Grade 12
CONVERSION SCHEMES IN ORGANIC CHEMISTRY
SCHEME- I: Conversions related to alkyl halides
RCH:CHOH1° alcohol
HCHO
RCH:CH -OH| 2° alcohol
RCHO R'
Mg. ether
R-CH:MgBr COR. R-CH:-C R-OH 3° alcohol
R"
RCH:COOH|Carboxylic acid
RCH;CH:ci+ 2Na + CICH:CH,Ry elheRCH,CH:CHCH
Alkyl halide Alkane
alc. KOH Br: alc. KOH
RCH =CH: RCHBr-CH;Br -2KBr RC = CH
Alkene -2H:0 Alkyne
aq. KOH Cu573K
RCH:CH-OH H |RCH:CHO Aldelhyde
Alcohol
NH
-HCI
RCH:CH;NH:
KMn0, KMnO.
RCH,COOH| Carboxylic acid
Alkyl amine
Grade 12
SCHEME-II: Conversions related to aryl halides
NaOH dil. HCI
623 K. 300 atm -ONa -OH
Sod. phenoxide Phenol
O-a NH2 +CuzCh +H:0
2NH+Cu:0
Aryl amine
CuCN
Pyridine 475 K O-CN+CuBr
C'yanobenzene
Mg ether
O-MgBr
Phenyl magnesium
bromide
CI 2Li dry cther
O-i+LiBr
Phenyl lithium
Aryl halide C-CHst2Na (O-CH +2NaCI
Toluene
2H
+ 2HCI
Ni-Al NaOH
Benzene
Ch
CI
a +
o- dichlorobenzene p- dichlorobenzene
[Link],A
+ HSO,
SO.H
0- sulphonic acid p- sulphonic acid
kO-a+2Na
ONci
Diphenyl
Grade 12
SCHEME- II: Conversions related to aryl halides
NaOH -ONadil. HCI
623 K, 300 atm O-OH
Sod. phenoxide Phenol
2NH;+Cu:0 +2(ONH, +Cu:Ck +H0
Aryl amine
CuCN
Pyridine 475 K O-CN+CaBr
Cyanobenzene
Mg ether
MgBr
Phenyl magnesium
bromide
CI 2Li dry cther
O-i+LiBr
Phenyl lithium
Aryl halide |Cl-CHst2Na
KO-CH +2NaCl
Toluene
2H
+ 2HCI
Ni-Al NaOH
Benzene
Cl
CI
o- dichlorobenzene p- dichlorobenzene
H:SO,A
SO;H
+ HSO,-O-c1
0- sulphonic acid p- sulphonic acid
KO-Ci+2Na
+2NaCI
Diphenyl
Grade 12
SCHEME - III: Conversions related to alcohols
conc. H;SO/A HyNi
RCH, -CH,OH
-H;0
RCH =CH: RCH,-CH
Alcohol Alkene Alkane
Br:
PCls
RCH;-CH:C1|Alkyl RCHBr CH;Br
Jhalide
-HCL NH ale. KOH
RCH:CH-NH: RC = CH
Alkyl amine
Cu/573K KMnO4
RCH:CHO RCH,COOH
H or
Aldelhyde K:Cr.O Carboxylic acid
KMnO
RCH,COOHCarboxylic acid
NH(vap)/A/ALO,
RCH:CH:NH:
Alkyl amine
Grade 12
SCHEME-IV: Conversion related to phenols - I
2Na
O-ONa+ H:
Sod. phenoxide
NaOH
-ONa+ H:O
Sod. phenoxide
Zn
+ZnO
Benzene
NH
Anhyd. ZnClh. O-NH; +H.0
675 K Aniline
CH:COCl or
(CH:CO):0 AICh,A
Pyridine (O-ococH: OH
COCHs
+ [Link]-KO-OH
OH - HCI
o- phenyl acetate p- phenyl acetate
Br: in CS:
OH + Br-<O -OH
Phenol Br
o- bromo phenol p- bromo phenol
B
3Br:
Br -OH+ 3HBr
Br
2,4, 6-tribromophenol
Dil. HNO,
O-oH
NO,
+NO,O-oH
o- nitrophenol p- nitrophenol
Conc. HSO
288- 293K O-oH SO.H
2- hydroxy benzene
sulphonic acid
Conc. H;SO
373 K HSO, OH
4- hydroxy benzene
sulphonic acid
Grade 12
SCHEME- V: Conversion related to phenols -II
Conc. HNO, + NO
H:SO:
+NO; KO-OH+
NO
H:0
2,4, 6- trinitrophenol
(Picric acid)
CH:CI
Anhyd. AlICl, -OH + H:C<O-OH
CHs
o- cresol p- cresol
NaOH (CH:CO),o
CO:, 4-7atm
Kolbe's rcaction
-OoH
COOH Conc. H;SO
O-ocoCH+CH:COOH
COOH
Salicylic acid Aspirin
3H,,Ni
O-oH
Cyclohexanol
OH
CrOs 0+H0
p- benzoquinone
CHCL,NaOH
340 K HCI
Phenol -OH
Reimer Tiemann
reaction CHO
Salicylaldehyde
CCl,NaOH
340 K HCI
Reimer Tiemann
rcaction
COOH
Salicylic acid
FeCly
Fe+ 3HCI
Ferric phenoxide
[Link]
NaOH O-N=N-O-oH -HCI
p- Hydroxy azobenzene
Grade 12
SCHEME- VI: Conversion related to aldehydes
Clemmensen Reduction
RCH;CHO RCH;-CH:
Zn (Hg) + HCI
Aldehyde or Alkane
Wolfr Kishner Reduction
NH- NH;+ KOH + glycol
conc.H;SO.
H/Ni
RCH, -CH;OH| RCH -CH Alkane
Alcohol Br:
PCls
+RCHBr-CH;Br
KMnO
RCH,COOH RCH:CH:C Alkyl alc. KOH
halide
-HCI NH3 RC = CH
Alkyne
RCH:CH;NHAlkyne amine
Grade 12
SCHEME- VI: Conversion related to carboxylic acids
PCk or PCh or SOCh
RCH; COOH RCH; COCI Acid chloride
Carboxylic acid NH
NHS
RCH; CONH: Acid amide
ROH
Conc. H:SO,
RCH:COOR'
Ester
Bre/KOH
Hoffinann
Bromamide
reaction
CaO +NaOHA RCH;CH, RCH: NH:
Alkanc Amine
LiAIH, or BaH6
RCH; CH, OH
Alcohol
Clemmensen Reduction
Zn(Hg) + HCI
Or
RCH;CH,
Wolff Kishner Reduction Alkane
NH,- NH, + KOH + glycol
Or
HI/Red P
NH/Ni RCH; CHO
Quinoline
Aldehyde
Grade 12
SCHEME VII: Conversion related to alkyl amines
4RI
RCH; NH RCH;NI
Aminc Tetra alkevl
ammonium
iodide
R'COCI RCH; NHCOR'
Amide
R-C-0-C-R R'COOH
+RCH:NH-C-R'
Acid amide Carboxylic acid
CI
RCH,NH-C<0)
Amide
RCHO
RCH= NR'
Schiffs base
CHCh+ 3KOH(ale.)
RCH; NC+3KCI+ 3H:0
Carbylamine reaction
Isocyanide
HNO:
RCH; OH
Alocohol
S=C=S/A HgClh
RCH;NH-C-SH
Heat
RCH;-N=C=s
Dithioalkyl carbamic Alkyl
acid isothiocyanate
R-CH:-NH-C-NH-CH:-R
Symm. disubstituted arca
[o] RCHNHOH
[o] +R-CH, NO:
alk. KMnO.
Hydroxyl Nitroso Notro compound
amine compound
Grade 12
SCHEME - VII: Conversion related to aryl amines
Ho/A
|ArOH| Phenol
CuCN
Ar-CN Cyanobenzene
KI,A
|Ar I lodobenzene
HBF4
Ar F Fluorobenzene
CuBr
NaNO, + HCI Ar Br Bromobenzene
ArNH2
0-5°C
ArN Ci Cu:Ch ºAr C1 Chlorobenzene
Aryl Diazonium
amine Chloride HBF Ar-NO. Nitrobenzene
NaNO
HiPO:,H:Ar- HBenzene
OR
O-N=N-O-R'
Azodye
NaSH
| Ar- SH Thiophenol
ASCENDING SERIES
(1) By Wurtz Reaction
Dry cther
R-X+ 2Na + X -R R-R+ 2NaX
R-X+ 2Na +X-R' Dry cther R-R'+ 2NaX
(2) By Using Cyanide
Grade 12
Red P+I; KCN
RI
Na in C;[Link]
ROH HNO RCH,NH: (Reduction)
REN
(Reduction)| HNi
HNi RCOOH HOH RCONH
RCHO Reduction)
(3) By using Grignard's Reagent
OMgX OH
HCHO HH:0
H-Ç-H H-C-H (1° alcohol)
MgXOH
R R
OMgX OH
RCHO HHO
RMgX R-C-H (2° alcohol)
MgXOH
R
OMgX OH
R--R" R-C-R"
HH0
(3° alcohol)
MgXOH
R
(4) By using Sodium Alkylnides
R-X+ NaC=C-R +R-C=C-R+ NaX
This reaction is used for terminal alkynes.
Grade 12
DESCENT OF SERIES
(1) Hoffmann Bromamide reaction
HNO: alkalinc KMnO.
RCH-OH
[O]
RCH;NH2 RCOOH
Br/KOH NHVA
RCONH:
Hoffmann
bromamide degradation
(2) Decarboxylation reaction
CL/hu aq. KOH
+RCH;CI RCH;OH
RCH; alkaline KMnO4
RH [O]
CaO + NaOH NaOH
-RCOONa -RCOOH
