METHODS OF PREPARATION FROM HYDROBORATION

OF ALCOHOLS OXIDATION FROM DIAZONIUM SALTS METHODS OF PREPARATION

FROM CUMENE:
OF PHENOL
CH3 OH
CH3-CH=CH2 +(H-BH2)2 CH3-CH-CH2 N ≡ NCL OH CH3
From alkenes, by acid Catalysed Hydration: CH C–O–OH
H BH2 NaNO2 H2O CH3 O3 H+ + CH3COCH3
+ N2 + HCl DOW'S PROCESS:
+ HCl Warm
H CH3 H2O
C C 
+ H2O  C C (i) 623 K, 300 atmPhenol
CH3-CH=CH2
Chlorobenzene+ NaOH→
(ii ) HCl
NH2 Cumene Cumen
H OH CH3-CH=CH2
(CH3-CH2-CH2)3B (CH3-CH2-CH2)2BH Aniline
Benzene Hydroperoxide
Diazonium salt
H +
 CH -CH-CH
eg. CH3-CH=CH2 + H2O  CH3-CH=CH2
3 3

OH 3CH3-CH2-CH2-OH+B(OH)3
Colorless crystalline
Propan-l-ol FROM BENZENE SUPLHONIC ACID solid or Liquid

SO3H OH PHENOL PHYSICAL PROPERTIES

Reduction of Aldehyde, Ketone and
From Grignard reagent
Carboxylic Acid Oleum (i) NaOH Higher boiling point due
(ii) H+ to Hydrogen Bonding
pd
R − CHO + H 2  → R − CH 2 OH δ− +δ
C O + R + MgX C O Mg X CHEMICAL PROPERTIES
Halogeneation
NaBH
RCOR′ 
4 → R − CH − R
H2O OH OH
OH Electrophilic Aromatic Br Br

RCOOH 
(i) LiAlH
(ii) H O
4 → R − CH − OH
2
2
Mg(OH)x + C OH
ALCOHOL, PHENOL substitution + 3Br2 + 3HBr
R
AND ETHER Br

Nitration
PHYSICAL PROPERTIES OH OH
ALCOHOLS Conc. NO2
NO2 NO2

HNO3
NO2
Soluble in water M.P. and B.P. ∝ Colorless with
ETHER 2,4,6-Trinitro-phenol
due to H-bonding Molecular mass M.P. characteristic Structure
and B.P. ∝ s smell R-OH Structure

where R = alkyl group R-O-R′

Reimer-Tiemann reaction: Treatement of
CHEMICAL PROPERTIES where R and R′ can be phenol with -
same or different alkyl CHCl3 + KOH O Na+
Reaction involving Acidity: Due to the presence of group CHCl2
OH
cleavage of -OH bond. polar-OH group. CHCl3 + Aq. NaOH
OH ONa R
R
R CH2OH > CH-OH > R C OH CLEAVAGE OF C-O BOND ELECTROPHILIC SUBSTITUTION
R Intermediate NaOH
+ NaOH + H 2O 1° alcohol
R 2° alcohol
R − O − R + HX 
→ R − X + ROH
(I) HALOGENATION -
O Na
OCH3 CHO
R − O − R′ + HX 
→ R − X + R′OH OCH3
CHO
OCH3 Br OH
Esterification H+
OH Br2 in Ethanoic Acid
H+ +
 ROCOR′ + H 2 O
R − OH + R′COOH  OR
H

+
 ROCOR′ + R′COOH
R − OH + (R′CO) 2 O 
CHEMICAL PROPERTIES + H-X + R-X Br Salicyaldehyde

Pyridine

R − OH + R′COCl  
 ROCOR′ + HCl For Tertiary Group:
CH3 CH3 (II) FRIEDEL-CRAFTS REACTION
Oxidation Phenol
OCH3 O
CH3 - C - OCH3 + HI → CH3OH + CH3 - C - I OH OH
Dehydration Reaction Oxidation OCH3 CH3 H3CO
AlCl3 Na2Cr2O7
CH3 CH3 + CH3Cl +
H O H2SO4
H+
C C 
Heat
→ C + H 2O Oxidation [O]
H3C
R − CH 2 OH → R − C = O → R − C − OH O
Aldehyde Carboxylic Benzoquinone
H OH Acid PREPARATION OF ETHER
Victor Mayer Test

Primary Alcohol Secondary Alcohol Tertiary Alcohol

Williamson Synthesis By Dehydration of Alcohols
1) P+I2 1) P + I 2 1) P+ I 2
CHEMICAL TEST R − CH2 − OH  → Red Colours – + 2CH 3 − CH 2 − OH →
2 4 H SO
C2 H5 − O − C2 H5
2) AgNO2 2) KOH → No Colours
AgNO NoReaction 
R3C − OH →

: :
FOR ALCOHOL 2) AgNO R2CH − OH  → Blue Colours R − X + R − O − Na 
→ R − O − R + NaX 413 K
3) HNO

:
3) HNO , KOH 3) HNO , KOH