Abd Hafiz

on 15 August 2013

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Transcript of Organic Chemistry

ORGANIC
CHEMISTRY
C
H
H
H
CnH n+
2 2
ALKANES
Reactions
combustion
alkane + O
2
CO + H O
2
2
halogenation
alkane + halogen
halo-alkane + H-
/ uv
(F /Cl /Br /I )
C
F/Cl/Br/I
H
H
H
C
H
H
C
H
H
CnH n
2
ALKENES
double bond
unsaturated
naming starts at nearest double bond
Reactions
hydrogenation
alkene + H
2
alkane
halogenation
alkene + halogen
halo-alkane
(F /Cl /Br /I )
(catalyst: Ni)
inert solvent:
carbon tetrachloride
C
F/Cl/Br/I
H
H
C
H
H
H
alkene + halogen
halo-alkane & halo-hydrin
(F /Cl /Br /I )
water
halohydrination
minor
major
hydrohalogenation
alkene + H-F/Cl/Br/I
(catalyst: H SO )
2 4
halo-alkane
reactivity :
HF < HCl < HBr < HI
with acidified water
alkene + H O
alcohol
with concentrated H SO
2 4
alkene + H SO
2 4 (CONC)
hydrolysis
alcohol
C
F/Cl/Br/I
H
H
H
C
H
H
C
F/Cl/Br/I
H
H
H
C
H
H
C
OH
H
H
H
C
H
H
C
F/Cl/Br/I
H
H
H
C
H
H
C
OH
H
H
H
C
H
H
C
OH
H
H
H
C
H
H
Test
Br
inert
solvent
+
2
alkenes
halo-alkane
(decolourrised)
alkenes
KMnO
4
cold
dilute
alkaline
(decolourrised)
Mn O
diol
Baeyer's test
alkenes
KMnO
4
hot
acidified
(decolourrised)
.
CO /
.
2
Br in inert solvent / Br water
C
H
H
C
ALKYNES
C
H
H
H
C
F/Cl/Br/I
H
H
H
CnH n-
2 2
Reactions
hydrogenation
alkyne + H
2
alkane
halogenation
alkyne + halogen
halo-alkane
(F /Cl /Br /I )
(catalyst: Ni)
hydrohalogenation
alkene + H-F/Cl/Br/I
halo-alkane
nearest triple bond
triple bond
unsaturated
linear shape
naming starts at

single bond
saturated
soluble in inert solvents but not in water

C
H
H
H
C
OH
H
H
CnH n+ OH
2 1
ALCOHOLS
OH group
naming starts
at nearest
types :
1


primary
2
secondary
3
tertiary
C
H
C
OH
H
H
H
C
OH
H
R
R
C
OH
H
R
R
C
OH
R
R
Reactions
hydrohalogenation
alcohol + H-F/Cl/Br/I
halo-alkane + H O
with PCl / PCl / SOCl
alcohol
halo-alkane
0
0
0
2
3 5 2
oxidation (dehydrogenation)
alcohol + oxidizing agent
(1 ) aldehyde
(2 ) ketone
(3 ) [no reaction]
acidified KMnO / K Cr O / H CrO
4 2 2 7 2 4
O
O
O
carboxylic acid
dehydration
alcohol
alkene + H O
2
2 4
(catalyst: H SO )
2 4
reactivity
HF < HCl < HBr < HI
reactivity
1 < 2 < 3
O O O
with active metals
alcohol + K / Na / Li
metal-oxide + H
2
Test
Lucas' test
O
2 alcohol
ZnCl
2
conc. HCl
1 alcohol
O
ZnCl
2
conc. HCl
3 alcohol
O
ZnCl
2
conc. HCl
akyl halide
akyl halide
akyl halide
akyl halide
akyl halide
akyl halide
akyl halide
akyl halide
akyl halide
akyl halide
mins
5
immediately
mins

C
H
H
H
C
X
H
H
CnH n+ X
2 1
HALO-ALKANES
oxidation test
1 / 2 alcohol
KMnO
4
hot
acidified
(decolourrised)
O O
K Cr O
2 2 7
1 / 2 alcohol
O O
iodoform test
I
2
NaOH
+
CHI
3
methyl alcohol group
C
H
H
H
H
C
H
H
C
R
H
H
H
major
minor
H
H
major
minor
C
R
H
O
C
F/Cl/Br/I
H
H
C
H
H
H
2 4
reactivity :
HF < HCl < HBr < HI
C
R
R
O
ALDEHYDES
KETONNES
&
synthesized by oxidation of alcohols
pleasant tastes and aromas
naming starts at nearest C=O group
oxidation
aldehyde + 2Ag(NH ) + OH
RCOO + 2Ag + 2NH + 2NH
2
3 2
+ -
4 3
- +
Tollen's reagent (silver mirror test)
Fehling's reagent
aldehyde + Cu(ii)
RCOO + Cu O + 3H O
-
2 2
deep blue sol.
brick-red deposit
decolourised acidified KMnO
iodoform test (for ethanal)
ethanal + 3I + NaOH/KOH
CH COONa + CH I + 3HI
3 3
2
yellow precipitate
o

Reactions
catalytic hydrogenation
ketonne + H
2 alcohol
2
O
(catalyst: Ni/NaBH /LiAlH )
4 4
Grignard reagent
ketonne + RMgX
3 alcohol
O
ether
ether
Reactions
catalytic hydrogenation
aldehyde + H
1 alcohol
2
O
(catalyst: Ni/NaBH /LiAlH )
4 4
Grignard reagent
formaldehyde/aldehyde + RMgX
(formaldehyde) 1 alcohol
(aldehyde) 2 alcohol
O
O
iodoform test
ketonne + 3I + NaOH/KOH
2
CH COONa + CH I +3HI
3 3
C
R
O
OH
CnH n+ COOH
2 1
CARBOXYLIC
ACID
sour taste
weak acids : -citric acid
-methanoic acid=formic acid
-ethanoic acid=acetic acid
made by oxidation of aldehydes & alcohols
Reactions
neutralisation
carboxylic acid + base
salt + H O
2
with reactive metals
carboxylic acid + metal
salt + H
2
with hydrogen carbonates
carboxylic acid + hydrogen carbonate
salt + H O + CO
2 2
reduction
carboxylic acid + LiAlH
1 alcohol + H O
2
O
O
ether
4
esterification
carboxylic acid + alcohol
ester + H O
2
conc. H SO
2 4
C
R
O
O R
ESTER
Reactions
hydrolysis
ester + H O
2
carboxylic acid + alcohol
reverse of esterification
ester + alkaline
salt + alcohol
reflux
reflux
HCl / H SO
2 4
2 2 2 2
F/Cl/Br/I
2 2 2 2
2 2 2 2
2
diol
diol
(iv)
OH
-
OH
-
OH
-
H
+
H
+
H
+
ketonnes/
carboxylic acids
2 2 2 2
order
1 <2 <3
O O O
O
(cloudiness)
(cloudiness)
hot
acidified
Reactions
dehydrohalogenation
halo-alkane
alkene + HX
halo-alkane + OH
alcohol
alcoholic alkaline
reflux with
nucleophilic substitution
-
halo-alkane + metal
gridnard reagent
gridnard
ether
organometallic compound
R
X
Mg
Full transcript