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Organic Reaction Map
1
2˚ only: Cr 2 O 7 2- , H + , refux ORGANIC FUNCTIONAL GROUP INTERCONVERSIONS ESTER ALKANE ALKENE ALCOHOL HALOALKANE ALDEHYDE KETONE CARBOXYLIC ACID ETHER AMIDE AMINE NITRILE ACYL CHLORIDE EPOXIDE ALKYL HYDROGENSULFATE REACTIONS KEY ADDITION SUBSTITUTION OXIDATION REDUCTION ELIMINATION HYDROLYSIS ACYLATION ESTERIFICATION Halogen & UV light ADDITION POLYMER ACID ANHYDRIDE Cracking (variety of products) Polymerisation H 2 , Ni cat., 150˚C, 5 atm Hydrogen halide (aq), room temperature Hot, conc. KOH, alcoholic solution Conc. H 2 SO 4 H 2 O, warm Steam, 300˚C, 60 atm, conc. H 3 PO 4 cat. O 2 , Ag cat., 250-300˚C, 10-20 atm (ethene only); other alkenes: RCO 3 H in CH 2 Cl 2 Al 2 O 3 , 300˚C, or conc. H 2 SO 4 , refux NaOH (aq), refux KCN, ethanolic solution, refux Conc. NH 3 , heat in sealed tube H 2 SO 4 , heat (1 ˚ alcohols only) 1 ˚ only: Cr 2 O 7 2- , H + , distil NaBH 4 , alcoholic or alkaline aq. solution, heat; or LiAlH 4 in dry ether NaBH 4 (aq, heat) or LiAlH 4 (ether) Cr 2 O 7 2- , H + , refux 1 ˚ only: Cr 2 O 7 2- , H + , refux OTHER H 2 O & acid/base catalyst P 2 O 5 , distil LiAlH 4 (ether) H 2 SO 4 & heat P 2 O 5 , distil H 2 O, refux ROH, conc. H 2 SO 4 cat. Refux, H + or OH - ROH (anhydrous), refux NH 3 , refux (gives 1 ˚ amide); RNH 2 , refux (gives 2˚ amide) SOCl 2 , PCl 3 or PCl 5 , refux H 2 O Conc. NH 3 , room temp. (gives 1 ˚ amide) RNH 2 , refux (gives 2˚ amide) ROH, room temp. H + (aq), H 2 O, refux LiAlH 4 in dry ether LiAlH 4 (ether) R X R 1 C C R 2 H H H H C C R 2 R 4 R 1 R 3 R OH R C N R NH 2 O R 1 R 2 O C C R 1 R 2 R 3 R 4 O C R H O C R 1 R 2 O C R OH O C R 1 OR 2 O C R NH 2 R C O Cl O C R 1 O C R 2 O C C R 2 H OSO 3 H H H R 1 BY NC ND © COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COM Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. C
description
Organic chem
Transcript of Organic Reaction Map
-
2 only: Cr2O72-, H+, ref ux
ORGANIC FUNCTIONAL GROUP INTERCONVERSIONS
ESTER
ALKANE ALKENE
ALCOHOL
HALOALKANE
ALDEHYDE
KETONE
CARBOXYLIC ACID
ETHER
AMIDE
AMINE
NITRILE
ACYL CHLORIDE
EPOXIDE
ALKYL HYDROGENSULFATE
REACTIONS KEYADDITION
SUBSTITUTION
OXIDATION
REDUCTION
ELIMINATION
HYDROLYSIS
ACYLATION
ESTERIFICATION
Hal
ogen
& U
V lig
ht
ADDITION POLYMER
ACID ANHYDRIDE
Cracking (variety of products)
Polymerisation
H2, Ni cat., 150C, 5 atm
Hydrogen halide (aq), room temperature
Hot, conc. KOH, alcoholic solution Conc
. H2S
O4
H2O
, war
m
Stea
m, 3
00C
, 60
atm
, con
c. H
3PO
4 cat
.
O2, Ag cat., 250-300C, 10-20 atm (ethene only); other alkenes: RCO3H in CH2Cl2
Al2O
3, 30
0C,
or c
onc.
H2S
O4,
ref u
x
NaOH (aq), ref ux
KCN, ethanolic solution, ref ux
Conc. NH3, heat in sealed tube
H2SO4, heat (1 alcohols only)
1 only: Cr2O72-, H+, distil
NaBH4, alcoholic or alkaline aq. solution, heat; or LiAlH4 in dry ether
NaBH4 (aq, heat) or LiAlH4 (ether)
Cr2O72-, H+, ref ux
1 only: Cr2O72-, H+, ref ux
OTHER
H2O
& a
cid/
base
cat
alys
t
P 2O
5, di
stil
LiAlH4 (ether)
H2SO4 & heat
P 2O
5, di
stil
H2O
, ref
ux
ROH
, con
c. H
2SO
4 cat
.
Ref u
x, H
+ or O
H-
ROH
(anh
ydro
us),
ref u
x
NH3, ref ux (gives 1 amide); RNH2, ref ux (gives 2 amide)
SOCl2, PCl3 or PCl5, ref ux
H2O
Conc. NH3, room temp. (gives 1 amide)
RNH2, refux (gives 2 amide)
ROH, room temp.
H+ (aq), H2O, ref ux
LiAlH4 in dry ether
LiAl
H4 (
ethe
r)
R X
R1 C C R2
H
H
H
H
C CR2
R4
R1
R3
R OH
R C N
R NH2
OR1 R2
OC CR1 R2
R3 R4
O
CR H
O
CR1 R2
O
CR OH
O
CR1 OR2
O
CR NH2
RC
O
Cl
O
CR1 O
CR2
O
C C R2
H
OSO3HH
H
R1
BY NC ND
COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COMShared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence.
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