haloalkanes rxns 1 Flashcards
nuclear halogenation
an. Al Cl3
sandmayers reaction and diazolization rxn
- HCl ( 273-278K)
- CuCl2/ HCl
iodo benzene
shake the diazonium salt with KI solution.
- warm
fluorobenzene ( balz- Schiemann rxn)
fluoroboric acid
Gatter mann’s rxn
Cu powder and HCl
substitution by hydroxyl group
RX + KOH (aq)/AgOH
Substitution by Cyano group
- KCN is ionic and forms strong C-C bonds
- AgCN, covalent bond, C is attatched to Ag so only N is free and forms isocyanide.
RX + KCNalc) –> (good method)
RX + AgCN
3 rxns with CH3CN
- KCN
- H+/H2O
H+/NaOH
LiAlH4
Mendius rxn
CH3CN + H2 –> Ch3-Ch2-NH2
(Na and C2H5OH)
Hoffman’s amoolysis rxn
substitution by NO2 group
Ch3-ch3-br + AgNO2 –>Ch3-ch2-No2 + AgBr
Ch3-Ch2-Br + KNo2 –> Ch2-Ch2-ONO + KBr
Substitution by ester group
CH3-C=o (O0 Ag + X-R –> Ch3-C=O (O) R
- C2H5OH
beta elimination
rxn with metals
RX + Mg –>
RX + Mg –> R- Mg-X
dry ether
wurtz rxn
reduction
H2 Pt/Pd/Ni
Zu/Cu couple 2[H]
Red phosphorous 420K
Rearrangement rxn
an. AlCl3
dow’s process
chlorobenzene + NaOH –(663K, 300atm)–> Ona benzene —> dil HCL phenol +NaCl
substitution by NH2 grp benzene
clorobenzene + 2NH3 –Cu2O , 475K, 60atm–> 2aniline + Cu2Cl2 + H2O
Substitution by CN group
chlorobenzene + CuCN -(pyridine, 475K–> CN benzene
methods to prep alkyl chlorides
- HCl & ZnCl2
- PCl5
- PCl3
- SOCl2
prep alkyl chlorides
from alkanes
h neu
prep alkyl chlorides
from alkenes
markonikoff’s rule
prep vicinal alkyl dichlorides
from alkenes
Cl2 + CCl4
Finkelstein rxn
RX + NaI –>RI + NaX
dry acetone and reflux
Swartz rxn
RX + Hg2F2 –> RF + HgX
- CoF2, SbF3, AgF
Hunsdieker rxn
CH2COOAg + Br2 –> CH3Br + AgBr + CO2
CCl4
and heat
CN rxns 3 rxns
- Partial Conc. HCl (CONH2)
- complete dil.HCl (COOH)
- Red LiAlH4 (CH3-NH2)
Rxn with active metals
Mg
dry ether
wurtz rxn
wurtz fitting rxn
fittig rxn
wilmann rxn
cu
heat
reduction
2H
Ni-Al
NaOH