ALCOHOLS, PHENOLS, & ETHERS

" Name Reactions

1) KoLBE's REACTION:
OH ONa
COOH
NaOH
(i) Ht
"3-HyDROXY&ENZO1GACD6)
PHENOL o SALCYLIC ACD
" O- Mydroxybenzoc ad
ONG

reachve owards E sub. reac .:

xeacls eveu with tak ekchoplule k co
2) REIMER - TIEMANN REA CTION_:
ónat CHO
CHUa + af NaoH CHd, Na0H

Intermedat
OH
(Sub Sh hieol CH6
enzal chlonde)
SALICYLALDEHYDE

SON
3) WILLIAM SYNTHESIS: (Sy mech)
" Reachcn of an alkyl hade ith Sodion alkoxicle
sodum phunokIde o fem ether.
Conveuerl mehod to prepare
e hers

ONa
+ NaI

When ° alkyl halile å used , ocCus, ether i fomd

when 29 eliminahon &S, oCtu, eHr
aie femed
ka alkn o(Cues, togekes
a/kene ç fore
 H,O)
B
H (H-BH,),
Markoynikov'
add s Anti-
alcohol yieloExcellent
d
(BHs), OiBorare bsed Reogaut
0XLDATION& HYDROBORA
TI-ON )
REACTIONS TANT TMPOR OTHER X
phenone
p-mehoxy
accl-
coCH Acylatom
coy Coc! CH,
+
Anisole
Major toluen
Mehoxy o- AICg Anh
CH3 AEylahen
+
(rnjor)
Acylahon
COCI CH,
Phenal
Akylahja
Cl
CH,
REACTI
:
ON FTS CRA FRIEDEL- 4)
2.) DOW'S PROCESS ÖNa
623k
300 ad

fsom CUMENE (SOPROPYL BENZENE )

CH3
OH
H-c-0 -0-H
+ co CHs
Cumene Acetone
(byproduct)

4) hep" ASPIRIN
COOH COOH

+ CH, Co0H
sabeylie atud Aceiylsabcyhic acd
(ASPIRIN)

5) OXI DA TION OF ALCOHOLS:

R-OH Bcids Aocdfed kMnO.,

’ Alcohols
PCC
, CHO

(PCC ’ cdinium cAlechromate)

) 2° al cehsts to ketones

-CH-0 Cro, C=0

Chyomuc anhydude)
 3° aleohots ae reSistant to oxi.
C-c bonds kaypens
eith Jeney zo.f CC- aoms.

OH

+ co, 4 H o

OH

6) REACTION Cu at 573K (oxidahon)

to aldehydles
RCH, OH RCHO
573 K

alcohol to ketone
R- H-R
S731
aH

-C04 Elia1naHen f
o)

3° alohod to alkne.
PHENOL wTH
) OH

Br 38r
Broune
in CS, Lyater BY
2,46-Iribonspheno
(Mayer)
inotcn white Ppt.
 8) oxdaton ophenol hor t. chromiC atid
Na, (, O4
(onjegaled dikdu)
77777 Tn the presenee of air phenals ane
benzoquinou

dark colouacd mixhues Conlaird qui nones,

alkyl halide u vsed in William Son Syntheni

al kene i major product as Eliminahon domnates
Substhehon.

BY
(Bare)
3° Brorce
nucleephule
Abshaeli H)

halide Used then ethes S

C, - c oNa

Nuchepbil
19) REACTloN ETHERS HX

(S mech)
4u case of wnsyrmsh tal ethers Alkyl hali ole i
lowtr alkyl gopo ue to _les
alaays fomud
steric hin deance (This
alkyl guag)
+ H T
CH, O-C, C's CHg -7 + Cy C, OH
 But t ne of he alkyl
fo leued alkyl hali cle e fomed fom 'alhyl p
CH3
CH
CHs

In Case
Phenol
bond b/a moe shbk/shong du to sp
deuble bond character
Ltemediale +

mehyl phnyl OXor0m

oH

HI CHg T

1) REACTIoN OF PHENOL wITH HNO

OH OH
Dil. HNO3
OH

(Majr)
OH
Conc. HNO3

Picric Aci e
2,4, 6- Tri hibep henet
 MECHANISMS ; Catalyed
hep f alcoheb by acidlc hyation of alkenes
H+
+ H, o
" MECHANISY: 3 steps
STEP 1: Potonaion ot alkene to fora Canbocahian
byby elechophi lie atack o H,ot
H
H

H + H, O:

STEP Nucleophihe atlack of water n ce

H

STEP 3 : Dep rotonahon an alcohol

H

-C-C
/

a 2) DEHYDRATI ON OF AL COHOLS TO FORM ALKENES

H, S04 CH, =0i,
443k

Auchuly order

" MECHANISM:
STEP 1 - Formahon ofa proonafed alcohol.
o-H fasl
H H
 STEP 2: Formahan a RDS.
3# ` Sbuest slep so Rs

STEP 3 fosmmaHon ot ehen by elimination f

protm.
H
H

Alkene

3 pehydration of alcohols to fom ethers.

CHz -C -OH
Hpoy 43K
Suitable alcohols as it fo llows S
mich., So Steric hinderance Jess
2° 3° alcohols Undngo s mech to fem alkenes.
&imolecular dehyorahon fer tle
eher
miahui
7o ceparalt
R OH + RoR t ROR eoe
4/3 k

MECHANISM:
STEP : Protenahion

Protonatc albohol
STEP 2 :Nuc leophibc attack of gnd alcoh ol
molecule,
S low

H,0
 STEP_3 Deprotonation (Remoral of aa H)
+

ETHER

(4) RencT/ON OF ETHER Conc. HI HBr

CH, -0- CH C CHy -I

" ME CHAN (SM:

STEP 1" Pro lonahon of eHer
+ H-I
CH, 0- -
OXonium ion
STEP 2 Attock of I as Nucleophile by S2
S mech
alky gups only)
+

I +

CH-I

When HI s n excess vsed

e hand zeacli n hir coith HI Zo

H- IT
exce ss

+ HO

DIS TINCTION y°2, 3° ALCOHOL

LUCAS TEST:
Alcohol bealil Lucas zeageul (ejimola
veochon, alkyl chlon dles -femad aofich kcing
insotuble resull in tunbidity oslothiay
Alcahol
Zn C!,
Alkyl chlaide t HO
 Turbi obi by
appeans only heating
No tunbidily ppeas Uncle normal Condiheuse.
2° AL COHOL
3° Turbidiy appeas n s- lo muñ
ALCOHoL
imanediakely
VIcTOR MEYER TES
ToT n NCERT, So not for bogrd)
° alohot Bloo
RCH, OH HI Ag No, HONo Naon kod
Co laur
Nihohc ad
2° alcohol
HI HOND
RC-NO
21
NaoH B/ue
NO Cu louy
Pseucdoribel
3° al cothot
HI
HONO No ren nqon
Goloules
3) IODOFOR M TEST: OH

Any alcohet ontaining the

fest ve
gire ye ikbw prt of cHI,(Todefom)
pon haahing cwtt 9 Na OH or a, Cog
OH
+ 41, + 6NaOH
CHI, t HCoONG
Ethanol H
Jodofe
Ye llow Ap 5Na

No ea w

*" Bo it younsel!:
Gut of Pentan - 2-ol R Penan -3-ol whch coill ge Todfon
fest posihve Jb Cham cqu
4) TEST FOR PHENOL : fe CI, Teot
Fey 343K, Fe (oçts)e + 3H +t 34C0
Phenol
VIolet complex
 fe Cla + 3H
neubal

Violel Conplex
* ACIDIC NATURE Of PHENOLS:
Phenols are more aidic than han alcohols
alohols because :
(0 -oH 9p in phenot cd cnectly attachud o
sp' hybidise d c of ben Zme hch e' densiky
0-H bCud
(i) phenokide
Atabihsed by XOsonQnee Hhon phenol as in phenol Hhere
Chasge sepaahe
Refer to Shuctues NCERT
Phenoki de icn theno) book,

i) su sobstihulid phoned, an e'aithdrautng teyp (ena)

wtile an

Aadc streuçdt orderi

OH
NO

0-NITROPHENoL STEAM VOLATIL6

o-Nihophenf p-nibophenof
fhe -or Hho -para L`omess Can ke
separakd by
SHam
dusillahonr
nibqphanal Steam ylahle de
to IN TRAM OLE CULAR H- 80NDING wtile
p-nilbpkanl Jen volahle de fo
infermole aalar Whandu
 OTHER ToPICS TO BE DONE FRON, WCERT
Nomen clature i- ABcohels, phenol.
phenos, ko chers.
Classifkcatio of cohols
8huckeu of funthinad
Keparation mahodlo ef alchok, pheroh, k churs
Physical preperhes ef alekos <phents, 'chus
ees
Comscialy
Chenica
inspo lont alkekolk - oyoy, ,sou
leachos of aletels, phenols k ehars
f Phonols &ehors,
AU NCERT
DiSTINCTI 0N ALCOHoL BPHEoL
TEST ALCOH oL PHENOL
Litmus Test No efte Tusus blue lihn0s red
No YIo le colouraho
reach No reac
ferms orange /yelks tokusd azo lyes
No read A whlE Apt of 34 6- bibronphsnal
THe REDUCIN G AGENTS (k their achio)
DOES NOT AFFCT BOUB LE BOND
y CH,-4= HCH, OH
CH-C= CH - CHO
Ha/Ni
Roduce dlouble bond aloo

REDUCTION By NabHy

NaBHy HO
No vedn of

redutes bott