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All Organic Chemistry Reactions
Everything to know for each reaction —>
I. Alkenes
A. Carbocation Pathway
1.Addition of Halides (H-X)
i. Addition of HBr
ii. Addition of HCl
iii. Addition of HI
2.Acid Catalyzed Electrophilic Addition
i. Acid Catalyzed Addition of Water
ii. Acid Catalyzed Addition of Alcohol
iii. Acid Catalyzed Addition of Carboxylic Acid
3.Rearrangements
B. 3 Membered Ring Pathway
1.Halogen Addition
i. Bromination
a. In Presence of Water
b. In Presence of Alcohol
2.Oxymercuration-Reduction
i. With Alcohol As Solvent
C. Concerted Pathway
1.Hydroboration-Oxidation
2.1,2-Dihydroxylation
3.Catalytic Hydrogenation
D. Ozonolysis
II. Alkynes
A. Catalytic Hydrogenation
1.To Alkane
2.Lindlar
3.To (E) Alkene
B. C(sp)-C(sp3) bond formation
1.Alkynyl Anion Formation
2.SN2 with Alkyl Halide
C. Addition
1.Hydrohalogenation
2.Halogen Addition
3.Hydration
i. Acid Catalyzed
ii. Hydroboration-Oxidation
III. Ketones and Aldehydes
A. Enol-Keto Tautomerism
~
X
↑ ↑ (^) ~
~ ~ ~ ~ w ~ ~ ~ X ~ X
: Provides er (^) pair to^
form (^) new siralent (^) bond ,
Levis
Ben
: Accepts e pair to^ form new covalent^
bond ,
Lewis Acid
Addition of HBr
Hydrohalogenation
Hey
Bonds
Formed
Bonds
Broke
· C- Br
Summary
· C
· H-Br
3r
R
H
uBr
&egiozhem
Markornikov
Stereochem
Y
Che
Cl- A^
M
Alkene Alky1 Bromide
Mechanism
S Sa
Br
H-Br
&
3r e
I
V
H -^
X
electrophilic attack^
nucleophilic trepping
Examples Limitations
Addition
of (^) HL)" HE follow same^
process
Reactivity
decreases as atom size^ increases
MB r
HCl
HE
↑
Acid Catalyzed Addition of Alcohol
Akrhol Addition^
↓ y
Bonds foreed Bonds (^) Broke
0 · C
masO
in
a
no
· C
Ij
... (^) S R
Regrochem
: (^) Markovnikov Stereochen^
: Random
Altere
Ether
has CHOH CHOHr^
+ Hs0 + H- -Iz
H
--
or
W
i
↑
↑
H
jo
R
-z
↑
ja
x (^) -
1
R
I I
Exeples
limitations
·
Alcohol
must be (^) MePH
or a^10 alcohol
Acid Catalyzed Addition of
Carboxylic Acid
key
Bonds formed
Key
Bonds Broken^6
·^ ((n) (-
Summary
t
· C
· 0 -H
& 17
N (^) I'M
Reochem
: (^) Markownikov Stereochem^
: Random O
Alken z
↑ of Ester
ha CLOON
Cl00e
i ...
o
H &^ or
H- - - r
& (^) - O -
⑪
O H II &
I 1 H
⑪
↑
H
↑
jo
n
ja
I H H^ -
1 -z -
xp
R
I I
Examples (^) Limitations
⑭
Bromination in the Presence of Water
key
Bonds formed Key Bonds^
Broken BC
~ Halohydrin
formation
· C- OH^
Summary
H · C-Br
· Br-Br
R &
H
,
1
-H + HBr
n
L
on
R
R
Regiochem
:
Markovik
a Stereochen
: Anti
enant. -
Alter
Alcohol
Mechanism
B -Br
R
↑↓-
Bro an ↑ I^ -
H
=
-1) , L I^ H
↑= wi
, (^1519) H &^
I J^ It (^) R
I I > - O
/
(^7) -
I
H
I
R R & ↑^
enantiomer
j
-0H .
Br
H (^) I H Br or
can (^) attack
fr a H Br
↓
&
Exeples
Imitations
The more substituted bridged carbon holds more
partial positive^ change
Bromination in the Presence of Alcohol
key
Bonds formed Key Bonds^
Broken BC
~ Halohydrin
formation
· C- OH^
Summary
H · C-Br
· Br-Br
R &
Brz
R (^) O
,
1
-H + HBr
n
L
R ROH
Ver R
R Regiochem
:
Markovik
a Stereochen
: Anti
enant. -
Allane
Ether
Mechanism
B -Br
R
↑↓
Bro an
↑ I^
H
=
- I
- S^ -^ H^ Br -1) , L I^ H -- R
↑= wi
I
n
d
J (^) It
/ 7
I (^) H
R R & ↑^
enantiomer
j
-0H .
Br
H (^) I H
Br &
can (^) attack
fr a #1 (^) ↓
Exeples
Imitations
bridged carbon^ holds^ more
partial positive^ change
Oxymercuration-Demercuration in
Presence of Acid
H
Bonds formed
My
Bonds Broke^ d
Alcohol Addition
S
Summary 2 ↑
-Me
Et
I NS
D + -
/ (^) ROt
I
Regrochem
: (^) Markovnikov Stereochem : Random
Altern Ether
Mechanism
Same as^ last one
Exples
Imitati eul carboxylic
acid
,
or 3" alcohol
Hydroboration- Oxidation
Hydratin
H
Bonds formed
My
Bonds Broke^ d
S
Summary
↑
Do
o
↑
H
↑
XXOH
Regrochem
: (^) Anti-Markovnikov Stereochem : Syn (^) (M , OH)
Alkne Alcohol
Mechanism ro a
on
I-
R
For
&
i B
·
H
R
on
a
o
H
& (^) -
-L
↑ (^) -
41
I'
N
-- - (^) D
·
"A D
j
o
Hod H
M of
oh
&
C
I ,,,,
O I^
=
%
L. H on
H
tenut ↑
BR=OH
-/ D
....
Exeples
tenant
.
. Imitation
e on ester^ or^
an ether Can't
· Sturrs bulk^
: - Bu >^
C >
isopropyl
vcyclohexylsEt? Meph
· when staggered
: ·
poak
I substituents^ that were (^) APP on (^) the allee
· rotate
conforme so
thy
App
· Added (^) RzB" I groups
should be^ gauche
Catalytic Hydrogenation
of Alkene
↓ y
Bonds foreed Bonds^ Broke
S
Summary
2 ↑
T
FY
- PEO = (^) /metal catalyst
Regrochen
:
N/A
Stereochen : ~or solvent - Syn
Alkem Alkane
Mechanism
D Hz
:
: &
1 -
Y
Pd
m+al
Surface
Exeples
Limitations
C·
functional
group compatibility
- can be (^) in volecule w) akem
:
phenyl ,
ester ,
alcohol , anime ,
2-
· cannot be in
molecule :^
Ketore
, aldehyde ,
GBr ,
2-
· 2 metal
catalysts
: PtL Pd/(
·
solent
usually
Not
Ozonolysis
↓ y
Bonds foreed Bonds^ Broke
h
S
↑
2
E
-min
: Stereochen :
Alkana 2
ketores/aldehydes
Mechanism -^ - [ o ·...]
O O &^
o ⑦
=^0 v L ⑧ -Mu
=!^ / kyrl
G (^) 0-
I S
Mr
↑
↓
p
L -o^ ozonice
~
T
=
It
-See
Exeples Limitations
Catalytic Hydrogenation of Alkyne (Lindar’s Catalyst) H Bonds formed yBonds Brok a
S C
H mary · C-H
H - H (z)
Regrochen :
N/A
Stereochen :
Alkyne
Alkma
Mechanism
No
need to know
Exeples Limitations ·
functional
group compatibility
can be (^) in molecula · phenyl ,^ allow , ester ,
alcohol
, amive^ , latir , aldehych, (not altered) C-Cl , C-Br ·
Internal
alkyne
E alko · terminal
alkyne ->
terminal
allee
·
Lindlar's
Catalyst :
Ma/caci
,
Pb
,
quialime
([ITE)
Catalytic Hydrogenation of
Internal Alkyne to (E) Alkene
H
Bonds formed
May BondsBrother
partial
reduction
· C-H
Summary
· C-H
2
A
lig
. Nita Regiochem
: Not Stereochen :
Syn
Alkyne
All
(t)
Mechanism
&
Na atros in^ liquid (^) ammora Eject 12-^ that floats around^
in solution^
(very righ^
NRO i solvated (^) ef
largeRr
a trans is
eisolvated)
"
↑
sand
~
M
S " . Ye N- M "I
<^2 NaTOENty
H (^) Every strong base)
Exeples
Limitations
· (^) functional
grown
compatibility
:
can be^ in molecule (maltired)^
: allow
,
ethr
,
anive
can't be in mobenze(changed)
:
phenyl (^) ,
katire
, aldehych ,^ ester,
24
c -Br , C-E ,
allcohol
,
Thiol
(MSM)
, ferminal carbox
alkyne
SN2 with Alkyl Halides
- ((sp)-((sp3) bred formation^
H
Bonds formed
Bonds
Broke
l
o
· (^) L-C
Summary
2 ↑
Na
OE-R
(
-X (^) - R
Alky/Halide
Alkynyl
Alkyne
Regrochen
: Stereochen :
Anion
Mechanism
↑ :^
↑ A
d
--
Nach C^
+ + Brt^ Nat
S
-- L
Nu backside approach
Exeples
limitations
Requirements
:
- (^) Me or 102(sp3)- Br (^) or
<(sp2)
I-CH
In
Br- (^) CHz
Br3i
Bru
Br - E
C(sp)
No H-
,
H-s ,
H-
, c group
in electrophile
(pka224)
- exothermic (^) acd base rxn happens - 10
fold faster the^ L--bond
formation
Electrophilic Addition to Alkynes
H
Bonds formed
My
Bonds Broke d
S
Summary
= zegHr^
↑
2
M
T
A , Ch
Alkene
unreacted
Rochen
: Markovikov
Stereochem : Random
Alkym Alkase^ alkym
M
He
dibromo
Bur
geminal
Alkane
Mechanism
20 alkeny/
carbocation
Y
Some allowe also reacts into
M
= - alkane
y
H
a some in^ this case
Brd
can meact trop or bottom
Exeples
limitations
·
fleat needed
·
No
rearragements
of
alkeny'
carbocations
· Alkeny)
halide
computes
v/
alkyne for AX
present
in solution
