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A comprehensive overview of organic chemistry reactions, covering key concepts, mechanisms, and examples. It delves into various reaction types, including alkene, alkyne, and ketone/aldehyde reactions, with detailed explanations of each step. Particularly useful for students studying organic chemistry, offering a structured and organized approach to understanding these fundamental reactions.
Typology: Study notes
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~
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
Hey
Bonds
Formed
Bonds
Broke
· C- Br
· C
· H-Br
3r
R
H
uBr
&egiozhem
Stereochem
Y
M
Alkene Alky1 Bromide
Mechanism
S Sa
Br
&
3r e
I
^
H -^
nucleophilic trepping
Examples Limitations
of (^) HL)" HE follow same^
decreases as atom size^ increases
MB r
HCl
HE
↑
Acid Catalyzed Addition of Alcohol
↓ y
Bonds foreed Bonds (^) Broke
0 · C
masO
in
a
no
· C
Ij
... (^) S R
Regrochem
: (^) Markovnikov Stereochen^
: Random
Altere
has CHOH CHOHr^
H
--
or
W
↑
↑
jo
R
↑
ja
x (^) -
1
R
I I
Exeples
limitations
·
must be (^) MePH
or a^10 alcohol
Acid Catalyzed Addition of
Carboxylic Acid
Bonds formed
Bonds Broken^6
·^ ((n) (-
Summary
t
· C
& 17
N (^) I'M
Reochem
: (^) Markownikov Stereochem^
: Random O
Alken z
↑ of Ester
ha CLOON
i ...
o
H &^ or
& (^) - O -
⑪
O H II &
I 1 H
⑪
↑
H
↑
jo
n
ja
I H H^ -
xp
R
I I
Examples (^) Limitations
⑭
Bromination in the Presence of Water
Broken BC
~ Halohydrin
· C- OH^
C(π)
Summary
H · C-Br
· Br-Br
R &
H
,
1
n
L
on
R
R
Regiochem
:
Markovik
a Stereochen
enant. -
Alcohol
Mechanism
B -Br
R
↑↓-
Bro an ↑ I^ -
H
=
-1) , L I^ H
, (^1519) H &^
I J^ It (^) R
I I > - O
/
(^7) -
H
enantiomer
j
-0H .
Br
H (^) I H Br or
can (^) attack
fr a H Br
↓
&
Exeples
Imitations
partial positive^ change
Bromination in the Presence of Alcohol
Broken BC
~ Halohydrin
· C- OH^
C(π)
Summary
H · C-Br
· Br-Br
R &
Brz
R (^) O
,
1
n
L
R ROH
Ver R
R Regiochem
:
Markovik
a Stereochen
enant. -
Ether
Mechanism
B -Br
R
↑↓
Bro an
H
=
n
d
J (^) It
/ 7
I (^) H
enantiomer
j
-0H .
Br
H (^) I H
Br &
can (^) attack
fr a #1 (^) ↓
Exeples
Imitations
partial positive^ change
Oxymercuration-Demercuration in
Presence of Acid
H
Bonds formed
My
Bonds Broke^ d
S
Summary 2 ↑
-Me
Et
I NS
- um (^) OR
D + -
/ (^) ROt
Regrochem
: (^) Markovnikov Stereochem : Random
Altern Ether
Same as^ last one
Exples
Imitati eul carboxylic
acid
,
Hydroboration- Oxidation
H
Bonds formed
My
Bonds Broke^ d
S
Summary
↑
Do
o
↑
H
↑
Regrochem
: (^) Anti-Markovnikov Stereochem : Syn (^) (M , OH)
Alkne Alcohol
Mechanism ro a
I-
R
For
&
i B
·
H
R
a
o
H
& (^) -
- : D
↑ (^) -
41
N
-- - (^) D
·
j
o
M of
oh
&
C
41
I ,,,,
O I^
=
%
L. H on
H
tenut ↑
BR=OH
....
Exeples
tenant
.
. Imitation
e on ester^ or^
an ether Can't
· Sturrs bulk^
C >
· when staggered
: ·
I substituents^ that were (^) APP on (^) the allee
· rotate
conforme so
App
· Added (^) RzB" I groups
should be^ gauche
Catalytic Hydrogenation
of Alkene
↓ y
Bonds foreed Bonds^ Broke
S
Summary
2 ↑
T
Regrochen
:
Stereochen : ~or solvent - Syn
Alkem Alkane
Mechanism
D Hz
:
: &
1 -
Y
Pd
m+al
Surface
Exeples
Limitations
C·
group compatibility
:
ester ,
alcohol , anime ,
2-
, aldehyde ,
GBr ,
2-
· 2 metal
: PtL Pd/(
·
Ozonolysis
↓ y
Bonds foreed Bonds^ Broke
h
S
↑
2
E
-min
: Stereochen :
Alkana 2
Mechanism -^ - [ o ·...]
O O &^
o ⑦
=^0 v L ⑧ -Mu
G (^) 0-
I S
Mr
T
↑
↓
p
L -o^ ozonice
~
T
=
It
-See
Exeples Limitations
Catalytic Hydrogenation of Alkyne (Lindar’s Catalyst) H Bonds formed yBonds Brok a
H mary · C-H
H - H (z)
Regrochen :
Stereochen :
Alkyne
Mechanism
need to know
Exeples Limitations ·
group compatibility
can be (^) in molecula · phenyl ,^ allow , ester ,
, amive^ , latir , aldehych, (not altered) C-Cl , C-Br ·
E alko · terminal
allee
·
Catalyst :
,
,
([ITE)
Catalytic Hydrogenation of
Internal Alkyne to (E) Alkene
H
Bonds formed
May BondsBrother
reduction
Summary
2
A
. Nita Regiochem
: Not Stereochen :
Syn
Alkyne
(t)
Mechanism
&
Na atros in^ liquid (^) ammora Eject 12-^ that floats around^
in solution^
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
compatibility
:
can be^ in molecule (maltired)^
,
,
anive
can't be in mobenze(changed)
:
phenyl (^) ,
, aldehych ,^ ester,
24
c -Br , C-E ,
,
, ferminal carbox
SN2 with Alkyl Halides
H
Bonds formed
Bonds
Broke
o
· (^) L-C
Summary
2 ↑
Na
OE-R
(
-X (^) - R
Alky/Halide
Alkynyl
Regrochen
: Stereochen :
Anion
↑ A
d
--
Nach C^
-- L
Nu backside approach
Exeples
limitations
Requirements
:
In
Br- (^) CHz
Br3i
Bru
Br - E
C(sp)
,
H-s ,
H-
, c group
in electrophile
(pka224)
formation
Electrophilic Addition to Alkynes
H
Bonds formed
My
Bonds Broke d
S
Summary
= zegHr^
↑
2
T
A , Ch
Rochen
: Markovikov
Stereochem : Random
Alkym Alkase^ alkym
He
dibromo
Bur
Alkane
Mechanism
20 alkeny/
carbocation
Some allowe also reacts into
= - alkane
Brd
can meact trop or bottom
Exeples
limitations
·
·
alkeny'
· Alkeny)
halide
alkyne for AX