A (ao)

H3COH (MeOH)
o

H3CCH2CH2OH (PrOH)

H3CCH2OH (EtOH)

1-o

eo

1 a
1

3
4

OH

1-o
(n-)

3
2

OH

OH
2,2--1-o

2--1-o
(i-BuOH)

OH
4

(H3C)2CHOH (i-PrOH)
2-o
()

OH

2-o
sec- (s-BuOH)

OH

cis-2-
o

OH
3

trans-2-
o

HO

Et

3 a

2--2-o
terc. (t-BuOH)

2 a

1-eo

 (a)
3

CH2OH

OH

H2C CH CH2OH
2--1-o
(a )
OH > =

aromatian

2--1-

o
( )

Ke-e

OH

H2C C OH
H

E o

H3C C O
H

OH

OH

A ?
IUPAC-.
OH

Je

OH

OH

OH > NH2

NH 2

3-a-2-ol

4--2-on

CH 2 OH

HO

OH

1,2-
(e)

CH 3

2-

2-

OH

OH

OH < CO, CHO, COOH

HO

3
2

OH

OH

O
104
H
H

d
d+

108

112

d+

d+

CH3

d+

Tk
R
d

d H
H O

C nH2n+1OH

n>5

H
O
R

H-

K-

A

R O H

+
H ( .)

R O H

( )

R O

+ BH

B = NaNH2, Na, RMgX, BuLi

K
H3C O H
pKa =

H5C2

15.5

O H

pKa = 15.9

NaNH2

H3C O Na

Na OH

H5C 2

NH3
pKa = 35

O Na

H2O

pKa= 15.7

1 2

1 2 3

CH3OH > RCH2OH > R R CHOH > R R R COH

R1

C O H

+I e O-H

R
C

C O H
2

3 a
OH

- I e

pKa

pKa

H2O

15.7

HOCl

7.5

CH3OH

15.5

ClCH2OH

14.3

CH3CH2OH

15.9

CF3CH2OH

12,4

(CH3)2CHOH

17.1

CF3CH2CH2OH 14.6

H2O2

18

H
Cl

C
H

Me
: - =
H3PO4

RCH CH2

HOH

300C

RCH CH3
OH

: 1. hidroborovanje
2.O

CH3

BH3/THF
H2O2, OH

CH3

OH
trans-2-

: 1.o =
2.

RCH CH2

[H2O2]

R
H2O

RCH CH2OH
OH

Ka 1- :
a) 1-
b) 2-
c) 1--1,2- trans-
d) 1--1,2- cis-

Ka 2- :
a) 2-
b) 1- ( )
c) 1--2- (
Gringard-a)

O
O

Cl
Mg

CH2OH

H3O

Et2O

H3O

H3CC CH

BuLi
THF

THF

H3O

OH
1-

 e Gringard-o
3 a

2 R MgCl + R

O MgCl

O
C
OEt

R
MgClOEt

H3O

OH
R1

R
R

- e--
2 a. Koj?

 je

O
RC

i LiAlH4
1

OR

1a

1a

OH

O
2

ii H3O

RCH2OH

LiAlH4/Et2O
1

ii H3O
H2/Pt

CH R

2 a

Cl NaOH

OH

H2O

a
O

NaOH

H3C
OCH
CH 3

RCHCH 3
OH

CH3COO Na

 C-O

a
R

(SN1, SN2,)

OH

( SN )

CH3OH > RCH2OH > R2CHOH

3> 2> 1

SN2

<<

R2CHOH

<

R3COH

O-H

SN1

ROH
jo

R Z

Nu

R Nu

Z

( )

R OH

OH

>>

HOH

X
H

<<

R X

.

HX

Ka ?

SN

RCH2OH

HBr

RCH2 OH

Br

RCH2Br

H2O

o .

KBr/H2SO4

CH3
HBr
H3C C CH2OH
CH3

CH3
H3C C CH2 OH2 Br
CH3

Br
H3C C CH2
CH3

CH3

H2O

SN

H3C C CHOH

HBr

H3C C CH OH2

H CH3
3--2-

CH3
H3C C CH CH3

CH3

CH3

H2O

H CH3

CH3
H3C C CH CH3

H
H

2 3 ()

Br

CH3
H 3C C CH

CH 3

H Br
2--3-

CH3
H3C C CH

CH3

Br H
2--2-

 - PBr3 (PCl3), PX5 i P/I2

(PI3)
PX3
ROH

PX5
P/I2

ROH

Cl

O
S

RX
X= Br, Cl, I

RCl
Cl

SO2

HCl

 (e H2O )
OH2

OH

H2SO4

HSO4

CH3

CH3

CH3 130C

1-
(Zaitsev )

O
HO Cr OH
O

HO R

HO Cr OR
O

H2O

H2O

1. e :

CH2ONO2
HCONO2

HO P OR
O

CH2ONO2

2. e :
O
C2H5OH

CH3C

ArSO3H

H2O

CH3C
OC2H5

OH

RSO3H

O
e-

RSO2OR

O
S OR
O

O k (ili nekog

e o )
C-O je

O
CH3C

[O]

CH4

CH3C

Cl2

CH3Cl

HCl

OH

O o C-H

R
R C H
O H

R
[O]
H2O

R C
O

C 2H6

H2C CH2

HC CH

O :
RCH2OH

[O]

[O]

R C

O
R C
OH

1 (PCC)
o , e (KMnO4, CrO3/H+)

PCC

tBu

CH2OH

CH2Cl2

tBu

CHO

94%
PCC =

N
H

ClCrO3

R CH2 OH

KCr2O7
H2SO4 /H2O
(ili KMnO4)

R C OH

2
(K2Cr2O7/H2SO4, CrO3/H2SO4, PCC/CH2Cl2)

R1
R C OH

[O]

R1
R C

a-

R3C-OH

[O]

1 a (PCC)
o , (KMnO4, CrO3/H+)

R C H

PCC
CH2Cl2

R CH2 OH

KCr2O7
H2SO4 /H2O
( KMnO4)

R C OH

2 a
(K2Cr2O7/H2SO4, CrO3/H2SO4, PCC/CH2Cl2)

R1
R C OH
H

[O]

R1
R C

o
NAD

NAD

 :
H

1,2- ( )

KMnO4, H2O. 0 C

OH

pKa = 7

OH

OH

sin- =

OsO4/THF
25 C. 48 h

OH

[3,3,0]-1-o-2-o

cis-1,5-

[3,3,0]o-2-

anti- =
MCPBA
CH2Cl2

O H2O/H

OH
OH

1.3-

H2C

CH CH2Br

HBr
ROOR

BrH2C

CH2 CH2Br HOH/OH

HOH2C

CH2 CH2OH

1,3-
1,3-

SH

CH3 SH

SH

HSCH2CH2CH2SH
1,3-

Ka SH o IUPAC-

Ka SH IUPAC-

CO2H
H2N C H
CH2SH
3--2-

HSCH2CH2OH
2-e

- :
a) t.k. o o a
b) K o a

RSH > H2O => CH3OH > 1 > 2 > 3

pKa 9 - 12

15

15,7

RX
NaOH

RS H

CH3 Cl

RS CH3

NaCl

--

O
CoASH
A

CH3C SCoA

a- A je

2 RS H

2 H,

2e

2H

2e

RS SR

CH3SH KMnO4 CH3SO3H

 ()

O
H3CS CH3

H2O2

H3CSCH3
O

H2O2

H3CSCH3
O