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Haloalkanes & Haloarenes Handbook
Haloalkanes & Haloarenes Handbook
Haloalkanes & Haloarenes Handbook
7 Chemistry HandBook
HALOALKANE
HC-CH-OH PCL NaBr+HS0, H,C-CHOH
3 H,C-CH2-OH PCl HI
KI/HPO, H,C-CH-OH
3 H,C-CH-OH Red P Br NBS
CCL HC-CH-CH2
H,C-CH-OH SOCl CH-X ClL/hv
alyfic substitu bon)
SOCl2
CH,-CH-x CH-CH,
H,C-CH-OH R-X HBr
SN X-FCI, Br, ) CC CHCH,
H,C-COAg Nal
CC. H,C-CH5-CI
Hunsdiecker Reaction) Acetone (Finkelstein Reaction)
H,C-CHOH HC/ZnClL
Lucas Reagent AgF or HgF, H,C-CH-CI
(Swart reaction)
Br HBr
Peroxide
HBr Br
HC-CH-CH, CC HC-CH-CH
Br Br,/800K HCI C
CH CHCH, HC-CH=CH2 H,c-CH-CH,
Br NBS
Br/CC, H,C-ÇH-CHBr
CHCHCH, CCl Br
Nucleophilic substitution
S1 3>2>1 CH-X (Reactivity order)
(R>R-Br>R-a>R-
S,2 1>2>3 CH-CHX Ambident NucdeophideN. õ-N=O
p*******aannsn* ************ R-X
(X=FCI, Br, )
*****s*a*************************sasa
HC-CH-1 N
-aron H,C-CH CHCH3
reacuon
Et,O
O
Aq KOH
HC-CHOH
HC-CHCH CH4 GHCli
Corey house synthesis
Moist AsOO
HC-CH-NH2 WAurtz-itug
Reaction
H Na/EtO
RCN
EOH HC-CHCEN
AgCN
H,c-CH-CEC-HH-CE N CH, MgBr Mg/EO HC-CH NET
AHF0 KO N-O HC-CHO-N=Op
HC-CH-H Alc. KOH
(1,2 not 3R-X) HC=CH
NaBH/EOH->2°& 3not 1 R--X AgON-O HC-CH;N
HC-CH-SH
HC-HN NaNO,
DMF
CH-CH
FC. Alkylatin
H-O-CH ******i H,C-CH-S-CH CHSNa
R-Br>19 CH-CHONE
RMgX R-R
RCOOCH
PHYSICAL PROPERTIES (3)Boiling point R-I>R-Br>R-CDR-F|
: (4) Density:
n-CH,Ckn-CH,Br<n-C,HI
(1)Dipole moment CH-Cl>CH,-F>CH,-Br>CH Y Br
(5) Solubility >
sligthly soluble in water
147
Chemistry HandBook
CHAPTER
ALLEN
TRI-HALO ALKANE
OH O O-C +HC
CI,+NaOH Light
CH-&R or H,C-H-H or NaOCl Cl
(Haloform test)
O
HNO Cl,C-NO2
CaOCl2
(Chloropicrin) (tear gas)
HC-C-CH Beachtng powder
Fe/HCI NaOH
CCl OH
Reimer Tiemann
reaction
HALO-ARENE
CI
Conc. HNO+ Conc. HSO, Ci/FeCl CI
NO, (ESR)
(ESR)
NO Cl
Ph
HC Ph-Br
CH,CI
AlCl (ESR) Na/Et,O
Fitlg Reaction
CH
CHBr
HC- Cl Na/Et,O O
Wurtz-Fittig Reaction
AlCl3 (ESR
oCH NH,
NaNH
C-C=o NH3
CCN O Conc. H,SOP
(ESR) ArSN
DDT OH
(Dichloro diphenyl trichloro ethane) (1) NaOI 1. 623K, 300 atm
(2) H
Ni-Al
NaOH
Conc. HSO,
ON NO2H.O O,N Q-HNO,|
SOH (ESR) warm
NO2
NO
So.H
NO NO CI
148
ALLEN CHAPTER
Chemistry HandBook
GRIGNARD REAGENT
REACTION
GRIGNARD REAGENT as Nucleophile
0-H Hc-C-H
(2) R-CH-CH R-C-CI OH
H,0 RMgX in excess/ H,0 R-C-R
R
0-H R-C-R
R-C-R R-CEN
R--R
R
HO H,0
H-C-R
H-C-OEt OH
leq.
HO R-CH-CH
OH OMgBr RMgBr -
R-CH-R H-C-R H-C-OEt R-CH-CH,
R
RMgX in excess RMgK itH,0 R-CH-CHR
R-C-OEt
R-C-R R-O-H
leq..RMgX H,0
-OEt
0-H Q-H
R-C-R OEt Cl-C-C
R H0 RMgX in excess /H0+ R-C-R
R
eRMgx
q Cl-CEN
R-CEN+MgaBr
R-C-C Cl-C-CI
149