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H2SO4
+ HNO3 (HONO2) + H2O
Appendix 1
NO2
CH3 CH3
⎯ COO– + H+ ⎯ COOH
2 Appendix
Aliphatic primary – NH2 Add sodium nitrite (NaNO2), followed by dilute hydrochloric
amines acid, then warm:
C2H5NH2 Effervescence occurs
ethylamine NaNO2/HCl
RNH2 + O = N – OH ⎯⎯⎯⎯⎯→ ROH + N2 + H2O
(HNO2)
nitrous acid
Br
Br
Appendix 3
Aldehyde (RCHO) and (a) Silver mirror test: Aldehyde: Silver mirror formed
ketone (RCOR') Add Tollens’ Ketone: No reaction
reagent, then
warm
CH3COONH4 and CH3CONH2 Add FeCl3 solution CH3COONH4: Dark red colouration due
to formation of
(CH3COO)3Fe
CH3CONH2: No visible reaction
4 Appendix
CH3CH2Br and CH3CH2Cl Add silver nitrate in CH3CH2Br: Yellow precipitate formed
ethanol and warm CH3CH2Cl: White precipitate formed
CH3C6H4OH and C6H5CH2OH (a) Bromine water CH3C6H4OH: Decolourisation and white
precipitate formed
C6H5CH2OH: No reaction
C6H5CHO and C6H5COCH3 Add Tollens’ reagent, C6H5CHO: Silver mirror formed
then warm C6H5COCH3: No reaction
Comment Fehling’s
solution cannot be
used, as C6H5CHO
has no effect on
Fehling’s solution
CH3C6H4NH2 (or C6H5NH2) and Add bromine water CH3C6H4NH2 (or C6H5NH2): Bromine
C6H5CH2NH2 decolourised and white precipitate formed
C6H5CH2NH2: No reaction
Appendix 5
Cyclohexene and benzene (a) Br2 in CCl4 (or Cyclohexene: Bromine decolourised
bromine water) Benzene: No reaction
C6H5CHO and CH3COCH3 (a) Add Tollens’ C6H5CHO: Silver mirror formed
reagent, then CH3COCH3: No reaction
warm
CH3COOH and C6H5OH (a) Na2CO3 solution CH3COOH: Effervescence; CO2 liberated
at room C6H5OH: No reaction
temperature
C6H5CONH2 and C2H5NH2 Add NaOH(aq) and C6H5CONH2: Ammonia gas liberated
heat C2H5NH2: No reaction
6 Appendix
O
4
OH
2
H
SO
LiAlH4 COOH
Br 2
+
H
H2SO4
0
3
H2,Ni
0°
30
/H
20 atm
4
200 °C OCOCH3
C2H5HSO4 C2H5ONa
SO
O4
2
H 2S COOH
H
CH2 CH3COOH
O O2/Ag C
CH3COOH
180 °
HN
CH2 C2H4 , C2H5OH
NaOH, reflux
SO 4 aspirin
NaOH, reflux
250 °C
HX
O2
H2
OH 5
C
4
H
P/I2 C2H5OH
2
0°
H2O
C
OH
nO
CH3COOC2H5 CH3CN CH3OH CH3I CH3COOC2H5
14
5
H
NaOH
KM
/C
CH2OH KCN
Na
alc. reflux
CH2OH NH3 Li
C2H5OC2H5 C2H5X C2H5NH2 CH3Li
ether
H+
KCN alloy Na/Pb
alcohol O K2Cr2O7/H+ (CH3)3Pb
+ H– heat
N
K2Cr2O7/H
a/
Na/C2H5OH C2H5NH3+
Pb
C2H5CH2NH2 C2H5CN C2H5MgX
Mg
HS Grignard
2 O ether
HNO2 4 reagent
COOH
refl
COOH K2Cr2O7/H+ ux
CH3CH2COOH HCHO
C2H5CH2OH CH3CH2CHO
COOH LiAlH4
H2SO4 Cr2O72–/H+
KMnO4/H+ (CH3CH2)4Pb
180 °C HCHO R
R’ C O
HOOC
Br2 H2SO4 +
HCOOH acid RCHO
CO2 + H2O CH3CH=CH2 CH3CHBrCH2Br CO + H2O
heat +
H C2H5CH2OH acid R
Terylene r 2 SO
R ’ C—OH
HB H 4 MnO4–/H+
2O C2H5
Routes for the synthesis of aliphatic compounds
R
NaOH K2Cr2O7 CHOH
CH3CHBrCH3 CH3CH(OH)CH3 CH3COCH3 CO2 + H2O C2H5
reflux H2SO4
Appendix
7
11/13/08 12:36:38 PM
8
Appendix
OH
APPENDIX
CH3
CrO2Cl2 LiAlH4 HNO3
CHO —CH2OH HOOC(CH2)4COOH
KMn nO
O4 /H + 4 /H + Cl
O LiAlH4 K2Cr2O7/H+
NH2(CH2)6NH2
C—CH3
H2, Ni
15
O H, COOH 200 °C
C 2H 5O
Na
nylon
atm
eat
Cl
C—OC2H5 H C l, h
CH3Cl/AlCl3
OH
CO
, 30
3
COCl, NaOH O
20
,N
i
0
CH
0 °C
H 2 °C
OH heat C—O
H O—OH
250 °C, 25 atm, H3PO4 O2, 120 °C H2SO4
C—CH3 C—CH3 + CH3COCH3 NaOH (aq)
CH3CH=CH2 100 °C reflux
CH3 CH3
e
2 5
H
,F
cumene
0
4
2
Cl
C 2 °C,
4
l3
—N 2
+
Cl
/A 0 at
H H CO2Na + O–Na+
lC m
Fe2O3 polymerisation
C2H5 CH=CH2 —C—C—
( )n
600 °C N=N OH
H
55 °C
u.v.
HNO3/H2SO4
2
Cl ,
NO2 OH
NH2 N2+Cl– OH Br Br
Sn/HCl HNO2 H2O Br2
5 °C 70 °C
l H
2, N
Cl HC 20 Br
Cl Cl CH3COCl OH 0° i
OH O
C
NH3+Cl– NHCOCH3 K2Cr2O7/H+
Cl Cl
Routes for the synthesis of aromatic compounds
Cl N=N OH heat
11/13/08 12:36:38 PM
APPENDIX 5 Reactions of bromine with organic compounds
Br
+ Br2
Br
H – C ≡ C – H + 2Br2 → CHBr2CHBr2
– OH + 3Br2 + 3HBr
Br
NH2
Br Br
Br
+ 2Br2 + + 2HBr
Br
Appendix 9
As a strong acid Carboxylate Strong acid displaces weaker acid from its salt
RCOONa + H – HSO4 → RCOOH + NaHSO4
As a dehydrating agent Methanoic acid and Concentrated H2SO4 removes water molecules
ethanedioic acid from HCOOH and H2C2O4 (ethanedioic acid) or
their salts on heating
H2SO4
HCOOH ⎯⎯→ CO + H2O
H2SO4
H2C2O4 ⎯⎯→ CO + CO2 + H2O
10 Appendix
benzoate ion
ethylbenzene
Appendix 11