X?
R-R ? R?X ? H?X (alkane)
alkyne ? quadruple substituted alkane
HX
alkene? substituted alkane
alkyne? substituted alkane
epoxide ? CX-COH ? CX-CX
X?
alkene? double substituted alkane
alkyne? double substituted alkane
NBS
allylic H? allylic Br
HX, PX?, or others
R?OH ? R?X
acetone and I?
R-X ? R-I and X?
18-crown-6 and CH?CN and KF
R-Cl ? R-F
?OH
R-X ? R-OH ? X
RO? or RS?
R-X ? R-O-R or R-S-R and X?
excess NH?
R-X ? R-NH?
-C?N
R-X ? R-C?N and X-
KOH
CH-CX ? C=C + X-
base, heat (loss of HX)
HC-CX ? C=C
NaI and acetone
CBr-CBr ? C=C
conc. H?SO? or H?PO? and heat
CH-COH ? C=C and H?O
heat, catalyst
CH-CH ? C=C
Ag?O, heat
CH-CN(CH?)? ? C=C (usually most substituted alkene)
H?, Pd/BaSO? and quinoline
C?C ? C=C (cis)
Na, NH?
C?C ? C=C (trans)
H?O and H+
C=C ? CH-COH
Hg(OAc)? and H?O then NaBH?
C=C ? COH-CH (markovnikov)
Hg(OAc)? and ROH then NaBH?
C=C ? COR-CH (markovnikov)
fused KOH
CX-CX ? C?C
NaNH?
CH-CX? ? C?C
NaNH? or R'Li or R'MgX
R-C?C-H ? R-C?C? +Na or R-C?CLi or R-C?CMgX
Pt, Pd, or Ni and 2H?
C?C ? C-C
HgSO?, H?SO?
C?C ? ketone
(1) Sia?BH * THF (2) H?O?, NaOH
C?C ? aldehyde
KMnO? and H?O, neutral
C?C ? R-C=O - C=O -R
(1) KMnO?, -OH (2)H+ (or O?, then H?O)
C?C ? 2 carboxlic acids
NABH?
aldehyde or ketone ? alcohols
LiAlH?
acid anion or ester ? alcohol
(1) ether and R-MgX (2) H?O+
C=O ? R-C-OH
Raney Ni and H?
C=O ? CH-OH
Na?Cr?O?, H?SO?
CH-OH ? C=O
PCC
R-CH?-OH ? R-C=O -H
(1) TsCl / pyridine (2) LiAlH?
R-OH ? R-H
HCl or SOCl?/ pyridine
R-OH ? R-Cl
HBr or PBr?
R-OH ? R-Br
HI or P/I?
R-OH ? R-I
H?SO? or H?PO?
CH-COH ? C=C
2 R-OH and H+
2R-OH ? R-O-R and H?O
R-OH and TsCL and pyridine
alkyl tosylate and H-CL
R-OH and acyl chloride
R-OH ? ester
R-O and R'X
R-O ? R-O-R
epoxide + H+ and H?O
epoxide ? COH-COH
epoxide + H+ and R-OH
epoxide ? COH-COR
expoxide and R-O and R-OH
epoxide ? COH-CH?-OR
R-(MgX or Li) and then H?O+
epoxide ? COH-CH?-R