Organic
Chemisty
Ahmad Mahareeq
1
Review
⑳
Bonds
⑳
:
Chemical
·
·
-
-
·
the
within
ionic
ionic
cation
covalent
overlapping
·
no
.
·
or
no
.
orbitals
8-bond
=
unpaired
H
I
-
C
H
-
H
=
properties
:
Boiling point
i in
in
4 + 4x
atom
electronegativity
=
2
Solubility
....
Dipole-Dipole
London force
(P-P)
it-bond
of
-
·
:
valence
H
atomic
difference
to
structure
CHy
:
Physical
-Melting point
nonpolar covalent
according
Lewis
:
molecules
between
-
theory
by side
=
·
anion
-
end
of bond
·
coordinate covalent
between
to
side
polar
,
Bond
:
send
·
molecule
covalent
,
:
·
Physical
,
H-bond
Theory
USEPR
:
molecular structure
polarity
>
-
M
>
M
Symmetrical-
domain
Electron
C
H
-
0
>
-
nonpolar
triple bond
,
H
↑
-
=
>
-
o
Fo
London
nonpolar
polar
Corces
:
double bond
H
M
>
=
tetrahedral
>
-
domain
I
=
,
109
.
5:
H
Hybridization
new
energy
Why ?
1
.
.
2
and
no
of atomic orbitals to
mixing
:
new
shape .
actual
electron domain
angle
>
-
I
>
sp
>
3
-
sp2
>
>
Sp
+
one
.
.
one
hybridization
Y
2
expected
expected
bond
of actual
.
give
&
tetrahedral[109 5 "
.
trigonal
Linear
planar
120
°
180
new
orbitals
with
HCN
1
4
+
+
5
=
-r
H
CO2
10
M-10
=
=
:
!
-
-
2x6
+
20
:
-
16
-
-
H-CEN
4
:
I
:C
:
=
16
4
=
2
1
+
O
=
EO
:
linear
+
c
Sp
>
-
>
-
Sp
:
ff If
H
C OC O
C
12
S
O
S/I
Pz
Bond order
C-N
2-H
:
:
sig
1
·
P2
Py
-
O
triple
3
single
I
O
O
:
0= C
=
.
0
>
most
stable
:
sp
CO
:
:
CEO
:
Py
CO2
:
I
o= C -
is
because
more
it
stable than CO
has
more
resonance
Resonance
than
more
-
lone
lewis structure
one
i2
pair
or
,
sp"
sp
or
·
stability
increase
atom
Delocalization of electrons
>
-
:
Stable Lewis structure
Formal
Stability
1
2
zero
.
no
negative charge
.
valence
E's
-
around atom
:
more
.
charge
positive
charge
high electronegativity
low
electronegativity
on
on
O
O
atom
.
atom
.
O
O
O
O
G
E
C
stable
more
-
-
(equal
C
O
G
in
stability (
O
&
Resonance
Bond order
q
hybride
=
=
It
Itz
movement
of
by using
electrons
rich
in
i
to
poor
::
↑
, CH
Ch
t
start from
arrows
:
Fede
:
,CH
C
,
CH
,
Acid
Base
proton donor
proton acceptor
conjugate
conjugate
electron
pk ,
base
acceptor
electron
acidity
equilibrium toward
donor
pk ,
the weakest
acid
acid
and base
basicity ↑
in
e.
Kinetici
of
Rate
&
[P
K
n
is
.
is
m
=
rate
chemical
1
elementary.
K [A] "
=
constant
order of
reactio
n.
CB
.
reaction
equal
to
coefficient
if reaction
2
3 : Alkanes
⑳
Hydrocarbons
Saturated
and Cycloalkanes
of
consist
Unsaturated
bond
double
:
bond
triple
Aromatic
·
benzene
contain
:
Alkane
structural formula
type
Expanded
Cormula
-
number
:
H
H
H
&
H- C
i
condensed formula
:
H
:
,
C
I
H
CHzCH
If
I
C
- - -
↑
CH
,
in
molecule .
connected with each other
are
I
CHg
atoms
molecule.
CzHf
-
of
Lewis structure
:
H
↑
C
and
:
how atoms
:
in
H
their derivatives.
or
their derivatives.
or
formula
molecular
·
:
benzene
:
Cutentz
CHy
alkyne
doesn't contain
:
.
alkene
>
-
>
cycloalkane
and their derivatives.
benzene
Aliphatic
hydrogen.
and
carbon
bond s alkane and
single
:
⑳
H
-
H
CHy
Lewis
:
USEPR
H
in
↑
H
-
the
away
C
-
H
plane
of
H
I
*
H
III
H
tetrahedral
H
viewer
1
C
.
109
As
H
X
out of
plane
toward
3D structural
formula
viewer
:
Ball and stick
saw
Cyttz
horse formula
H
:
HI,
.
C
⑭
H
Line
angle
H
C
/
↑
Cormula
:
bond-line
carbon
=
other atom
angle
than C and
I
appear
H
.
5
CHu
Cotte
Cate
CaHsO
Cuttio
C
·
O
of
Shapes
·
·
·
oragnic compounds
OH
:
open chain
ring
,
cycle
branched
Alkane
Alk = no of
.
carbons
an
en
yn
=
=
=
single bond
double bond
triple
bond
·
e
=
no
functional group
CHu
methane
:
CH , CH ,
ethane
:
CHsCHCHs
CHs(CH2l CHs
,
CH (CH2) , CHs
,
·
propane
:
butane
:
:
pentane
CHs (CH2uCH : hexane
CH ,
(CH2)5CHs
CHs (CH2) , CH
CHs
(CH2) CHz
CH, (CH2) & CH3
Cultio
:
relationship
heptane
:
Octane
:
nonane
:
decane
:
Chain
is
:
:
constitutional
branched
isomers
:
isomer
:
molecules
but
1
differ
.
differ
in
.
differ
same
in
isomer
order
of
formula
molecular
formula
.
structural
in
constituent of
constitutional
2
with the
connectivity
:
.
atoms
in
space
connectivity
:
Stereoisomer
which
of the
following
are
constitutional
isomers ?
O
OH
CH , O
Cuttio
CyHz
CH , O
CH
~
,2
Cult
same
molecular
Cormula
~
the
same
s
Cat
CsHiz
,2
molecular
same
butane
:
Cormula ?
,
-
20
o
36
>
isobutan
V
V
yes
o
2
jo
no
o
↑
CHsCCHe CH
,
(CH3)
,
CH
Cormula ?
isomers
d
yes
:
no
N
*
not
constitutional
constitutional
isomers
zo
isomers
·
CHs(CH2)
isopentane
y
,
CH ,
CH CH
,
,
CH(CHs)
·
,
(CHs)
hexane
constitutional
,
X
pentane
not
same structural
:
,
neopentance
C
isohexane
1
20
o
yo
CHy (CHeSyCHg
2
y
CCHelzCH(CHz)
,
CH CH CHCH , CH CHs
,
,
,
(CHCH2) CHCHs
,
zo
(CH3) CHCH(CHz)
CH
,
CHzCH C(CH )s
,
,
order of carbon
methyl
:
secondary
tertiary
*
quaternary
:
:
:
order of
*
*
primary
carbons.
carbon
connect with
carbon
connect with three carbons
. 3
carbon
connect with
one
carbon .
two
carbons
.
:
It
connect
with
primary
carbon
-
following
from condensed to line formula ?
CH , CH2C(CH3)2CH2CH(CH2CHs)2
CH3
CH2CH
·
,
CHz CH CCH CH
,
CH2CH
,
CHzCH(CH(CH3)2) (CH2)>CH
CCH
,
.
.
:
CH ,
2
4
carbons
.
four
:
CHs
. .
connect with
with
secondary carbon
secondary It connect
tertiary It connect with tertiary carbon
e
CH3
to carbon order.
:
Convert the
CHs
no
carbon
hydrogen
according
*
connect with
Carbon
:
primary
*
:
CH2CH2CHs
z
Nomenclature of alkane
IUPAC
·
Common
·
systemic
#
order alphabetically
substituent-A-parent-suffix (functional group
position of substituent
-
# before
.
parent
Alkyl group
CH3CH
-
,
,
-
CH CH ,CH
,
propyl
isopropyl
(CH3) , CH-
,
alkane
ethy)
-
,
CH , CH CH
(CH
=
:
methyl
CHz-
CH ,
position of functional group
>
-
of substituent
name
1
name
name
name :
#-
:
CH2-butyl
,
ICHCH-isobutyl
CHaCHCHs
d
(CH3)s C-
Sec-butyl
tert-butyl
It
(R)
3
.
2
Cycloalkyl
ex
:
cyclopropyl
alkene
.
3
:
:
methylene
vinyl
Phenyl
benzyl
halo
flouro
8
.
9
lo
:
:
OXO
.
=
-
z
X-
amino
.
CH2 CHCH2-
GHsCH
:
hydroxy
.
CH-
Colts-
:
6. nitro
7
=
:
:
bromo
=
,
CH2
:
benzene
.
5
CH
:
·
allyl
.
4
cyclobutyl
,
mercapto
BrF
-
:
NO ,
:
OH
:
NH2-
-
O
:
-
-
=
SH-
,
...
Naming
Rules :
prefix
1
Parent
.
parent
:
suffix
the
longest
attached
carbons atom
continuously
with each other2
.
numbering the
carbons of
parent. Starts from the
give the carbon that connect with substituent
nearest substituent
the smallest
number.
5
G
4
7
f
X
I
3
I
5
>
substituent
4
6
2
3
I
2
7
I
f
U
3
6
55
4
7
G
2
3
4-methyl
octane
E
I
X
(methyl)
2-methyl
2-methyl
.
3
if there
.1
3
are
2-methyl pentane
propane
3-methyl pentane
butane
more
than
one
identical substituents
.
>
-
the
add
·
prefix
di
:
tri
,
2 2
2
.
the
same
:
carbon
multiplication separated by
number with
same
in
substituent
tetra
,
before substituent
-dimethyl
comma
name
.
propane
31
.2
3
identical
.
>
-
number
·
add
substituent
:
di
,
different carbons.
separated by
of carbons
prefix
on
tri
,
tetra
comma
before substituent
I
3
42
2
,
3-dimethy
butane
name
.
different substituents
.3
3
.
start
>
-
from the
numbering
according
name
to
nearest
alphabetical
one
,
then
order
g
54
3
I
6
2
2
&
Y
5
3
I
6
:
3-ethyl-4-methyl
4
hexane
5-ethyl-2-methyl heptane
7
2
3
7
3-ethyl-2 6-dimethyl heptane
I
,
O
7
...
↓
54
2
,5
.
5-trimethyl heptane
I
I
3
7
5
3 3
6
Y
5
.
5-trimethyl heptane
6
&" &
,
,
3
.
4-diethyl-2-methyl
hexane
3-ethyl-4-isopropyl
hexane
writing
the
7
9
56
4-isopropyl-4-propyl
&
I
3
2
·
O
C
Cyclic Compounds
carbon atoms
·
·
·
nonane
saturated
connected
with
each other to
form
unsaturated aromatic
ring.
,
,
carbons
homocycle
heterocycle
-
Cycloalkane
:
:
carbons
homocycle
and other
saturated
atoms
0, N
,
P ...
ring
Enten
CH2
600
CHz
CH
CH2
CH2
,
cyclopropane
cyclobutane
Che
CH2
T
/smallest
ring)
cyclopentane
cyclohexane
substituent
parent
cycloalkyl
:
.
cycloalkane
:
numbering
start
from the nearest substituent.
methyl cyclopropane
I
2
3
1-ethyl-1-methyl cyclopropane
I
32
2
I
Y
3
5
3-cyclopropyl pentane
↑
2
3
I
2
1-ethyl-3-isopropyl cyclohexane
2-ethyl-1 4-dimethyl cyclohexane
,
U
isobutyl cyclopentane
1-tert-butyl-3 5-diethyl cyclohexane
.
4
conformation of alkane and
conformation
due
cycloalkane
arrangement of atom
is
:
of (C-C)
to rotation
bond
&
:
molecule
in
in
.
start from two carbons.
types
result to
rotation of
result from
H
H
H
of conformer
ki
C
↓
C
carbon
"
11434
↳
600
H
H
:
#
kill
H
H
carbon
H
rotate
C
I
H
H
eclipsed
front
carbon
bond
stable
staggered
projectionformula
back carbon
staggered.
H
C
more
Newman
and
eclipsed
:
=
=
:
Circle
dot
-
torsional
o
(eclipsed)
strain
HH
-
H
H
H
H
Eclipsed
.
space
↑
H
o
#
O-
/
H
staggered
more
Conformation of ethane
stable
:
CH, CHz
H
HH
I
I
60s
d
-
"
3
H
↑
O-
/
H
"O
/
#
60
HH
°
&
-
-
H
H
H
H
↑
2
H
H
H
H
H
#
3
60
60
-
H
H
H
2
HH
H
H
H
↑
O-
/
H
#
60
-
N
HH
HH
HH
"Eclipsed
·
it
·
H
Hp
H
m
PE
.
-
-
-
n
staggered
-
·
··
H
If
H
6
120
300
240
188
ethane
°
°
s
CHCCH2CI
Y
H
a
#
Y
H
Cl
&
Q
-
H
Cl
T
I
>
-
gauch staggered
anti
staggered
CIH
CICI
as
stability
I
:
I
-
H
H
H
H
HH
Cl
#
IV
eclipsed
The most
The
eclipsed
stable
highest
conformer
energy
:
#I
in
1
.
2-dichloroethane
is
:
I
IN
II
Which of the
Y
following
the
is
H CH
CHE
Q
,
most
stable
CHz
-
H
CH3
HH
CH ,CH ,
CHs H
CHs CHz
-
HA
CH /CH
,
,
Name
H
H
CHE
H
steric strain result
the
following
:
from
CH2CH3
"
CH
Q
/
,
CH3
3
.
4-dimethyl
hexane
bulkiness of
CH2CHz
group
conformer ?
2
.
following
of the
which
3-dimethyl
butane ?
H
CHE
the most stable conformer of
is
↑
CH ,
-O
CHs
&
H
CH
c
I
,
-
CH
H
CHE
in
-
cit
cha
CH ,
,
,
cycloalkanes
H
T
2-dimethyl
:
cyclopropane cyclobutane cyclopentane cyclohexane
,
60°
1
-
angle
,
,
109 5
.
strain
H
.
H
2
H
---
i
C
H
"4H
C
I
Eclipsed arrangement
torsional strain
Ring
H
&
/
2,
Conformation
c
strain
butane
90° 109 50
.
)
2)
angle
strain
Ring
forsional strain
strain
>
108" - 109 50
envelope
.
cyclohexane
:
The most stable
-
1)
2
Stable
cycloalkane
Chair
109 5
.
staggered arrangement
axial
up
equatorial
Flip
down
H
H
-
Boat
&
1
.
4-diaxial interaction
(Hagpole
interaction)
Steric strain
Monosubstituted
cyclohexane
5
:
methylcyclohexane
H
Hill 1111111111
.
H
-
C
-
H
H
H
CH3
more
Steric
*
interaction
between
C , and C
diaxial
interaction
,
The most stable conformer
is
when
the
substituent
CH ,
more
stable
on
the
Cels
stable
bulkiness
felts
more
than
Cis
>
decrease
stability
equatorial
bond
.
Disubstituted
geometrical
connectivity
cycloalkane
isomer
Two substituents
Cis
trans
they
up up
:
,
different
cis-1
·
,
of atoms
in
in ,
or
in in
,
out
physical properties
:
B
.
pt
.
M
.
pt
2-dimethylcyclopropane
trans-1
,
isomers
2-dimethylcyclopropane
=
·
.
space
out out
or
,
geometric
=>
and the
different carbons
.
,
or
Cormula
molecular
same
arrangement
down down
or
,
are
in
two
on
up down
:
the
:
differ
but
:
trans-1
,
3-dimethylcyclobutane
constitutional
cis-1 ,
ht
h
b
2-dimethyl cyclobutane
trans-1-ethyl-2-methylcyclopentane
e
isomers
same
"
1
Disubstituted
1
the
on
.
,
cyclohexane
same
if there
carbon
are
equatorial
-dimethylcyclopentance
where two substituents
groups
,
the
largest
. .1
2
different carbons
.
on
position
trans
(I)
according
to
one
equatorial.
should
be
on
I
more
on
one
C
Cl
.
is
.
I
2
on
:
different
bond
the most stable conformer
:
1 2
.
:
:
trans
Cis
(I)
(I)
stability
stable
:
I < IV
-
IT
Cis
(IV)
I
- if similar
>
if not
groups
similar
,
the
bigger
group
on
equatorial
22
.
.
position
1, 3
:
Cis
(I)
Cis
trans
trans
(I)
(II)
(IV)
most stable
.3
2
.
Position
1, 4
trans
(I)
:
trans
Cis
cis
(IV)
(H)
(I)
most stable
Which of the
following
is
the most stable
Lis-1-ethyl-3-methylcyclohexane ?
more
stable than
the last
one
/
trans
,
most stable
I-4
trans
X
Cis
?
Cis
Physical
alkanes
nonpolar
are
force (the
weight
Boiling point
low
is
in
the
than
and
,
insoluble
.
3
increase
Melting
increase
packness
H
no
chain
Solubility
2
.
are
:
>
-
form London
.
gases
as
no
of carbons
.
,
density
is
.
low
of
.
>
-
carbon
increase
branched
alkanes
and soluble
water
in
point
weight
molecular
as
in
nonpolar
increase
but
M
=
0
>
London
H
HI
, , ,
force
2
H
H
according
to B
pt
.
:
I
I
T
>
-
Y2
.
solvent
irregular
effect.
h
I
.
:
Hill
Order
B
:
1
he
lower
.
H/ 1 1 [
H
dispersion
:
same
open
molecules
weakest bond)
low molecular
I.
of alkanes
properties
62
62
#I
,
due
to
pt
Chemical
they
properties
are
.
2
+
202
:
>
-
CO
,
+
2 H 20
Free radical substitution
R-H
Cl
=
:
saturated
unreactive
1. combustion
CHy
of alkanes
R-C
+
+
energy
reaction
:
H
UV
Cl
↓
CI
.
..
C1-
radical
↓
Cancer
Quiz
>
Homolysis
4:
⑳
Alkenes
Alkene and Alkyne
unsaturated molecule that consist of
are
:
double bonds
if alkene consist
*
*
cycloalkene
with
The smallest
is
alkene
bond,
double
one
Cntan
or
more
general
CnHanz.
two carbons
s ethene
is
the
-
double bond
one
one
.
of
molecular formula
*
⑳
.
H
H
c
C
=
IπT
H
H
58
sp2
·
trigonal
planar
bond
C P-C , P
,
bonds
Yc
1
-
C
-
Hsp2- S
sp-sp
C
120
Alkynes
:
are
unsaturated
molecular formula of
*
General
*
The smallest
H
-
C
=
C
-
H
is
180
alkyne
with
one
triple bond
ethyne (acetylene)
2π
36
sp
linear
alkyne
,
triple bond
molecule with
bonds
bonds
-
-
1 sp-sp
2
sp-S
2
is
bonds
.
Cnten-
6
Naming:
1
2
Select the
.
start
.
from the
numbering
unsaturated bond
unsaturated
.
3
chain that contain
longest
when
bond
write the
suffix
>
-
=
:
=>
Y
>
take two
s
name
position
.
yne
-
pentene
or
I
5
3
(
5-methyl-1-hexene
I
.
5
pent-1-ene
2
U
4433
3
2
2-ethyl-3-methyl-1-pentene
.
of unsaturated bond
ene
1
3
nearest to
sequence number
I
5
6
is
.
.
the smallest bond
using
end that
unsaturated bond
by
methylene
=
vinyl
allyl
-
-
CH2
CH
=
CH2
CH2CH CH2
=
CH2
methylenecyclohexane
allylcyclopentane
3
2
3-methylcyclohexene
I
↑
Y
2
3
1-isopropyl-4-methylcyclohexen
4-methylene cyclohexene
CH2
180
3
2
I-propyne
I
I
Y
3-methyl-1-butyne
2
3
I
2
3
45
6-dimethyl-3-heptyne
6
7
Geometrical
cis/trans
CH2 CH2
=
ethene
isomers
in
alkene
:
EIZ
CH , CH
=
propene
CH2
CHsCH2CHICH
CH3CH CHCHz
=
,
I-butene
constitutional
2
-
butene
isomers
CHyCH
H
=
CHCH ,
CH,
H
C
=
C
C
CH,
CHE
B pf
.
I
Geometrical
=
C
H
isomers
CHE
B pt IC
4 co
.
trans-2-butene
cis-2-butene
London force
↓. molecular
2
.
surface
:
weight
area
more
surface
bigger
which of the
1. CHs CH
=
((CH3)2
. CH , CH2CH
2
.
3
.
4
.
5
following
=
CHCHs
(CH3)C C(CHz)
=
,
(CH3)CHCH CHCH2CH ,
=
Coltio
molecules exhibit
Cis
C
Cla
stable
cis/trans
area
isomer
?
=
H
H
,
Rules for
1
.
Double
cis
trans
:
bond
. Each carbon of
2
double bond
attach with two different
groups
=> on
the
=> on
the
same
side cis
opposite
side trans
Name the
following
:
(CH3)CHCH-CHCH2CH ,
2-methyl-3-hexene
trans-2-pentene
6
-"
7
9
2
Do
7
2
3
·
cycloalkenes
From
3-7
·
2 trans
I
Y
,
4 trans-2
.
4- heptadiene
2
3
exhibit
only
is
I
cis/trans
3
trans 7 cis-1 3 7-nonatriene
,
.
,
isomerism ?
isomer
cis/trans
1
,
2-dimethylcyclopropene
1
,
2-dimethylcyclohexene
transcyclooctene
ciscyclooctene
El2
1
.
system
groups
:
that attached
classified
into
higher priority
direction of (1)
2
.
.
(1) at the
C
2
=
C
C
1
H
-
2
-
-
,
H
,
2)
if there
.
3
-
C
to
atomic
number
CH
(H
,
=
CH2
C C)
.
atomic number
C
-
atom
C
are
-
the
-CHBr
CHCI
(H
E
2
higher
if the first
.
=
2
:
atoms with
.
=
(2)
E
PriorityI according
Rules
=
I
2
Z
side
bond
I
2
I
priority
lower
different sides
at
I
and
(1)
same
:
carbon that make double
each
with
CH
are
,
0
-
H , Br)
CH,
then
same
-
is
higher priority.
=
go
CH
to
analyze
CH , OH
(H
,
H Of
,
-
CECH
(c
,
C, C)
C
CH2C
,
-
C
the other atoms.
(H H Cl)
multiple bond, repetition
-
-
,
,
of atoms.
E-3-methyl-2-pentene
'CH
i
>
H
,
=
CH H H)
,
,
,
c
zH ,
HzCH ,
(C
.
H H)
,
!
CH H 21)
H
,
,
H
HO
E
HO
(H
,
HEN
Cl
# C)
,
I
2
HEN
,
CH
,
,
H <K
Cl
E
H
HO
H
HO
,
(H
,
0 0)
,
2
Type
number
(,
(C
.
C
.
H)
(C
,
H H)
,
O
(C
HO
O
HO
then
(0
.
0 01
,
Q
O
②
,
C
,
E
H)
O (H
,
H H)
,
7
Cl
~
-z
Physical properties
and
alkene
*
*
of alkene
alkyne
are
force
>
dispersion
insoluble
in
E
and
alkyne
nonpolar
molecule
boiling point
is
:
so
water
.
.
pt of
of terminal
that
is
alkyne
B.pt of
alkane
Because
Hydrogen
London
low
.
B
Acidity
form
they
molar
mass
is
alkene
bigger
:
attached with sp carbon
acidic
.
is
pka
HO-H
HCEC
H2C
=
.
-
CH
HzC- CH2
Acid
15 7
25
increase
H
44
acidity
H
5/
H
-
-
:
sp-more
>
-
more
acid
.
Sp > sp" > sp3
s
%
>
-
stable
more
anion
electronegativity
>
-
stronger
HCEC-H +: H
amide
s
pKa
.
acid
s
HC = Ci
,
alkynide
anion
base
.
W
.
C
.
z
NH
+
anion
base
w
.
c. acid
25
=
38
Forward
RCECH
+
sRCEC: Na
NaNH2
very strong
and
CHICH
+
NaOH
NH ,
+
base
Nucleophile
CHEC Na
:
+
H2O
.
15
7
25
w
.
acid
w
.
base
s 2
.
.
base
s c
.
.
acid
Backward
1-alkyne
Quiz
1-alkyne
alkene
or
+:
+
NH
Of
allane
X
+:
NHS
or
OH
X
5 : Reactions
⑳
free radical
substitution reaction
RH
(2
Cli
C
Cl
R
:
.
of Alkene and
R C
s
-
.
+
Cl
RH
>
R
+
Cl
-
RC
+
.
:
H
initiation
.
+
.
+
Alkyne
HE
propagation
termination:
Cl
.
R
.
R.
+
+
+
Organic
1
.
Cl
R
CI
-
.
-
.
reaction
.
2
Elimination
.
3
Addition
Reduction
:
RR
RCI
types
:
substitution
Oxidation
Cl2
>
.
:
:
replacement
removal
unsaturated bond
.
convert to saturated bond
⑳
&
,
=
I
C
s
-
unsaturated
break
C-CI
-
saturated
I
28
sp3
sp2
Trigonal
tetrahedral
planar
Addition reaction
Addition
:
=
&
&
C
=
C
-
/
=
C
-=
\
=
E
-
-
CHBr HI HCl)
,
+
+
HA
H20
.
=
THF
-2) NaOH H2O
.
c
-
GG
Hydrohalogenation
-
C-d-
o
Hydrogenation
-
I
CCls
2
1) BH,
↑
C-C
I
HX
+
,
C
↑
Niorp
He
+
I
,
reduction
e
Halogenation
Acid
Hydroboration
catalyzed Hydration
oxidation
↑
c-c
/
1
1) BH . THF
-
-
&
C-C-OR
2) RONa H2O2
-
I
.
Reaction properties
1
than other
isomer
1.
Addition of
HX
:
HBr
,
oxidation
that
prefer
one
constitutional
.
reaction that
:
halide
hydrogen
HCI
reaction
:
Stereoselective reaction
.
2
Hydroboration
:
reaction
regioselective
.
&
prefer
one
stereoisomer than other
.
Hydrohalogenation
:
HI
or
regioselective
-
=
c
+ HX
/
Ex
:
CHICH CH2
=
1-
-
CHsCHCHs
propene
connect
with
+
CHgCH2CHL
:
addition of H20 (acid
hydrogen
-
HC
+
Markovinkoves Rule
In
-C
Hy
s
catalyzed)
carbon that
or
has
HX to
greater
,
unsaturated bond
no
.
of
hydrogen
.
What
is
the
product of
following
the
HBr
+
:
Br
t
&
Br
2-bromopentane
not
3-bromopentane
regioselective
I
HI
+
Hol
-
regioselective
&
not
&
regioselective
CI
2
Mechanism
*
Chlorobutane
:
elementary steps that describe
bond
breaking and forming
in
*
movement of
*
of
the movement
arrow
starts
neutral
anions
:
:
represent by
from molecule rich
Cl
,
,
the reaction
H2O
I'
,
,
in
HaS
OH
,
,
electrons
RNH2
NH2
,
,
arrow
,
C C
,
=
,
,
describe
:
Lewis Base
ROH
occur
by representing
electrons.
electrons
NHz
reaction
the
how
are
RCEC'
,
...
...
(Nucleophile)
:
end to molecule
*
neutral
cation
BH
:
E
Nu
*
Steps
,
in
HC
Fe
Lewis acid
,
AlCIs
,
HsO",
,
E
Nu
two I's
*
Hydrogen
,
Carbocation
:
electrons
in
poor
,
SOs
.
. . .
...
Free radical
=
(Electrophile)
mechanism
one
reactants
:
mechanism
diagram
,
activated
complex
intermediate
,
,
product
explained by diagram called potential energy
represent the progress of chemical reaction
can
that
be
vs
.
potential energy.
CHICH CH2
=
Mechanism
>
CHzCH
=
+
HCI
CH, CHCHs
d
electrophilic
:
CH2
+
H
-
C
addition
rxn
CHzCH"CH
:
2)
C
+
:
/
CH
:
+
8:
-
.
CHe
H
E
Nu
EAST
m
CH3
-
+::
,
Hs
i
H
+
.
C
+
CHe
OW
R
CHse
,
AC
Cl
E
Nu
activated complex
.
H
intermediate
carbocation
H
A C,
.
-
CH,
III
C
Ho
CH,
P
Cl
Potential
A
C
.
A
C
,
.
.
Energy
:
ACC E
R
P
exothermic
D
R
endothern c
M
A C,
.
A
PE
.
.
"SH
I
P
(Progress
ratio
between
concentration
concentration
*
the
*
*
can
of
of reactant
product
disappear
x
+
Y
determined
be
the slowest
step
=
appear
time
per
to time
.
order of the reaction
from
the lowest
step
in
mechanism
.
the rate of the slowest
in
is
:
K[R] "[Rc]"
rate of reaction
peak
steps
of Reaction)
reaction
=
highest
two
-
chemical
rate Law
the
=
O
Rate of
or
peak
C
=
Reaction Coordinate
two
electrophilic
slowest
rate of
step
so
step
=
addition reaction
,
rate of
overall
reaction
.
carbocation formation
is
the
:
chemical reaction
=
K[alkene][HCI]
order of
rxn
=
2
8
Stability
of carbocation :
RS
H
!
↑
C
C
H'H
carbocation
R
is
group
>
-
>
called
is
donating
8
via
more
stable than
form
faster and
stable
more
:
t
t
yo
O
more
stable
t
t
*
2
R
Co
bond to
O
zo
more
stable
charge
.
more
S
-x R
...
positive
carbon
(delocalization)
localized
+
o
inductive effect
*
2
S
20
distribution of positive
~
S
+
2
,
H
1
electron
s
Which
+
H H
methyl
*
R
+
charge
Cl
Ex
+
:
HCI
&
+
Cl
Mechanism
major
-
n
:
H
-
HCI
H-shifts
7
V
t
+
zo
carbocation
:
rearrangement
Cl
:
-
*
*
Cl
Cl
carbocation
rearrangement
convert carbocation
1.
.
2
Hydride
shift
:
:
from 20 to
H-shift
methanide shift
:
°
3
by
:
.
CH- -shift
.
Note :
Check
:
if carbon
near
sp"
has
one
or
two substituents.
Br
+
HBr
&
+
Br
major
-
&
⑦
&
t
2
:
3
G
Br
HBr
+
&
Br
+
t
Br
major
CH2
HC
+
2
.
produce
*
obey
need
so
,
catalyst
use
convert
one
with
bond
Hydration
and
forming
H
.
.
is
poor
concentrated acid
to
it
:
and other with
OH
because water
H2O
water
by breaking
Markovinkoves rule
we
>
-
alcohol
bonds
2
Cl
addition of
catalyzed
Acid
*
I
HzO"
.
regioselective
.
electrophile
H2SOn
,
HPOy
or
mix
of them)
OH
+
H2SOn
H2O
2
:
propano
OH
+
H
HeSOn
O
s
+
,
major
Mechanism
electrophilic addition
:
1)
OH
reaction
.
-
H-
+
·
-
H
it
OH
-
*
2)
+
SLOW
+
H
:
H2O
,
OH
H -
↳
-
H
3)
+
*
Corward
*
backward
hydration
and
dehydration
AGA,
M
+
He
catalyst
produce
and
Hot
alcohol s
produce
alkene
increase
,
[Acid]
decrease [Acid]
,
heat
Halogenation
.
3
anti
is
*
Addition of Bre
:
addition
(add Xc
electrophilic addition
*
bridged
reaction with
bromonium
X
↳
C-
Ex
+
&
Xc
:
Laboratory
Mechanism
-
-
1)
:
C
=
C
-
-
Br
CCl ,
Bra
2 3
,
dibromobutane
double bond
.
identify
test used to
-
Br(colorless)
(orange)
electrophilic
intermediate
C-C-
↓
+
2-butene
*
-
ion
stereoselective
11
c
/
Cl
sides (
opposite
on
or
addition
.
:
Br-Br
-
-
CI
BO
Bri
d
I
-
-
-
, &
C-c-
bridge
④
BrT
2)
-
,
I
ion
Br
Bri
~_
-
-
C-C-
Br
+:
I
I
B
bromonium
intermediate
CH2Cks
Bry
+
Be
Br
Br
BrBr
Br
stereoselective
·
Cla
IIII/CI
7
CClu
CC
*
Cl
Methylcyclohexene
.
4
Hydroboration
*
produce
Without
*
*
-
oxidation
alcohol
rearrangement
AntiMarkovinkoves
It
no
.
reaction:
role
:
(It connect with
sp2
carbon
that
has
lowest
)
*
Syn addition
*
occur in
CH and
two
steps
OH
:
1.
are
added from the
Hydroboration
:
same
side)
electrophilic addition
,
add
H, Br
without carbocation.
.
2
Oxidation
:
(replacement
between OH and
boron)
1)
1-
BHz
.
OH
THF
1 - propand
7
2) OH H2O
propene
,
,
Bets
+
s
THE
Mechanism
H
1)
CHC
-
,
(tetrhydrofurane)
B
B
-
:
CH2
·
H
a
CHCHCH,
Hydroboration
CCHyCH2CHugB ECHsCH
2)
BH
:
-
=
2
oxidation
:
NaOH
(CH3CH2CH2'zB
Replace
OH
,
H2O
-OH
,
=
CH
>
=
CH
CH CH2 zBH
[CH ,
,
,
3 CH
H2O2
with
CH CH
B
CH ,CHOH
,
+
NaBOs
,
1) BHz . THF
H
&
"III
I CH,
=
2) NaOH H2O2
.
=>
OH
=>
OH
trans-2-methylcyclohexane
OH
OH
H2O
+
&
H , SO4
OH
OH
1) BHz . THF
&
2) NaOH H2O2
.
1) BHz . THF
&
CHO: H2O2
2)
OCHz
-
ether
RONa
sochium
-
C C
-
=
/
~
1)
2)
alkoxide
BHz THF
.
.
RO H2O2
&
-
-
-
OR