MOC Alcohol RXN Map PDF
MOC Alcohol RXN Map PDF
MOC Alcohol RXN Map PDF
Conditions
Cl2, h
Br 2, h
Elimination [E2]
RO /ROH
Elimination [E1]
polar solvent,
heat
Reaction
Reaction Map: Reactions of Alkanes, Alkyl Halides, Alkenes, Alkynes and Alcohols
56
Alkenyl halides
X
H
R
Vicinal
Dihalides
X
X
Geminal
Dihalides
X
X
R
51
50
54
55
55
23
21
53
24
20
52
Alkenyl dihalides
Epoxides
O
27
47
28
39
R C C R
40
29
42
38
15
30
44
10
SR
11
12
N3
13
CN
14
15
HCl
65
16
HBr
Thiols
17
HI
18
HBr, h
19
Hydrogenation of alkenes
Pd/C, H 2
syn- selective
20
Alkene chlorination
Cl2, CCl4
anti- selective
21
Alkene bromination
Br 2, CCl4
anti- selective
22
Alkene iodination
I 2, CCl4
anti- selective
23
Chlorohydrin formation
Cl2, H 2O
Br 2, H 2O
Ring opened
products
HO
60
58
18
68
67
Nu
Disulfides
R S S R
61
"Carbonyls"
66
62
O
O
SH
R OH
17
HO
ROH
RCO 2
in
polar
aprotic
solvent
Alcohols
16
31
19
43
Tetrahalides
X
X
X
X
R
R
37
R OR
59
36
H 2O
46
45
35
Ethers
34
OH / H 2O
69
25
Alkenes
Alkynes
26
32
41
47
OH
22
48
Cyclopropanes
33
49
HO
57
Vicinal Diols
Halohydrins
HO
X
Name
O
4
Alkanes
RH
63
64
R SH
1
2
Alkyl Halides
10
RX
R C C
14
Alkyl Sulfonates
This "map" includes reactions typically covered in chapters covering:
Substitution and eliimination reactions of alkyl halides
Reactions of alkenes
Reactions of alkynes
Free-radical substitution of alkanes
Alcohols and thiols
10
11
13
12
Sulfides
["Thioethers"]
R SR
ROTs
ROMs
or NCS
Esters
Nitriles
R C N
Azides
R N3
O
R O
R
24
Bromohydrin formation
or NBS
25
Iodohydrin formation
Cl2, H 2O
or NIS
26
Epoxidation of alkenes
27
Dihydroxylation of alkenes
with OsO 4
RCO 3H
(e.g. m-CPBA)
OsO 4, KHSO 3
(e.g. m-CPBA)
syn- selective. Important to keep cold,
otherwise oxidative cleavage occurs (see 31)
28
Dihydroxylation of alkenes
(cold KMnO 4)
KMnO 4, NaOH
(cold, dilute)
29
Ozonolysis (reductive
workup)
30
Ozonolysis (oxidative
workup)
O 3, then H 2O 2
31
KMnO 4, acid,
heat
32
Cyclopropanation (SimmonsSmith)
Cu/Zn, CH2I 2
syn-selective
33
Dichlorocyclopropanation
CHCl3, KOH
syn-selective
56
NaH (strong
base)
57
H 3O+ (or
H 2O/H 2SO4 )
58
Elimination of alcohols to
form alkenes (acidic)
H 2SO4, heat
59
POCl 3 elimination of
alcohols to alkenes
POCl 3,
pyridine
E2 reaction
34
Acid-catalyzed ether
formation
H 2SO4, ROH
35
Oxymercuration
Hg(OAc) 2, ROH,
then NaBH 4
36
Oxymercuration
Hg(OAc) 2, H 2O,
then NaBH 4
60
HI, heat
37
Hydroboration
BH 3, then NaOH,
H 2O 2
61
Conversion of alcohols to
alkyl halides with PBr 3
PBr 3
38
Acid-catalyzed hydration
H 2SO4, H 2O
("H3O+")
62
SOCl2 conversion of
alcohols to alkyl chlorides
SOCl2
39
Partial hydrogenation
(Lindlar)
Lindlar, H 2
syn-selective
63
HCl, HBr, HI
40
Partial hydrogenation
(sodium reduction)
Na/NH 3
anti-selective
Alkyne hydroboration
BH 3, then NaOH,
H 2O 2
64
TsCl or MsCl
41
42
Alkyne Oxymercuration
HgSO 4, H 2O,
H 2SO4
65
Disulfide formation
I 2 (oxidant)
43
Alkyne Ozonolysis
O3
66
PCC
44
KMnO 4, H +
same as ozonolysis
67
K 2Cr2O 7 +
acid
45
Hydrogenation
Pd/C, H 2
68
Dess Martin
Periodinane
46
Cl2, Br 2, or I 2
(2 equiv)
69
Grignards,
OH, LiAlH
4
47
Halogenation
Cl2, Br 2, or I 2
(1 equiv)
anti-selective
48
HCl
Markovnikov selective
49
HBr
Markovnikov selective
50
Addition of HI to Alkynes
HI
Markovnikov selective
51
Addition of HX to
haloalkenes
HCl, HBr,
or HI
Markovnikov selective
52
HCl [2 equiv]
53
HBr [2 equiv]
54
Double addition of HI to
Alkynes
HI [2 equiv]
55
Elimination of dihalides to
give alkynes
NaNH 2 [2
equiv]