Excite Pure

FAST, FLUID AND READY FOR

ACTION
With an intuitive 10.1 touchscreen, essential connectivity, and plenty of power to keep your media moving,
the affordable Excite Pure is always fast, fluid and ready
for action. From its eye-catching style and brilliant battery life to the snappy performance you get from Android 4.2, Jelly Bean, you can keep this smart tablet by
your side all day, every day. Whether youre browsing
web pages, playing console-quality games, or watching
HD video, the powerful NVIDIA Tegra 3 mobile processor delivers a smooth, speedy experience. Theres
optional 3G/4G* for wireless access anywhere too. With
a micro-SD card slot, youre free to share your content
or expand your storage beyond the 32GB internal SSD.
So you can take even more entertainment with you on
your travels. Or enjoy it at home on your big-screen or
3D capable TV, using the micro-HDMI port. And if you
choose the attachable Toshiba Keyboard Cover*, you
get full keyboard functionality and system protection
in one - it connects to the tablet via Bluetooth 4.0, so
youre ready for pure productivity too.

* availability and configuration may vary by model and country

10.1
TOUCHSCREEN

AUTOBRITE
DISPLAY

MICRO PORTS

DTS PREMIUM
VOICE PRO

2 WEBCAMS
(FRONT &BACK)

BLUETOOTH
4.0*

Excite Pure
TECHNICAL SPECIFICATIONS
Excite AT10-A-104
PDA0FE-00901DGE
Processor / technology

NVIDIA Tegra 3 mobile processor

Super 4-PLUS-1 quad-core with 5th battery-saver core
High-performance 12-core NVIDIA GPU (1.3 GHz, 1 MB 2nd level cache)

Operating System / Platform

Android 4.2, Jelly Bean

Display

25.7cm (10.1) Toshiba AutoBrite WXGA high brightness touch display with Wide View Angle, 16:10 aspect ratio and LED side lighting,
internal resolution: 1,280 x 800

Solid State Drive

16GB eMMC

System memory

1 GB (onboard) , maximum expandability: , technology: DDR3L RAM (1333 MHz)

Pointing device

Virtual Mouse (supports external mouse via USB or Bluetooth),Capacitive touch display 10 points multi-finger support

Wireless communication

Wireless LAN 802.11a/b/g/n (Broadcom), Bluetooth 4.0 + LE (Broadcom)

Sound system

built-in stereo speakers, enhanced by DTS Sound , volume dial: via Volume Up/Down buttons,

Interfaces

1 x external microphone shared with headphone socket , 1 x micro-USB 2.0 , 1 x micro-HDMI-out , 1 x micro-SD card slot with
SDHC / SDXC UHS-I support , 1 x integrated 3.0 MP high bright camera with auto focus (rear), 1.2 MP camera with Ambient Light
Sensor (front) and built-in stereo microphone with Echo and Noise Cancellation

Battery

technology: Lithium-ion polymer, 2 cell, estimated sample figures:

10h Video Playback 100%
50h Audio Playback 100%
11h User scenario: 60% Web / 10% Video Playback / 25% Standby
7 days Idle mode (System Sleep, WiFi on, Mail check on, LCD off)
9 days Stand by mode (System Sleep, WiFi off, LCD off)
6 weeks System Off
3 days RTC Battery Life (from 5% of main battery)

Bundled software

DTS Premium Voice Pro (multimedia and voice enhancement), Evernote, Facebook, Google Play, PrintHand, Skitch, ThinkFree
Office Mobile 6.0 for Android , Toshiba Audio Enhancement, Toshiba Online Manual, Toshiba Photo Enhancement, Toshiba Video Enhancement, TruCapture: digitalisation of your whiteboard notes, Twitter

Bundled hardware

AC adapter

Special features

3D Acceleration sensor, GPS, Gyroscopic Sensor, e-Compass

Physical dimensions

261 x 179 x 10.5 mm, weight: starting at 0.630 kg

Warranty

2 years standard European (Limited) .

Enhance the standard warranty with one of our additional services to extend or protect your investment.
More info can be found on our website within the Service & Support area

COMPATIBLE TOSHIBA ACCESSORIES

TOSHIBA SERVICES
WARRANTY EXTENSION
Extend your standard warranty for up to 3 years before it expires for
additional reassurance.

Toshiba 10.1 Sleeve, PX1846E1NCA

Toshiba 10.1 Stand Case,

PX1847E-1NCA

TEG_EN_Excite_Pro_DataS_2013. All trademarks are acknowledged. Product specifications, configurations, colours, prices and system
component/options availability are all subject to
change
without notice and may vary from those shown.
Errors and omissions excepted. Android and
Google Play are trademarks of Google Inc..
2011 NVIDIA Corporation.
NVIDIA and Tegra are trademarks and/or registered trademarks of NVIDIA Corporation in the
United States and other countries. All rights reserved.

CPU performance may vary from specifications under certain conditions such as the use of battery instead of AC power, certain external peripherals, certain multimedia applications or network connections,
complex modeling software and in areas with low air pressure at high altitude (1,000 metres above sea level) and/or certain temperatures. CPU performance may also vary from specifications due to design configuration. Under some conditions, your computer may automatically shut down as a normal protective measure. To avoid risk of lost data, please make periodic back-up copies. For optimum performance, use your
computer only under recommended conditions. Please read detailed restrictions in the product resource guide, visit the Toshiba web site: www.computers.toshiba-europe.com and/or contact Toshiba Technical
Support. - Graphics processor unit (GPU) performance may vary depending on product model, design configuration, applications, power management settings and features utilized. - Part of the main system
memory may be used by the graphics system and therefore reduce the amount of main system memory available. - For PCs configured with 4 GB of system memory, the full system memory space for computing
activities will be considerably less and will vary by model and system configuration. - For information about upgrading your system memory please refer to the user manual or contact your local Toshiba service
provider. - One GB means one billion bytes, accessible capacity may be less. - Wired and wireless communication capabilities to be applied in countries where approved. - Battery life may vary depending on applications, power management settings and features utilized. Recharge time varies depending on usage. Battery may not charge while computer is consuming full power. After a period of time, the battery will lose
its ability to perform at maximum capacity and will need to be replaced. This is normal for all batteries. To purchase a new battery pack, see your accessories information that shipped with your computer or visit
the Toshiba web site at www.computers.toshiba-europe.com. - Small bright dots may appear on your TFT display when you turn on your PC. Your display contains an extremely large number of thin-film transistors
(TFT) and is manufactured using high-precision technology. Any small bright dots that may appear on your display are an intrinsic characteristic of the TFT manufacturing technology. - Weight may vary depending
on product configuration, vendor components, manufacturing variability and options selected. - Please check your system specifications to ensure optimal results. - Certain notebook chassis are designed to accommodate all possible configurations for an entire product series. Your selected model may not have all the features and specifications corresponding to all of the icons or switches shown on the notebook
chassis. - Performance may vary depending on product model, configuration, video content/format/settings as well as the performance variations of individual hardware components. Results were achieved on
select models and configurations tested by Toshiba at the time of publication.

toshiba.eu/laptops/tablets

Toshiba Keyboard Cover, black

(English), PA5132E-1EKB


...organic chemistry has literally placed a new Nature beside the old.
And not only for the delectation and information of its devotees; the
whole face and manner of society has been altered by its products. We
are clothed, ornamented and protected by forms of mater foreign to
Nature; we travel and are propelled in, on, and by them. Their conquest
of powerful insect enemies, their capacity to modify the soil and control
its microscopic flora, their ability to purify and protect our water have
increased the habitable surface of the earth and multiplied our supply;
and the dramatic advances in synthetic medicinal chemistry comfort
and maintain us, and create unparallel social opportunities (and
problems).
R. B. WOODWARD
(, )
( )



,
.
.

,
C.
C ,
+ C-1 .

H3C

H
C
H

H C 1
OH
C +
H
H

2
3


. , ,
.
, C-1 +,
C-2 + ( ), C-3
+ ( ).

H
2
+
H3C

C
OH
C
C +
+ 3
H 1
H
H

3
+

1
+

OH

, C
(2,5) (2,1), C
.

,
.

H3C
3

C
H

H
2

H
C1
H

 ,
C,
, (..
Cl). C
, .

H
+

2 + H

C +

H 1

Cl

Cl

1
+

, C
, + (..
Li). C
, . .

+
H
2
H3C

C
Li
C
C - 3
H 1
H
H

3
-

1
-

Li


, :

1. :
, - ( C
) . ,
,
.

, C (+)

.

H3C

H
C

O
+

C +
H

2. :
,
2-o .

CH3CH2COOH

CH3CHCOOH
Cl

( Lewis).
,
Cl ( )
.


(+).

O
CH3CHCOOH
Cl

H3C

CH
Cl




. :
,
,

,

.
.


,
( ).
,
.

.
,
CC
(
).


,
.

( ) .
,
( ), :

H3C C

O
O

H3C C

O
O

( )
(.. ).

CH2

CH2

CH3

H3C

H
H3C

H
CH3

H3C N C O H3C O C N

H3C N C O H3C N C O

, .

H3C N C O

H3C N C O

H3C O C N

H3C N C O




CC CH.
.

C2+2
(
) ( ).

 C C
. , C
, C
C .

, ,
C .
.

H3C

H
C
H

H
C
H

H
C
H

CH3

H3C

H
C
CH3

H
C
H

CH3
CH3

H3C

C
CH3

CH3

 IUPAC


C
.
-

,
n. n-,
(normal) ,
.

H3C

H
C
H

H
C
H

H
C
H

CH3

1. .

,
() 10 C

.

(I)

2. C ,
.
,
. ,

. () :
10
1
2
9

3
8
6
3
8
5
6
2
7
5
9
4
1
7
10
4

(I)

3.
.
,
-, - (
6
8
).
7
5
9
10
.
(I)
,
() 5--3,8

3
4

3
4.
1
,
2
1 2


3
6
8

7
5
.
10 9
4
() 3,8-5-(2-)
(II)
:
C
( ).

 ()

IUPAC.
,
:
H
H3C

H
H3C H2C

CH3
, iso-Pr (i-Pr iPr)

CH3
-, sec-Bu(s-Bu sBu)

CH3
H3C

C
CH3

-, tert-Bu (t-Bu tBu)

CH3
H3C

CH2

CH3



.
.
,
( ).

CC (
3 Kcal/mol),
() .

Newman.
Newman C
, . ,
CC
,
. ,
,
.


( ),
Newman.
,
.

.

Y
C

X
Newman

,
( Newman)
.
,
,
.


()
,
Newman.
H
H

H H

HH

H
H

(I)

H
H
H

H
H

(II)

HH

H
H

(III)

H
H

H
H

(IV)

H
H

(V)

() CH (
)
120,
( ) .
,
,
(
).

H
H

H H

HH

H
H

(I)

H
H

H
H

(II)

HH

H
H

(III)

(
)
().
60, CH ,
()
. ,
( CH) .

,
CH .

HH

H
HH

H
H

(III)

H
H

H
H

(IV)

H
H

(V)

,
(IV), 120
(V) .

(
)
.

C2C3 .

CH3
H

H CH3
H

H
CH3

H
H3C

H
H

, , .

( 180),
.
60 C2C3
,
CH3H
.

CH3
H

H CH3

H3C

H
CH3

H3C
H
H3C

H
H

H
H

gauche

60 ( 120)
,
60. gauche
,

.

H3C CH3

CH3

CH3

CH3

H
H
H

H CH3

H
H

gauche

H
H

CH3
H

H
CH3

60
,

,
.
, 60
gauche ,
360 .


C2 C3
Newman :
CH2CH3
H

H
H

H
H

CH2CH3
H

H
H

H
CH3

H
CH3

C2-C3 C2-C3

H
H

H
H

CH2CH3
CH3

CH CH
CH3 2 3

C2-C3 gauche
C2-C3

60
.
,
(
)
( 180),
.

 IUPAC

.
C , C

,
C ,

3

7
6

1--4-
4-

, C
.
3
1
2

1-

 ,

.

4

6
1

2
1
6

Cl

Cl

1--2- 1--6-o
2--4--1 1--3--7- 1--6--2-,
7 (2+4+1=7) 11 (1+3+7=11) 9 (1+6+2).

3
4

7
6

Br

2
3

6
5

Br

7
6

3
4

Br




CCC
109
.
.
,
.


.

,
,

109.

(
),
.

. ,
CCC 60.
CC
,
CC
.
,
,
.

H
H


.

, .

( -).

H
H

H
H

CH2

CH2
H

H
H


( CH) ,

.


.

'

'

'

'

'

'

'

'

' ( '
)

'

'

' '

'

'

'

.:


( )
'




(
) C-C
.

H
5
H
H

H
H6 H
3

4H H 2
H
H

4
H

.
(3 3
)
(3 3 ).

H
H

H
H H 6
5
2

3 H H 1
H
H

,
:

'

'

'

'

'

'

'

'

' ( '
)

'

'

'

,
.

H
5 H6
4

CH3
1
H
2

4
H
3

5
2

1
H

CH3



H
5 H6
4

CH3
1
H
2

4
H
3

5
2

1,3- :
1,8 Kcal/mol

CH3

o
(
),
1,3-
C-3 C-5. H

,
,
.

 1,3-

.
,
,
( )

. ,
.


H
5 H6
4

R
H
2

H
3

1
H

R
(Kcal/mol)
-F
0,25
-CH3
1,80
-CH(CH3)2
2,20


(/)
,
.
(
) .


1,1- .
,
.
, 1--1 ( )
. ( ) 1,55 Kcal/mol (1,80 0,25=1,55,
).




H
5 H6
4

CH3
1
F
2

4
H
3

5
2

1
F

CH3


. .
,
.
cis trans
(cis )
(trans ) .

 , 1,2-,
() () cis ,

( ).
, () (V)
, trans
.
H

CH3
CH3
H
(I)

H
CH3
(II)

CH3
CH3

CH3

H
CH3

H
H

H
(III)

CH3
(IV)



( ),
, ,
.

.
. ,
(CH3),
. sp2
( ) HCH 120.

H
H

p- e

sp2,
C-H

 :
1. , .
( ) .

Cl

CH3

H Cl +

CH3

2. ( ),
.

Cl

Cl

Cl

Cl


,
,
+
. C
(
), ( +
) ,
. , (CH3CH2)
(CH3),
.
,
,
C
.
H
CH3
CH3


,


.

H3C

C
CH3

H3C

H3C

C
H


(CH3CH3)
:
1. ,

Cl

Cl

hv

Cl

Cl

2. ,

(CH3CH2).
,
.
,

() (Cl*).

Cl

H3C CH2

H3C CH3
+ Cl

Cl

H3C CH2 +
H3C CH2Cl +

H Cl
Cl

3. ,
:
( ), ( )
( ).
,
.

( ).

Cl

H3C CH2
Cl

H3C CH3
+ Cl

Cl

Cl

H3C CH2 + H3C CH2

H3C CH2 +

H Cl

H3C CH2Cl +
Cl

Cl

CH3CH2CH2CH3

Cl



Gibbs .

( ).
,
:

F2>Cl2>Br2>I2
.


,
,

H3C CH2

CH2

CH3

Cl2
hv

H3C CH2 CH2 CH2Cl

1-
H3C CH2

CH

CH3

Cl
2-
60% 1 40% 2-,

.
27,3%,
72,7%.


,

, .
1-,
, 2-
,
2-.

H3C CH2

CH2

CH2

1-

H3C CH2

CH

CH3

2-

( )
, 1:4:5.


.
.

:
1.


2.


3.

R1

R3
R4

R2




.

,

( ).
&
.

(
).

R1
R1

R3
R4

R2

R2

R3
R4

R3
R4

R1

R1

R2

R2

R4
R3

R4

C-R1
180

R1

R3

R2

,

. (),

, - .
, ,
.


/
R S.
, R S.

:
1.
.
:
. H

. ,
(
) ,
( C , z=6 1
).
Br, , ,
Br (z=35), N (z=7), ( C z=6)
.

.
(. ),
. ,
-CH2CH2Cl -CH2CH2OH,
,
(Cl,
z=17) (O, z=8).

. ,
, . ,
,

. ,
(),
.

2. .

( ).
3.
. (
), R.
(
), S.



(>>>).
(
, )
,

.
,
S.

Br

CH2CH3

C H

Cl

 ()
,

.

:
1. :
, ()
.
()
.

(1)

= R

2.
. ,
.

(2)

3.
(

C).
.
C-

(3)

,
:

S
(1)

(3)

= R

(2)

 ,


:

Br

Cl

OH

Cl

Br

C
R

OH

( C-Br)
() .
,
R.

CH

OH

HO

CH2CH3
CH3

HC

CH3

CH2CH3

,
, . (
), (
).
S.
, .

OH

HO

OH

,
( , )
.
.
S,
R.


C, ( ) ,
C.


C.

C

C.

C2H5O

C Br

H
2

CH3

Br C H O
2 5
Cl
I
H2N

COOC2H5

A , -1
O
C2H5O C

1
Br

R1=

C OC2H5
1

1
R

C OC2H5
O O

S
N
C N

N

CH3

( ) C
CC. ,
R1,
(Br).
C,
R1 ()

() .
S.

 , -2

Br

R2

R2

CH3

Br
CH3

C2H5O C
H

N
= R2

Br
.
.
S
R.

 , -1
Br

I
H2N

H2N

Br

C2H5O

COOC2H5

3
R

Cl

R3

H2N

Br

, Br .

()
(R3)
.

B , -2
I

Br

C2H5O

H2N

R4

Cl

COOC2H5

C2H5O

Cl

COOC2H5

C2H5OOC
R4

OC2H5

Cl

.
R4
()
.


( )

( ),

. ,

[]D Beer. :
. []D ,
.
[]D, .
. R S
[]D.

.
,
[]D
.
.

 S
[]D= +3,82, R []D=
-3,82.
50:50 ( ),
.

H
HO

H
COOH
CH3

(S)-

HO

CH3
COOH

(R)-

. ,
S R (20:80 )
[]D= -2,29,
(+3,82)x0,2 + (-3,82)x 0,8 = -2,292



C, ,
.

C,
() R S
.
,
(22) , 2 .


, 3--2 ,
.

:

Br
(3S)

(2R)

H
CH3
H
COOH

Br

(3R)
(2S)

Br
CH3 (3S)
H

(3R)
CH3

COOH

Br

(2R)
COOH

H H
CH3

(2S)

COOH

,
(2R,3S) (2S,3R) (2R,3R) (2S,3S)
,
.


,
:
. ,
. .
Br
(3S)

(2R)

H
CH3
H
COOH

Br

(3R)
(2S)

Br
CH3 (3S)
H

(3R)
CH3

COOH

Br

(2R)
COOH

H H
CH3

(2S)

COOH

.
, :
, , , .
,

.

 (

), ,
.

2,3--2,3-,
:
I

O2N

CH3

NO2

H3C

H3C
I

NO2

CH3

O2N

O2N

CH3

H3C
I

NO2

H3C
I

NO2

O2N

CH3


,
: (
) CC ,
,
.

CH3

H3C
I

O2N

O2N

NO2

O2N
H3C

H3C

CH3
I

H3C
O2N B

A NO2

NO2

CH3
I
NO2
I

CH3

,
.
(2R,3S)-2,3--2,3 .

 () (
),
, .
(2R,3R)-2,3--2,3- ( ) (2S,3S)-2,3-2,3- ( ) .
H3C

CH3

O2N

NO2

I
CH3

H3C
I

O2N

NO2

NO2
I

H3C
I

CH3

O2N

NO2

O2N
I
H3C

CH3
I

,

.


()
, ,

.

, :

H3C

Cl

H
Cl CH3

(

C-C )

Cl

H3C
H
Cl

CH3

C-C
C

H3C

CH3

Cl

Cl



,
:

H3C CH2

CH2

CH3

Cl2
hv

H3C CH2 CH2 CH2Cl

1-
H3C CH2

CH

CH3

Cl
2-
, 2-
C, 1-
.
,
( C sp2 ). Cl2
R S . .


C

.


2S-.
F
Cl
Cl
F
R

2
F

Cl

Cl

1
F

F
S

Cl

Cl

, 1
C, R , :

F H

F
Cl

Cl

H F

Cl

2 3,

Cl

Cl

Cl

 4 5,
Cl
. ,
R S .
F
F

+
F

H
H

Cl

Cl

R
F

CH3

CH3

Cl

S
, 6 S :

Cl

Cl

Cl

F
S

Cl

8
7
6

1
2

34

3,5,5-

2
1

1,2-

2
3 1
4

2
3
1
4
5

IUPAC

(1R, 2R)-1,2-

 Newman
C-2 C-3 .
H

CH2CH3
H

H
H

H
H3C

C2-C3

CH2CH3

CH2CH3

H
H3C

C2-C3

CH3
C2-C3 gauche

H
H

H
H
H3C

CH2CH3

C2-C3

;
,
.

( )
.

HC

R S

.

H
C CHCH3

C
C
CH3

CH2CH3

C
C. C
( C).
C .
C,

( CC)
() .
HC

H
C CHCH3

CH3

CH2CH3

HC

C
CH3
C

CH3CH2
C CHCH3
H

Cl

R S

.

Cl

CH
3
O H

Cl

H CH3

 :
trans-1,2-
.
( gauche Cl 1,2
Kcal/mol
, gauche , ,
(1,2 Kcal/mol) 1,3 (2 x 0,52 = 1,04 cal/mol)

Cl

Cl

Cl
Cl

H
Cl

Cl

 (R)-2-o
.

.
) 2-o-1- R

Br

4
3

T S ,

Br H

Br
4

Cl
1

Cl
5

) 2-o-1-

,
:
Cl
Br

Cl

Br

Cl

Cl

Cl

Cl

Br

Br

Cl

Br

Cl

Br

1. Newman:

CH3
H 3C

H
Br

R S .
;

Br
CH3

Br

Br
Br

H3C

H
H

 Newman
H

CH3
H3C
Y

CH3

CH3
X

CH3

H
H3C

CH3

CH3

Newman

H
H

CH3
CH
3 3
CH

Newman

CH3

H3C

CH3

Br

H3C

H3C
H

KAI

CH3

H
H

H3C

CH3

H3C

CH3
H

Br

3
S-2-

CH3

Br

4
2

Br

Br

3

Br
S-2-

H
CH3

H3C

H
H

H
Br

Br

CH3

Br
H3C

CH3

2
4

Br

H3C

H3C
H

H
CH3
H

Br

H
13

Br
2

R-2-

Br

Br

Br 2

R-2-

Br

Br

Br

4
2

3
S-2-




C=C.
.
sp2 ,

120.
p
.
() (
).
,

.

 IUPAC
,
-.
:
1.
. ..
,

.

7
10
1
8

2
7

3
6

9
4
8 7
6
4
3 6 2 1
5
1
5
3
4
2

2. C ,
.
,
.
,
:

5
7

10

3
7

3. .
,
-, - (
).

.

:

5
7

3--7--1,6-

,
5--3,4-.
,
C
,
.

4
5

1
6

1
6

1
4

5
4


,
.

,
(),
-
.
. ,
,

(cis-)

(trans- ).

H
C C

R1
H

R2
R2

C C
R1

cis - trans ,
-.

.

 -
- .

cis
trans
, .

R3

R4

R3

C C
R1

R2

C C
R2

R1

R4

R1>R3 R2>R4

- ,
,

.

,
. ,
.
,
.


,
:
1 trans-4-2-,

.
2 ()-2--2.

( & )

.
3 ()-2--3-2-.
( &
-)
.

3
2
4
H

1
1

3 4

Br

OCH3

1
2

Br
3



:

,
.
,
+ .
,
, .

R2

R2

R3

R1

R1

R1




.
, trans-
cis-,

.

H
H

H
H

H
H

H
H
H H

H
H
H

H H

H H
H

H
H



,
( )
, .
:

. 2
(Pt, Pd, Ni )
,
:

CH2

H2

CH2


2 (
) .
,

,
() ,
(
)

+H2

H H

C C H C C H
C C

H H

()

 ,
1,2-
cis-1,2-,

. ,
() cis-.
CH3

CH3

CH3
H2
Pd

H
H

CH3
CH3

CH3

,

(
) .

.

 ( Markovnikov)

, :

H
C
H

CH2

HCl

H
H

CH2

Cl

 ,

,
.
, HCl 2--2, 2-2-. ,
2--3- (
).

H3C

H
C

H3C

C
CH3

HCl

H3C
H3C

Cl

H3C
CH3 + H3C

H
C

Cl H

CH3



Markovnikov, :

,

( ).
, (
).


, .

H3C

H
C C + H Cl
H3C
CH3

H3C H
H3C C C CH3 + Cl
H

H3C H
H3C C C CH3
Cl H

() ,
.
,

.
(
),

( )




.
,


+
. ,
,
( + )
.

, ,
,
,
.
,
,
.

CH3
H3C

C
CH3

CH3
H3C

H3C

C
H

,

( ),

.

CH2

+ HCl

CH3

Cl

Cl
Cl

CH2
H

CH2
H

(),
.


1,2-,
:

H
C

C
H

Br2

Br

Br


.
.
,
1,2- ( ).

H
C

C + Br
H

H
C

Br
H

C
Br H

Br

Br

Br H

,


.

,

.

 , 1,2-
1,2--1,2-
.

CH3

CH3

Cl
Cl2

CH3
Cl
CH3

H3C

Cl
CH3
Cl

 .

, 1,2-,
:

H
C
H3C

CH2

Br2

H2O

HO

H3C

H + HBr

Br

1,2-
(. ),
.

2 1,2 ().

H
C

H3C

C + Br
H

H
C

Br
H3C

Br H

H2O
-HBr

HO

H3C

Br

H
C
H3C

Br H

H2O
-HBr

HO

H3C

Br

:
1.
( Markovnikov).

C ,
(
). ,
2
.
2. .


(R), ( )
.
:

H
C
H3C

CH2

Br2
CH3CH2OH

H3CH2CO

H3C

Br

H + HBr

 2 () .

( ),

Markovnikov (-Markovnikov ).
,
(3),
().
H
H 3C

CH2 +

H
H

H H

H3C

B H

CH3
HC

(I)

BH2

2 H2C

CH2

CH

H
CH2

B
CH2

CH3
H

H
CH
H

CH3

CH3

 , ()
22
.

(I)

H2O2
NaOH, H2O

3 CH3CHCH2OH + Na3BO3
H

C,
:
1. C
, C
,

H3C

H3C

CH

H3C
CH

CH2

CH

CH2

H
B

CH2
H

2.
C ,
C.


,
- Markovnikov,
:

H
C
H3C

CH2

HBr
ROOR

H
H3C

CH

CH2Br

, .

. ,

,

,
- ,
RO. (HCl)
.

RO

OR

RO + RO

RO + HCl

ROH + Cl

,
.

1-.

Cl

H
H
+
C C
H3C
H
Cl

H C C H + H-Cl
H3C H

Cl

H C C H
H3C H
H Cl

H C C H + Cl
H3C H

, .


,
C,
.

,
C,
,
.

Cl

Cl

H C C H

H C C H

H3C H

H3C H

 .
1,2 :

KMnO4
1.OsO4, 2. NaHSO3

H3C

CH3

1. CH3COOOH
2. NaOH

OH

OH

CH3 CH3

OH

CH3

CH3 OH

1,2- cis-,

1,2- trans-.

 .
,
.

, ,
:

R1

R3
C

R2

R4

O3

O O
R1 C C R3
R2 R4

R1

O O

R3
C C
R2 O R4

R1
Zn
CH3COOH

R2

C O

R3

R4

C O

.
, ,
.



.
R2=R3=R4=H

R1

C O +

C O

H H
R3=R4=H

R1
C

R2

R3
C

R4

C O +

C O

R2 H

1. O3
2. Zn/CH3COOH

R1

R2=R4=H

R1

R3
C O +
C O
H H
R1

R3
C O +
C O
R2 R4


.
H

H
H

O
C
CH3

+ H

C
H

OH

CH3 H

H
H

CH3 H

O
O3
Zn/CH3COOH

Cl

H
C

CH3 H

KOH

H2SO4

Cl
C

H2/Pd

CH3 H

HCl

HO
H

CH3 OH
HO HO
H

1. CH3COOOH
2. NaOH

H
C

H3C

KMnO4

H2O/H

HO

CH3 H

Br2

HBr,
ROOR

CH3 H

H
H

CH3 H

1. BH3
2. H2O2, OH-

Br

H
H

H
H

Br
OH

CH3 H

Br

Br2/ROH

CH3 OR

CH3 Br

 trans-4--2-
1

Trans-2-

 2--4--1-

1-

2
4

2
4

Cl

3
4

1
2

5
6

4
2

H
2

3
1

IUPAC

(R)-3--1-

(R)

2
3

6
1

IUPAC

1-

 :
. trans-1-

1-

.
. ()-3--3-

5
()-3--3-:

1-

2
4

-3

(). ,
.

,
3--2-

1
2

3--2-

. 2,4--1,3-

1
5

2
3

. 1,3-1,3-,


.

4
3

5
1


.
:

. 1- +
.

,
.
,
:

Br
Br2

+
Br

Br

Br

. cis-2- + + NaOH 10 C


trans ( ).

+ Cl2 + NaOH
Cl

OH

Cl

. : 1- + 3 , : Zn/CH3COOH
.
, ,
.

O
1. O3

O
H

2. Zn/CH3COOH

 3-2- .
:
. Br2

Br2

Br

HO
r2 2.

1,2-.
.

HBr

HBr
Br
Br .
Markovnikov
C.


3- HBr
r .
. 3-
, -Markovnikov
(HBr/ROOR)
Markovnikov (HBr) .
Br

HBr
ROOR

HBr

Br