CHAPTER

11
Alcohols, Phenols
a n d Ethers
1 1 . 1 Cla ssif icat ion
11 .2 Nom enc latu re
11 .3 Stru ctur es of Fun ctio nal Gro
11.4 Alco hols and Phenols
11 .5 som e Com mercially Imp orta
nt Alcohols
J
ups 11 .6 Ethe rs
To pic wis e An aly sis of Las t 10
Years' CBSE Bo ard Qu est ion s (20 20- 201 1)

32 ■ \SA
- 0 SA
28 ~LA I

1.., 2-t
C:
~ L;\ rt

.2
i::, 20
......
,:r-
0 16
...
A
E 12
::,
z
8

4 ~---- ·--- ------- -- -

0
ti.I IL:? 11.3 11.5 11.6
Topi c-- +

.
Max im um lOld l welg htag e ls of
Alco hols and ►► M axim um SA ~nd LA I type questions were
0

asked from Alcohols and Phenols.

Phenols.
.
►► M axim um VSA type que stio ns were aske d from
Alco hols and Phenols.

- - - - - - - - 1 (QU ICK RECAP )

s alkyl alcoliol. According to
are nam e d 3 d • tk ols'
ALCO H OLS LUPAC system, alcobols arc caUc a an '
_, ~ mu la : Alcohols are the hyd roxy •
CD Gener.u. ior . raJ formula
b replacing •-e' of alkane by -of.
Y
derivatives of alkanes having gene R OH the O-atom
C) Stru ctur e : ln alcoho_
ls, - t,ed lo C-atom
e" ll1,, + 1O I L of hydroxyl group is altac
CD !co hols
Nom enc lature : 1n co n:unon system, a
 by a s,igma (_CJ~ bond
formed by the overlap
of sp bybndtsed or G) Classification : Al
bital of C-atom wi cohol~ are das~1fied
lh
as mon~hydric, thh
~
5P
1
hybridised orbital of ydric, lrihydric and
O-atom. polyhydnc alcohols
depending upon the
R l~<r H number of hydroxyl
(- O H ) group~ pres
m the molecule. ent
\lonohydnc alcohols
Al co ho ls
1° Alcohol 01h,·dric Trihydnc
2 Alcohol CH -C H Polyhy<lric
CH iC H2 0H 1 -C H , .
CH ,0 H CH 20H
Ellwl.ilcuhol
I I I CH ,0 H
OH
lsopr,,p,·I alcohol
CH 20H O l0 H \ -
a 1,c11 2c1':PH (CTI0H)
Eth, Im . gh rul
I 4
11-rropyl alrohol
CH C H ,-O H
I .
CH 10H I
Vin)•ltc CH = C H -0 1
3° Alcohol CH - C
Cli"'fin<' C.l )m ul CH20H
2 H -C tt3 CH , •l~ -ne -1. 2._ '\-
alcohols 1 "<,rl,it"I
(Ln,ubl~l I
OH
. I - in.,11 (lk uh vJ nc
C H c0 II alroh<ill
la' Butyl •k,-h<il
Pn ,p tt- D- d1 nl
Allylic .ilcohols CH CH3
~= C H -C H ~-
. - 0H
P«,p-2-.,n-l-<.,I
C H ,= C H -C H -C
- I H I
C ll, =C H -C
3 • I -C H 3
(]• ) OH
0 11
2-\lrthyltnn-:W..-?...&
O il (J' )

'
C H -C H3
Bcn7) he alcohols

114.-nzyl mo ho l
(l"l1<•1whnt·th•n.>I)
6 I
l-M1cnvl~th,lllol 2•Ml<-nylprop•n-2-ul
· wi 12')
(31

0 Pr ep ar at io n : ► From ca rb on ,\ com
► Fr om alkenes: pounds :
- By redu ction of aldeh}d
- By acid catalyse es and kelones :
d hydr at io n :
2~ RCH 20H
RCHO + H
CH ,CH = CH, -t H ,0 H"
. - • ~ CH 3-CI H -CH3 RCOR' :-;~Bil, > R -C
H -R '
OH I
By hydr ob or at io n-ox 01-1
id at io n: - By reduction of carboX
) lie ad ds and
C l i CU =CH + (H esters :
3 1 -BH2h i (I) LiAlH~
CH 3-C H -C H 1 RCOOH (n l > RCHPH
I 1120
I -
H BH 2 RCOOR' W iH 2o
> RCOOl l + R'Ol l
CH 1Cll = CI I,
(CH CH CH h,BH From Grignard reag
3 2 2 - en ts :
R'
CH,CH=CH2 (CH3CH2 C HB2 ): RCHO + R'~tgX H!
J· O > R -t H -O M
gX
H.0 lH10
3CH CH CH 0H-'- B(
3 2 2 O H)3 oH R'
Prop.in- I-t1I
Mg(Ol l)X + R -CI H
-O H
 R' Lucas tesl : Lucas reagenl is a solution of
RCOR+R'MgX ~ R-t-OMgX cone. I ICI with anhyd. ZnCl1 .
I With Lucas reagent,
R
Primary alcohols- No cloudiness
f' !lip Secondary alcohols - Clo udiness in 5 minutes
Tertiary alcohols - Cloudiness immediately
R- C - OH + Mg(OH)X
I - Reaction with phosphorus trihalides :
R
0 Physical properties : ROH+ PCl 3 ~ RCI + 1-1_,POJ
► Physical state : Lower alcohols are colourless - Dehydration :
liquids with characteristic smell while higher 11 2SO4
alcohols are colourless, odourless waxy solids. C1lls01 l 113 K > CH 2=CH 2 + H 20
► Solubility : Solubility of alcohols in water
is due lo their ability to form hydrogen
OH
J 85"- H3PO➔
bonds with water molecules. The solubility Cll 3CHCH 3 440
K > CH 3CH=CH2 + H2O
decreases with increase in size of alkyl
groups and solubility increases with increase
9H3 200u1I3P04
CH 2
II
in branching and Lhe order is 1° < 2° < 3°.
Cll3- C- OH 358 K >CH3-C-Cll3 -+ llzO
► Boiling points : The boiling points of t113
alcohols increase with increase in the number 1hus, the relative ease of dehydration of
of carbon atoms as van der Waals' forces alcohols follows Lhe order :
increase and Lhe boiling points decrease
Tertiary> Secondary > Primary
with increase of branching in carbon chain
due to decrease in van der Waals' forces with - Oxidation :
decrease in surface area and the order is H OH
1° > 2° > 3°. RCH 2OH~R-t=O~R-t=O
Chemical properties : Alcohols react both Aldehyde Carboxylic
acid
as nuclcophiles (when the bond between
0- H is broken) and elcctrophiles (when RCH20H c r0 , or Cu/573 K RCHO
the bond betwe,cn C- 0 is broken}.
Reactions involving cleavage ofO- H bond: CH3CH=CHCH20H Pee >
►
CH 3CH=CHCHO
Acidity ofalcohols (reaction with metals) :
2ROH + 2Na ~ 2RONa + H, R-CH-R' Cr0 3 or Cu/573 K R-C-R'
Sodmm - I II
olko:udc OH 0
sec-akobol Ketone
The above reaction shows that alcohols
are acidic in nature. CH3 CH3
- The acid strength of alcohols decreases in CH - 6 - 0H ~; K> CH3-t=CH 2
the following order : 3 I 5
CH3
R~ R~
R-+-CH, OH > CHOH >> R-+-C-OH CD Some commercially important alcohols :
- RI"" w?f" ► Methanol (wood spirit) : Tl is produced
Primary Secondary Tertiary by catalytic hydrogenation of CO in the
Esterificatio n : presence of ZnO - Cr2 0 3 as catalyst at high
R'OH + (RCO) ,O or R'COCI ~ RCOOR' temperature and pressure.
► Reactions involv ing cleavage of C-0 bond : ZnO-Cr103
Co + 2H 2 200 300 C O
otm. 573 673 K H3 H
Reaclion wilh hydrogen halides:
/\ nhyd, ZnCl1 ) - Methanol is a colourless liquid and is
ROH + I-IX t:. RX + H20 highly poisonous in nature.
 Ingestion of small quantities can cause OH OH
blindness while large quantities can cause ~OH TroYyOII
death.
It is used as a solvent in paints, varnishes UoH rroVoH
and for making formaldehyde. OH
Ethanol : It is commercially manufactured Py rogalllll He~aplwnol
► (Tnhydrk) (Polyhyd ric)
by using fermentation of sugar present in
molasses, sugarcane or fruits such as grapes. 0 Preparation :
lnvertase ► From haloarenes :
C12Hu 0 11+ H20 > Ci,111206
Glucose Cl o -Na+ OH

C61I120 6 Zymase 2C2H50H + 2C02

+ C6 H120 ~
FruclOM'
V
A + NaOH 613 K
300atm
> 0
V J.!f4 0
V
Glucose Ethanol
► From benzencsulphonic acid :
Ethanol is colourless liquid and is used
as a solvent in paint industry and in
preparalion of a number of carbon
compounds. 0~ r/
Olcum ) 6~S03H

r/
(I) NaOH )
(Ul Ir
6~
OH

,,,../
Commercial alcohol made unfit for
► From diazonium salts :
drinking by mL'<ing it with copper sulphate
and pyridine, it is called de11atured NH2
N;c1H, O
A
PHENOLS
alcohol.
V +HCI
~ :tN02

6 W o;m l
C) General formula : Phenols are the
compounds in which hydroxy (- OH) group
Aniline Beuzeoedinonfom
chlorid., AOTT
is directly linked to aromatic ring having V + N 2 +HCI
formula, C6 H 50H. From cumene :
►
C) Nomenclature : The simplest h)'droxy
derivative of benzene is phenol, also called
rnrbolic acid. It is its common name and also
an accepted I UPAC name.
C) Slructure : In phenols, the - OH group Cumene Cumene
is allached to sp2 hybridised C-atom of an hydroperoxide
aromatic ring.

6
OH

~Qp CH 3COCH 3 +
~H Physical properties :
C) Classification : Like alcohols, phenols are
Physical state : Phenols are colourless
also classified as mono and polyhydric phenols.
crystalline solids or liquids.

6 &OH&OH ¢
Phenol
(Monohyd ric)
OH
►

►
Odour : They have characteristic phenolic
odours.
Solubility: Like alcohols, phenols are soluble
in waler due to the formation of hydrogen
Calechol Resordnol H ydroquinone
bonding with water.
(Quinol) __,,/
Phenols are less soluble than alcohols due
to large hydrocarbon (benzene ring) part.
 - Phenols are soluble in alcohols, ethers ► Electrophilic aromatic s ubstitution :
and also in NaOJ I. Nitration :
► Boiling points: The boiling points of phenols
OH OH

C)
are much higher than the corresponding
aromatic hydrocarbons and haloarenes due
to inlcnnolecular hydrogen bonding.
Chemical properties :
6 Dilute 81'0 3 ~ N02+ ¢'-::
v
o-:llitrnphenol
2
NO
p-Nltrophenol
&

► Acidity of phenols : Phenols are weakly

acidic in nature due to polar 0 - H bond OH
direclly allached to sp2 -byb,idised C-atom.
They turn blue litmus red and react with
alkali metals and alkalies ro fonn their salts.
- Phenol is weaker acid than carboxylic
6 cone. HN03
cone. H,S0 1
02NhN02
y
N02
:z..t,6·Trin.itrophenol
acid. lt does not react with sodium
(Picric ncid)
carbonate (Na 2C03) and sodium
bicarbonate (Nal IC03). - Halogenation :
OH
Phenols are more acidic than alcohols
which can be explained on the basis of
resonance.
Electron withdrawing groups increase
6 Br2 inCS 2
273 K )

Minor
the acidic strength of phenols. Maior
- Electron releasing groups decrease the

6
OH
acidic strength of phenols.
Reaction with metals: + 3Br2 HO
2 > Br* B
I r
~
OH ONa

2 6 + 2Na ------> 2 6 + H2
► Kolbe's reaction :
Br
2,-1,6 Tribromophenol

6
Phenol Sodium phenoxiJe
OH ONa
In addition to this, phenols react with
aqueous sodium h ydroxide to form sodium
phenoxides.
OH ONa
6 :-.laOl::I )
I A
(il CO2 )
('.)
" H"
2-llydroxybenzolc 3cid

6 + N,011 ------> 6 + H 20 ► Reimer-Tiemann reaction :

(Salicylic acid)

l
6 OH o·N
(rc11c1]
l
Sodium phenoxide t:

► Esterificatioo : CHCI, Hq. N,OH

COOH

V
~ OH
+ (CH3CO)zO
H+
) lnlcrmcdiute

}.:,10H
S;tlicylic ncid
COOH OH o-Na+
~OCOCH3
V +CH3COOH
CHO H1
~
&CHO
~
I
Acctylsalicylic acid
&
(Aspirin) Salicylrudehycle
► R~~ion of phenol with zinc dust :

►
6
Oxidation
+Zn - o +ZnO
approximately in a tetrahedr I

~D
0
R~
a arrangement.

Classification : Ethe~ can be cl ·ri d

. ass11e

6 0l-:J Na Cr o ~s symmetrical or simple ethers h .

2 2 7 formula, R- 0 - R and u . avmg
,.,.,
... I H2so~ ➔ . nsym.metrical or
rruxed ethers having formula, R - 0- R'.
Preparation :
llenzaqulnone From alcohols by dehydration :
► Tes t :for phe n ols :
2ROH H2S04, 4 l3 K
F,erric chloride test : Phenol gives violet ROR
► From aU..-yl halide :
colour wi th neutral FeCI 3 solution.
OH R- X + RONa _:ax ➔ ROR

6 6 + FcC13 ~ 31-f' + IFe(OC6H,).J'- + 3HO

(violet complex)
(Williamson synthesis)
Williamson synthesis can be used to
prepare ethers containing 2° or 3° alkyl
groups thro ugh SN2 mechan ism. In this
Br omine water test : Phenol gives white
case, Lhe alkyl halide must be 1°. Tn the
ppt. with Brr water due to the formation
of 2,4,6-tribromophenol. case of2° and 3° alk-yl halides, elimination
lakes place. ll cannot be used 10 prepare
OH 0 1L diary! ethers.

6
~ 1 + 38 r2
tr,o
➔
BrhBr
y
Br
+3HBr
Dehydration of alcohols for the formation
of ethers follows Lhe order: IO > 2° > 3°.
Physicul properties :
Physical state and odour : Dimethyl ether
(white ppt.)
ETHERS and ethyl methyl ether arc exceptionally gases
at room temperature while ail other et.hers
General formula : Ethers are Lhe compounds
are colourless liquids with characteristic
having general formula, C,,H 2,,+20 ; where, ethereal smelJ.
n is a lways greater than 1.
► Solubility : Ethers are soluble in water to a
Nomenclature : Common names of ethers certain e>..1:ent due to hydrogen bonding.
arc derived from the names of alkyl/ Solubility decreases with increase in
aryl groups written as separate words in molecular mass.
alphabetical order and adding the word Ethers are fairly soluble in aU organic
'etl,er' at the end. If both the alkyl groups solvents such as alcohol, chloroform,
are lhe same, the prefix 'di' is added before benzene, etc.
the alkyl group. According to JUPAC system ► Boiling points : Ethers have lower boiling
of nomenclature, ethers are rega rded as points Lhan isomeric alcohols due to their
hydrocarbon derivatives in whlch a hydrogen inability to form hydrogen bonds and get
a tom is replaced by an -OR or - OAr associated.
group, where R and Ar represent alkyl and But lower ethers have slightly higher
aryl groups, resp ectively. n,e larger R group boiling points than 11-alkanes of
is chosen as the parent hydrocarbon. comparable molecular masses due to
dipole-dipole interactions.
Structure : In ethers, the four electron
0 pairs, i.e., the two bond pairs and two lone Higher ethers (containing carbon
atom more than four) have slightly
pairs of electrons on 0-atom are arranged
 lower boiling points than 11-alkanes of Friedel-Crafts reaction:
comparable molecular masses due Lo OCH3
weak van der Waals' forces of attraction.
Polarity: Ethers are polar in nature.
Density : Ethers have low density. All 6 +CHp
Anhyd. AICl3
csl >

¢"'
ethers are lighter than water.
Chemical properties :
Cleavage of C- O bond in ethers :
ROR + HX----+ RX+ ROH 2-Methoxytoluene
CH3
ROH + HX----+ R-X + HzO (Mmor)
4-Melhoxi1oluene
OR OH

6 +HX-► 6
(Major)

ROR' + HX----+ RX+ R'OH

+RX
6
OCH3
+ CH3COCI Anhyd. AICl3
E1hanoyl
ll1e order of reactivity of hydrogen halides is chloride

¢"'
as follows : Hl > HBr > HCI. OCH,

t
CH3 CH3 a COCH3
I I +
CH3- T-0CH3 + Hl ~ CH3-T

rn
-~lclhoxyacctophcnonc
CH3 C (Minor) COCH3
4-Me1hoxy,ce1oph,no11e
(Major)
Electrophilic substitution : Nitration :
- Halogenation : OCH3 OCH3 OCH3
All 3 ~~r
6 v 0
y
6 + H2so4 ) ~ N02 +
0Cl13 llrz in

Amsole
Elhmoic acid y V
Br o- Bromoanisole
•~03
2•Nilro,uusole
(Minor)
N0
2
(Minor) 4•Nitroanisolc
p•Bromoanisole
(Major) (MaJor)

Drag from top and touch the back button to exit

full screen.

88 <<
 15. The C-0 bond is much shorter in phenol 3 1. Ofthe two hydroxy organic compounds ROH
lhan in ethanol. Give reason. (Delhi 20J2C) and R'OH, the first one is basic and other is
acidic in behaviour. How is R different from
11.4 Alcohols and Phenols R'? (Delhi 2013C)
AfJ.ft (1 mark) 32. How would you obtain ethane-1, 2-diol from
ethanol? (Al 2013C)
16. Carry out the following conversion:
Phenol to salicylaldebyde (115, 2020) 33. How would you obtain acelophenone from
phenol? (A l 2013C)
17. Carry out the following conversion ;
Propene to propanol ( 1/ 5, 2020) 34 . Ortho-rutrophcnol has lower boiling point
18. Predict the reagent for carrying out the than p-nitrophenol Why? (Delhi 2012C)
following conversion : 35. Give a chemical test to distinguish between
Phenol to benzoquinone (115, 2020) benzoic acid and phenol. (Delhi 2012C)
19. Predict the reagent for carrying out the 36. Illustrate the followiJ1g name reaction
following conversion : Reimer-Tiemann Reaction. (Delhi 2012C)
Phenol to 2,4,6 -tribromophenol (115, 2020) 37. Give a chemical test to distinguish between
20. Write the preparation of phenol from 2-propanol and 2-methyl-2-propanol.
cumene. ( 1/3, 2020) (Del/ri 2012C)
21. How can you convert the following:
38. Ortho-nitrophenol is more acidic than ortho-
Phenol to chlorobenzene. (113, 2020)
methoxyphenol. Why? (112, De/1,i 2012C)
22. How can you convert the following:
Sodfom phenoxide to o-hydroxybenzoic 39. Give the structure and l UPAC name of the
acid. (1/ 3, 2020) product formed when propanone is reacted
23. How can you convert the following? with methylmagnesium bromide followed by
Elhanol to propanenilrile (1/3, 2020) hydrolysis. (Al 2012C)
P' 24. Write the equation involved in the following 40. Explain the following giving one example :
reaction: Kolbe's reaction Reimer-Tiemann reaction. (1/3, Delhi 2011)
(112, Al 2019, Delhi 2014C, 2013C) 41. How would you convert ethanol to ethene?
25. Give reason for the following : (Al 2011)
Phenol is more acidic than ethanol.
(l/3, Al 2017C, 2015) (2 marks)
26. Write the equalion involved in the acetylation 42. Out oft-butyl alcohol and n-butanol, which
of salicylic acid. (Del/ti 2015) one will undergo acid catalysed dehydration
27. Which of the following isomers is more faster and why? (2/5, 2020)
volatile: 43. Give the mechanism for the formation of
o-n ilrophenol or p-nitrophenol? ethanol from ethene. (215, 2020)
(Delhi 2014)
44. Write the major product(s) of lhe follmving
28. Write the equation involved in the following
reactions:
reaction:
Reimer -Tiemann reaction.
(112, Al 2014, 2013)
29. How is toluene obtained from phenol?
(113, Delhi 2013C)
30. Give a chemical test lo distinguish between
2-peotanol and 3-pcnlanol. Cu
573 K )
(213, 2020)
(112, Del/ri 2013C)
4 5.
Wri te the ~tru ctur cs of the mai n pro
duc ts in
the following rea ctio ns: 52. ~Vr
ite the final product(s) in eac h of
0 the
lollowing reactions :

(i)
0 CH 2 - C - OCH3
11
0
-
1'1lBH•
>
(i) cu,.c11 -C H- CH (.;ul57H.
2 I
011
,

(ii) C H _ OH hl CHc t,.,. "'I· KaOH

~ 5
(ii) W )
(Delli, 2016)
53. I low are the
following conversions carried out?
(i) Pro pen e to propane-2-ol
(213, 2018)
46. Exp lain the (U) Benzyl chlo ride to Benzyl alco
mec han ism of deh ydr atio n steps hol
of eth ano l.
(2/3, De/hi 20JSC)
11• 54. Write the mec han bm of acid
CH ,CH 20H l-13 K > CH2=C H2+H 20 dehydration of
ethanol to yield ethene. (Al 20/SC)
(2/3, 2018C, De/111 20l 5C)
47 . Wn te the 55. Write the mechanism of
pro duc t(s) in the following the following
rea ctio ns: rea ctio n:
OH Cl13Cll2OH --1.ill.4 CH ,Cl l,B r + H O
2
(Al 201'1, 2/3, Poreig11 2014)
~ ICO OII
(i) V 56. Nam e the reagents used
reactions :
in the following

(i) Rromination of phenol to 2,

(ii) CH -C H= CH -C H -0H •I, 6-
3 2 PCC > ? trib rom oph eno l
(215, De/ Iii 2017) (ii) Butan-2 -one to Butan- 2-o I
48. Giv e sim ple che mic al test
s to dist ing uish (ii,) Friedel- Crafts nlkylalion of anis
bet wee n the foll owi ng pair s of com ole
pou nds : (iv) Oxi dati on of prim ary alco
(i) Eth ano l and phe nol hol to
carboxylic acid (Foreign 2014)
(ii) Pro pan ol and 2-m eth ylpr opa
n-2 -ol. 57. Nam e the different reagents nee
(215, Del/ri 2017) ded to
per form the following reac tion s:
49. (a) Arr ang e the following com
pou nds (i) Phe nol to Benzene
in the inc reasing ord er of the ir
acid (ii) Deh ydr atio n of pro pan -2-o l to
stre ngt h: propene
(Ui) Friedel- Cra fts aU.-ylation of ams
p-c reso l, p-n itro phe nol , phe nol o\e
(b) Wr ite the mec han ism (usi ng (iv) Dehydrogenation of etha nol to
cur ved cthanal
arro w not atio n) of the followi (Foreign 2014)
ng 58. I low are the following convers
rea ctio n: ions carr ied
CH2:=CH2 11 out?
o >CH3-C ~+ Hi 0 (i) Pro pcn e to Pro pan -2-o l
(Al 2017)
(ii) Ethyl chloride to Etb ana l (Del/Ji
so. Wr ite the stru ctu re of the pro duc
ts whe n
2014C)
But an -2-o l rea cts with the foll owi ng: 59. Exp lain the following with an example for
(a) CrOJ (b) S0C l2 (Al 2017) eac.h:
(i) Kolbe's reaction,
51. Wr ite the ma in pro duc t(s) in eac h of the
(ii) Rei mer -Tie man n reac tion
following rea ctio ns :
(I) 8 2H11
(213, Al 2014C)
)
(i) Cl-1 1-C H= CI 12 (II) Jll2 0iO U- 60. How will you con ver t :
(i) Pro pen e to pro pan -2-ol,
(ii) Cc,H:; - OH (iil aq.
(i) NaOH ) (D II . 201 6) (ii) Phe nol to 2,4,6-tr init rophen ol?
co 1, 11 e 11
(Dc ll,i 2013)
 61. How will you convert the followi11g: 71. Account for the following :
(i) Propan-2-ol to propanone (i) The boiling point of ethanol is higher
(ii) Phenol to 2,4,6-tribromophenol. than that of methanol.
(Delhi 2013) (ii) Phenol is a stronger acid than an
62. Explain the mechanism of the following alcohol. (Delhi 2011 C)
reaction: 7 2. Write Reimer- Tiemann reaction giving an
11+ example. (Al 20JJC)
CH3-CH2-0H - ;_'-K---4 CII2=CH2 + H20
44 3
(Al 2013) Mf!I■ (3 marks)
63. Explain the mechanism of acid catalysed 73. Write the product(s) of the following
hydration of an alkene to form corresponding
reactions:

6
alcohol. (Al 2012) OH
64. Explain the following behaviours:
(i) Alcohols are more soluble in waler (i) PCC )
tlian the hydrocarbons of comparable
molecular masses. OH

cr
(ii) Ortho-nib·ophenol is more acidic than
ortllo-mcthoxyphenol. (AI 2012) COOH (CJ l,CO),O ➔
65. Give a separate chemical test lo distinguish (ii) I CH,COO H -
between the following pairs of compounds :
(i) Ethanol and Phenol
°
(ii) 2-Pentanol and 3-Pentanol
(Dellti 2012C)
66. I low would you obtain the following :
(i) 2-methylpcntan-2-ol from 2-methyl-1-
(iii}
6 + CH3MgBr
11 ,0 )

74. (a) Show how will you synthesise the

following alcohol prepared by the
. (2020)

pentene reaction of a suitable Grignard reagent

(ii) Acetophenone from ph enol. on methanaJ?
(2/3, Al 20J2C) CH3 -yH- CH2 -0H
67. How would you obtain CH 3
(i) Picric acid (2, 4, 6-trinitrophenol) from (b) Write the mechanism of the following
phenol. reaction:
(ii) 2-Methylpropene from 2-methylpropanol? Ir'
(Delhi 2011) CH =CH2 + H 2 0 ~ CH3 CH 2 0H
2
(AI 2019)
68. How would you obtain the following :
(i) Benzoquinone from phenol 75. How do you convert the following?
(ii) 2-Methylpropan-2-ol from methyl (i) Phenol to anisole
magnesiwn bromide? (Al 2011) (ii) Propan-2-ol Lo 2-mettbylpropan-2-ol
(iii) Aniline to phenol (Delhi 2015)
69. Give the names of the reagents of bringing
about the following lransforrnalions: 76. Predict lhe products oflhe following reactions:
(i) Hexan- J -ol to hexanal .) CH3 -CJ-I-C'-l (I) Bil 16 > ,.
(ii) But-2-ene LO ethanol (Delhi 2011C) (.I - r 2 (ii) 3H 20i/OI 1-

Br,(aq) ,
70. Account for the following : (ii) C6 HsOH - >r
(i) Propanol has higher boiling point than Cu/573 K . )
butane. ( iii) CH JCH 2OH >? (Foreign 2015
(ii) Ort/,o-nitrophenol is more acidic than 77. How are the following conversions carried
or/710-methoxyphenol.
(2/3, Delhi 2011C)
out?
 (i) Benzyl chloride to bcnzyl alcohol (i) Reimer-Tiemann reaction
( ii) Elhyl magnesium chloride to propan-1- (li) Fried al-Cr afts alkylation of phenol
ol (c) Give simple chemical test to distingujsh
(iii) Propene to propan 2-ol. between ethanol and phenol.
(Al 20,s c. 2014C) (De/111 2019)

78. (a) Write the mechanism o( the following 85. (a) Write lhe formula of reagents used in
reaction: the following reaLtions :
llBr
CH,C I 128r + 1110 (i) Bromination of phenol to
CJ1 1CII20 11 -..;.;.;..~
2,4,6- tribromophenol
(b) Write the equation involved in tion of propenc and then
(ti) Hydrobora
Reuner-Tiemann reaction. (Delhi 2014)
oxidation to propanol.
79 (a) Give chemical tests to distinguish between (b) Arrange the following compounJ
the full owing pairs of compounds: groupi. in the increai.mg order of their
(i) Pentan 2-ol and Penlan-3-ol property indicated:
(ii) Methanol and Phenol (1) p-nitropbenol, ethanol, phenol (acidic
(b) o-Nitrophenol is more acidic than character)
o-methoxypbenoL Explain why. (ii) propanol, propane, propanal (boiling
(Al 2013C) point)
80. Draw the structure and name of the product (c) Write the mechanii,m (using curved
formed if the following alcohols arc oxidized. arrow notation) of the following
As.sume that an exce.., of oxidising agent is• · reacllon:
(i) CH,CH ,CH 2CH 20H
( ii) 2-butenol
(iii) 2-methyl-l-propanol (Delhi
SJ. (a) Describe the mechanism of hyd
of ethene to yield ethanol.
(b) Write Kolbe's reaction with an example. 11 .6 Ethers
(Al 201 IC)
82. Acid catalysed dehydration of tert-butanol is fif i (1 mark)
faster than that of II butanol. Explain. 86. Asser tion (A) : (CH ,).iC -0 - CHJ gives
(A l 2011C) (CHJ), C - 1and CH,01-f on treatment with
IQ II (i_marks) _ HI.
Reaso n (R) : 1he reaction occurs by S~l
83. (a) I low do you con\'ert the following:
(i) Phenol to Anisole
mechanism.
(ii) Ethanol to Propan-2-ol (a) Both Assertion (A) and Reaso n (R)
are correct statements, and Reason
(b) Write mechanism of the following
(R) is the correct explanation of the
reaction:
Assertion (A).
C H OH H2S0 1 CH2 = CH2 + HzO
HJK (b) Both AsserLion (A) and Reason (R) are
2 S
(,c) Why phenol undergoes electrophilic correct i,tatements, but Reason (R)
substitution more easil}' than benzene? is not the correct explaJ1ation of the
(Delhi 2019) Assertion (A).
{c) Assertion (A) is correct, but Reason (R)
84. (a) Account for the following:
(i) o-nitrophenol is more steam volatile is incorrect statement.
than p nitrophenol. (d) Assertion (A) is incorrect, but Reason
(R) is correct statement. (2020)
{ii)/ butyl chloride on healing with
sodjum methoxide givei, 2-mcth)•l- 87. Carry out the follow
ing con\'ersion :
propcnc instead of t-butylmethylcther. t-Butyl chloride to t-bulyl cthrl ether
(b) Write the reaction invol
ved 1n the (1/3, 2()20)
following:
88. Predict the reagent for carrying out the 94. How is the following conversion carried out?
following conversions : Anisole to p-bromoanisole (113, Del/Ji 2015C)
Anisole to p-bromoanisole (113, 2020) 95. Write the equation involved in the following
89. Write the equation for the preparation of reaction:
2-methyl-2-methoxypropane by Williamson Williamson synthesis
synthesis. (113, 2020) (112, Al 2014, 2013, Delhi 2014C
J/ 3, Al 2014C, De/1, i 2012C)
90. 'Nrite the equations involved in the following
96. Account for the following :
reaction:
Preparation of ethers by acid dehydration
Friedel-Crafts alkylation of anisole.
of secondary or tertiary alcohols is not a
(112, Al 2019, 1/3, Delhi 2011)
suitable method. (1/3, Delhi 201 JC)
9 1. Write the structure of the main products in 97. Account for the following:
the following reaction: The boiling points of etheri. are lower than
OC 2 H5 isomeric alcohols. (1/3, AI 2011 C)

6 +HJ - ~
(113, 2018)
s;:&,2ma_r_~~)_____
98. Write the mechanism of the following
reaction :
92. Write Lhe product in the following reaction : H' CH CH 0CHiCH1
2CH 3CH20H tTI'P 3 2
CH3
I . HT + H20
CH 3-CH-O- CH 2- CH 3 ~ ? +? (213, 2020, 2/3, Al 2017, Delhi 20 I 6,
(115, Delhi 2017) 2015, 2013, 2013C)
93. Write the main product(s) in the following 99. Give reasons for the followi ng :
reaction : (i) Boiling point of ethanol is higher in
CH 3 comparison to melhoxymethane.
I
C H3-C-O-CH3+ HI~ (ii) (CH3h C-O-CH 3 on reaction with HJ
I gives CJ-·h Oll and (CH3h C-I as the
CH3
main products a11d not (CH 3h C-OH
(J/3, Delhi 2016, 1/2, Al 20 16) and Cll.11. (213, Al 2015)

)
CH 3 0 H
CH 1
31 I I
l. CH1- C - Cli-CH3 b I
. I 2 4. CH 3-0-C- CH3
Cll 2 -CI 11 I
.j 5 CH3
3,3 - Dim~th)'lp<!nl,tn•2-ol 2-Metho:cy-2-methylpropanO!
2. •I 3 2 I
5. 2-Phcnyleth anol
. t
H, C-C=C-CH2 -OH
H3
I
Br
6. 2,5-Dinilrophenol
2-Bromo-3-methrlbut-2-en-1-ol 7. 2-Methylprop-2-en- l -ol
3 2 I 8. 3-Mcthylbut-2-en-1-ol
Q CH=Cl1-Cl12-0H
3. I 9. Butan-2-ol
3-Phenylprop-2-en-l-ol 10. Propane-1,2,3- Lriol