Preparation of Alkyl Halides Reaction

CH3CH = CH3 + H — I CH3CH2CH2I + CH3CHICH

001
minor major

H H
CCl4
002 C = C + Br2 BrCH2 — CH2Br
H H

R — X + NaI R — I + NaX Finkelstein

003
Reaction
X = Cl, Br

AgF, Hg2F2, CoF2 or SbF3 Swarts

004 H3C — Br CH3 — F + AgBr Reaction
Nucleophilic Substitution of Alkyl Halides Reaction
Ag — C ≡≡ N R — N ≡≡ C
Isocyanide
R — OH, reaction is known HOH or
as hydrolysis NaOH/HOH

AgNO2 O
R — O — N == O + R — N
R—O—R R’ — O 005 016 O
Ether NaOH/HOH 015
006
NaO — N == O R — O — N == O
Alkyl halide should only be primary because 014 Alkyl Nitrite
secondary and tertiary alkyl halides undergo
dehydrohalogenation in the presence of 007 R—X
R — O which is strong base for elimination 013 N3Na R — N3
reaction.
Alkyl Azide
008 012
R—S—H NaSH
Thioalcohol 009 011 R’
010 R3N
R—N R’ X
R’
R—S—R Na2S
Thioalcohol R’ — C ≡ CNa
O
reaction is SN2 only O
R’ — C — ONa
R—C≡N NaCN or KCN R — C ≡≡ C — R’ R — O — C — R’
Cyanide Alkyne Ester
Nucleophilic Substitution of Alkyl Halides Reaction

Cl OH
Dry ether NO2 NO2
CH3CH2Br + Mg CH3CH2MgBr (i) NaOH, 368K
017 021
Grignard reagent (ii) H

NO2 NO2

018 RMgX + H2O RH + Mg(OH)X

Cl OH
O 2N NO2 O 2N NO2
warm
022
H2O
Cl OH
019 NO2 NO2
(i) NaOH, 623K, 300 atm
(ii) H

X R
Dry ether
023 + Na + RX + 2NaX
Cl OH

(i) NaOH, 443K

020
(ii) H
X
Dry ether
NO2 NO2 024 2 + 2Na + 2NaX

Diphenyl