ADHYAY Batch Hydrocarbons LECTURE-5

properties of alkeneso-

alcohols)
Acid
catalyzed hydration of (formation of
:

* alkenes -

/H20
-on
n
(c 27
=

Bot

C3-CH= CH2
-
Addition n&
of
the
* it takes
place according
Rule double bond
Markownikoff's across the .

Accordingtothis rulethenegativepaltof leagent e ee

of hydrogen
-
atoms

130t
-
-
di

9-fo
130t
[ ,

Mo
- - n
*-13
115-M= CHI
7 7
us

%: formation
callocation
↓
H2
W
ReallangemenSee
-4- 3
 - * 120
7 - XI

⑰
7
- 1 2 ⑰
-
7 (20
,

7
--
shift ⑭
-
the

↳ a
s
-

⑩ - -
130
⑪ ->

②
-
I

⑧
[5
⑭
I
⑤ - --
136

Oxymeculation Demeculation : COMDM) :

-
-

120
yc =

c) HgCOAcz/THf ,

-
(ii) NaBH4/oF

-OAc-aclys group--o-1-u
THF
tetrahydrofman I )
-

xi = On
-
Hg(OAcz/ THE , H20
--
↳ NaBH4/
Note : -

->
-
In the addition ** on) takes
H20 (n place
ofwith out
omDin
Rule
malkownikoff's any searrangement
with
.

because in the mechanism callocation is not

formed
thereforepossibility of beanangement
no
-

z Hg[OAc)2
xi
-
/THF HO
A
,

b
,
7

(i) NaH4/ H
 (i) :
meculation
addition on &
- of My
: -

:
I
CHICH=CH2 >CH3 CH-C2
-

g
rgOA mesculinin
e

cyclic

- CHINg - -

Dememahoni
② :

wa
848 e
-11

At
[T [] on

cisHg(OAcI2/Thr ,
H20
>

(ii) NaBHnOn

In in
* omDin the OH comes
from the 10 first step
and it comes
from Naiy in the second
stels
-
 - xi
t
, (A
xig(OAcz/FHF si
MyCOAC2/THF D20,

H20 NABH4/on
7-
-
ji
(ii NaBHn/w
db

>
⑭ / i,
HgCOAc)2/THE
120

I
E
,

⑪ I
>

(i) NaBD4/OD

HgCOAe)2/THF
xi ,
D20
② --
7
i NaHul

④
Alkoxy
mercuration demeculation :-Lethers are
formed)

y c xi(ii)HgCOAC2/THE
ROH
>
,
=
7

NaH/ on
ether .

Mechanism is as ompin Do write it at

same
your
.

own :
43

-
- HgCOAcz/THF , CHON
7 -
) NaHn/oi
 oxidation
*
Hydroboration : (HBO) :
-
-

DiaH6/ THE
y =

> ) Hebro on
hat .

-
-
BeMITHE -
o

Liil H202/ O

*
Note ④ addition on) takes
-
-
The
of H20 (4 place with
Rule
antimarkornikoff's .

↳ luk
the
According thisto

that
,
the
negative part
bonded ealbon
of which
double
rages goes
to

of hydrogens
more no -

< Don
E
xisBzM6/ THE

(i) H202/ H
·-or

callocation
* Since them is no
formed in the mechanism
the
I Rule .
exn so we can
directly we
antimalkownikolt's
 is
i Hydroboration : Addition
of hydrogen
and Bon
-

THE
BgM6
>
2B13

I
[R I
-
:
7 -
R
d ·

-
↳membered transition
state

(the addition Bron & H takes

of side)
place fam same

Leyn addition)
↓
R Bi ReB
Hz
Nee
-
-

= =
~
R R

↓
(R-CHz-cHat, barane .
dation:
Ho-o ↓ R R-CHICHE
=

⑦
On -

0
-

H
I

Lj H
R -B
R
I
-

/
-

->
0 -
H
R
R
-

-0
-

↳
ele
,

trialkyl ↓
brane

R
Ro -
R -

R
R -o -R+
&
o

26go -n -an
↓ OR (RolzB
-B
E
=
! -> R!

Le bo
LORl
n
-
->

↓ Hydrolysis
0-0-H 3RION
H3B03
-

fol
*
,
-
15 Di
BCH6ITRE

·
xi) a

got te HrOr/On -

-
7

[HBOS
LOMDM)

E -di -
⑭ Hydroboration reduction (alkanes
formed)
:

are
-

i BgH6/THE
7 x -

i
-

(i) CHOH
alkane .

: Hydroboration
:
4) -

same as HBO

B gHoIHF <
R-CH2= CH2 (R-C2-CzlyB .

trially
burane
RI R-CHICH2-
(ii) action :

Ra ⑭- - -
RI
- d
R
-

R' h
↓
↳ As
3
R'H+As -
=<-
R-
R - + R'n

↓--4
⑰
Hydroxylation of alkenes-(vicinal diols
(1 , 2) diols .
as
famed)
① Rxx
of
alkene with cold alk Kinnon
(Bayer's reagent)
.

② Rxn
of
alkene with i
Oon/Pysidine]
(ii NASOz /420
I
/Leminx
reagent)
③ Rxx
of
alkene with
peacid followed by hydrolysis
④ Rxn
of
alkenes with
ICICLONg in <C followed by
(Prevost condition) hydrolysis
⑤ Rxn alkenes with
of 2/CH3COAG , woodward condition)
in H20 -