Very I

following questions are ofl mark.

Each of the compound:
0. 1. Writethe lUIPAC name of the following
H;CC=C-CH,-OH

CH, Br
Ans. 2-Bromo-3-nmethylbut-2-en-1-ol
0.2. Write the lUPAC name ofthe following compound:
CH=CH-CH,-0H

Ans. 3-phenylprop-2-en-1-ol
0.3. Write the IUPAC name of the following compound:
CH;-0CH,-CH-CH,
OH
Ans. -methoxypropan-2-ol
Q.4. How would vou convert
ethanol to ethene?
Ans. CH.CH,OH conc.H) S04
Ethánol 443 K CH, = CH, + H,O
Ethene
Q.5. How will you synthesisethe
following alcohol from appropriate alkene:
OH

"OH
Ans. CH,CCHCH, H,0, H
|
CH, CH,-C--CH,CH,
 o-Nitrophenol haslower boiling point than p-nitrophenol. ExpBain.
intramolecular H-bonding o-nitrophenol exists as a discrete molecule whereas due to intermolecular
to
Due
i
p-nitrophenolexists as associated molecules. As aresult of this p-nitrophenol has higher boiling
Ans. H-bonding
pointthano-nitrophenol.
R'OH, the first one is basic and the other is acidic
Ofthe(wo
hydroxy organic compounds ROH and
07 behaviour. Howis
R different from R?
in
alkylgroup
whereas R is an aryl group.
an
following compounds in theincreasing order of their acid strengths:
Ris
Ans.
Arrangethe 6-trinitrophenol [CBSE (F) 2013]
0.8. 4-nitrophenol, phenol, 2, 4,
Phenol < 4-nitrophenol
< 2,4,6-trinitrophenol
bicarbonate solution. Why? [HOTS]
acid but does not react with sodium
Ans.
Phenol is an not liberate CO, from sodium
Phenol is a weaker
acid than carbonic acid (H,CO,) and hence does
Ans.
bicarbonate. [NCERT Exemplar]
conversion of ethanol to ethanoic acid.
a10 Suggest a reagent for
(ii) KMnO4/OH",
(i) CrO,- H,SO4
Ans.
(iv) Acidified KMnO, or K,Cr,0,[CBSE Delhi 2013C]
(ü) H,0*
phenol?
0.11. How is toluene obtained from CH,
OH
+CH,CVAnhyd. AICl;
Ans. Zn (dust)
Toluene
Phenol
following conversion:
l2 Suggest a reagent for the
OH [NCERT Exemplar]

chlorochromate) [NCERT Exemplar]

Ab. CrO,, Pyridine and HCI (Pyridinium This is called
13. What is denatured alcohol? and pyridine in it.
drinking by mixing some copper sulphate
Ans. Alcohol jis made unfit for
ethyl aleohol. [HOTS]
denatured alcohol. drying diethyl ether but not metal.
for
14. metal can be used reacts with
sodium
Ans,
Explain why Sodiumn
atom, ethyl alcohol
Due to presence of an active hydrogen 2CH,-CH,-ONa + H, with
does not react
OH + 2Na hydrogen atomtherefore
2CH, CH2 does not have
replaceable
hand.,
Diethyl ether, on the other by metallic
sodium.
lertiary alcohols?
sodium metal hence can be dried secondary and
0.15. of priuary, alcohols
What is the order of dehydration Primary
[CBSE (F) 2014]
Ans. alcohols >
16. TerNametiarythealcohols>
reagents
Secondary
used in the following reactions:
anisole
of
Friedel-Crafts alkylation(anhyd. AICI,)
Ans. Anhydrous aluminium chloride
Short Answer Questions-I
Each of the questions are of2
marks. [CBSE Delhi 2013]
1,
Howfollowing
wil you convert:
Propene to Propan-1-ol? KOH(ay)
CH.CH,CH, OH
Prupan l ol
-2-01? ,CH, CH, Br
 o-Nitrophenolhas lower boiling point
intramolecularH-bonding than
0.6.
Ans. Due
to
p-nitrophenol o-nitrophenolp-exists
nitrophenol
exists as as a . Explain.
associated molecules. Asdiscrete
a result mol ecule
H-bonding
of this whereas
pointthan0-nitrophenol. due to intermolecular
hydroxy Sp-nitrophenol has higher boiling
Ofthetwo organic compounds
0.7. in behaviour. How is R different from R'?ROH and R'OH, the
first one is c and the basic is other acidic
Ans. Ris,an alkyl group whereas R is an aryl group.

Arrangethe following compounds in the

Q.8. 4-nitrophenol, phenol,,2, 4, increasing order of their acid strengths:
<4-nitrophenol < 6-trinitrophenol [CBSE (F) 2013]
Ans.
Q.9.
Phenol
2,4,6-trinitrophenol
Phenolisan acid but does not react with
sodium
a weaker acid than bicarbonate solution.
Ans. Phenol is
bicarbonate.
carbonic acid (H,CO) and hence does notWhy?liberate CO [HOTS]
from sodium
0.10. Suggest a reagentfor conversion of ethanol to ethanoic acid.

Áns. () CrO,- H,SO4 [NCERT Exemplar]

(i) KMnOJOH",
(iü) H,0*
(iv) Acidified KMnO, or
Q. 11. Howis toluenee obtained from phenol? K,Cr,0,
OH [CBSE Delhi 2013C]
CH,
Ans. Zn (dust) +CH;CVAnhyd. AlCl,
Phenol
Toluene
0.12. Suggest a reagent for the following conversion:
OH

[NCERT Exemplar]
Ans. CrO, Pyridine and HCI (Pyridinium chlorochromate)
Q.13. What is denatured alcohol? [NCERT Exemplar]
As, Alcohol is made unfit for drinking by mixing some copper sulphate and pyridine in it. This is called
denatured alcohol.
21H. Explain why sodiummetal can be used for drying diethyl ether but not ethyl alcohol. [HOTS]
ue 0 presence of an active hydrogen atom, ethyl alcohol reacts with sodium metal.
2CH,-CH,-OH + 2Na 2CH,-CH,-ONa + H,
replaceable hydrogen atom therefore does not react with
Diethyl ether, on the other hand, does not havesodium.
0.15. sodium
What is metal hence can be dried by metallic
the order of dehydration of prirmary, secondary and tertiary alcohols?
Ans. Tertiary alcohols > Secondary alcohols >Primary alcohols
0. 16. reactions: [CBSE (F) 2014]
Name the reagents used in the following
alkylation of anisole
Friedel-Crafts
Ans, Anhydrous ? chloride (anhyd. AlCI)
aluminium
Short Answer Questions-
Each of the following questions are of 2marks.
0.1. How you convert:
() wiPropene
l Propan-1-o1? [CBSE Delhi 2013]
Ethanal to Propan-2-o1? KOH (aq) CH,CH,CH,OH
CH,CH,CH,Br
Ans. = CH, + HBr
Peroxide Propan- I -ol

CH,CH
Propene Alcohols, Phenols and Ethers317
 CH OMgl
(i)
CH CLMpl H',H,0 CH; OH
CH3 H
Jthanal
or cresol? Explain. Propan-2-o1CH,
Q. 2. Which is a stronger acidphenol
All the cresols are weaker acids than phcnols. Methyl group has + cffect
predominates(positive inductive
Ans.
hyperconjugation effect
as hyperconjugation effect but the
on the O H bond and hence all over the +i
these effects inerease the
phenols.
clectron density the cresols are efweaker
fect. Siacinceds, ttrha
As hypereonjugation cffect can operate only through ortho and paru
positions, thereforc, meta-cresol is stronger acid than ortho and positions and not
+l effect at ortho position than at para position(+I effect decreases para-cresols.
with distance),However, due
acid than para cresol. Thus, the order of acidic strength in increasing orderi
d
ortho-cresol to throughsTmggTRSA
ortho-cresol <para-cresol <meta-cresol < phenol \isa wekg,
Q.3. Arrange: water, ethanol and phenol in increasing order of acidity and give reason for
your answer.
Ans. Increasing order of acidity is cth¡nol < water <phenol. The
of a proton is stabilised by resonance whereas the ethoxide jon phenoxide ion obtained after [NCERT Exemplar
destabilised by +l effect of C,H, group. Therefore, phenol is obtained after the removal ofthea rerngva
hand, ethanol is weaker acid than water
because electron stronger acid than ethanol. On proton is
electron density on oxygen and hence the polarity of group in ethanol the ohe
releasing-C,H,
decreasing acidic strength. Hence, acidic strength
Q. 4. Answer the following
O-H bond in ethanol
increases in the order givendecreases
above
which results intethe increases
questions.
(i) Among HI, HBr, HCI, HI is
most reactive towards alcohols. Why?
(i) Of the two alcohols; (a)
Ans. () HI has the lowest
CH,CH-CH,OH
react more easily with conc. HCI in
the
and (6)
presence of ZnC,? CH=CH-CH-CH,OH, which one wil
bond dissociation energy due to [CBSE (F) 2012)
(ii) CH,CH CH,OH longer bond length that is why it is
most reactive
Q.5. Account for the
(i) Phenoldoesfollowing:
not
(ü) Phenol is more react with NaHCO, whereas carboxylic acids
Ans.
easily nitrated than
benzene. react.
(i) RCOOH + [HOTS)
NaHCO, RCOONa + H,CO,
Weaker acid
than RCOOH
QH
ONa
Phenol NalHCO, + H,CO,

Sodium Stronger acid

Such acid base Phenoxide ion than Phenol
(ii)
words, phenol isseaction takes place only if the
not astrong formed is weaker than the reacting acid.In
oher
Nitration acid
enough acid to react with
of-OH involves
group altack
Compared to benzene.
of
electron densityelectonrophile nitronium NaHCO3 +Reftet
Due tonitrated2
ion (NO,) on benzene ring. easily
Q.6. Answer the following benzene
increases. Therefore, phenol is more
()) Dipole
moment questions:
of
(ii) In
Kolbe's reaction,phenol is smaller that of
instead of phenol, methanol. Why? Why?

312 Xam idea

phenoxide ion is
treated with carbon dioxide.
LNCERTExemplat
 phenol,C Obond is less polar due to
Ans.
()Inmethano, C-o bond is more polar due to eleleectctrron-rel
on-wietasihdrawi
n g ng effect of benzene ring
effect of CH, whereas in
(i) Phenoxide ion is more reactive than phenol towards group.
undergoesselectrophilic carbon dioxide which is a aromatic
Substitution with electrophilic
substitution and hence
mechanism of the following reaction: weak electrophile.
Writethe
Q7. conc. H2SO4
2CH,CH,OH 413 K

CH,-CH,[CBSE
-0-CH,Delhi-CH
2016, 2019
The
formation of ether is a nucleophilic bimolecular reaction (SN2) involving(56/4/3),
protonated alcohol as shown below:
2020 (56/3/2)] [HOTSJ
the attack of
Ans.
on
alcohol molecule
H

() CH CH, OH + H+ CH CH, 0H
Ethanol

H H
H
() CH CH : +CH; ÇH O-H CH; -CH Þ CH CH, +H,0

(üi) CH CH0 CH, CH, CH CH, 0 CH, CH, + H

Diethyl ether
0.8. What happens when
i) Phenol reacts with Conc. HNO,?
(ti) Ethyl chloride reacts with Na0C,H,?
Write the chemical equations involved in the above reactions. [CBSE 2019 (56/4/3)]

OH OH
O,N NO2
conc. HNO,
Ans.

Phenol NO,
2, 4,6-Trinitrophenol
CH, CH,-0CH,-CH, + NaCl
) CH, CH,-CI + CH CH,ONa Diethyl ether
Sodium ethoxide
Ethyl chloride
0.9. How would you
obtain
(i) pieric acid (2, 4, 6-trinitrophenol) from phenol? [CBSE Delhi 201!)

") 2-Methylpropene from 2-Methylpropanol? OH

OH OH -NO,
HNO, (conc.) O,N
SO,H
Ans. (i) H,S0,(conc.)
NO,
Picric acid
Phenol SO,H
Phenol-2,4
disulphonic acid CH,
CH, +KOH(alc.) CH,-C=CH,
CH3 CH-CH,CI 2-methylpropene
+sOCl2 CH3C
() CH, CH CH,OH
2-methylpropanol
Alcohols, Phenolsand Ethers313
Short Answer Questions-lI
Each of the following questions are of 3 marks.
Q. 1. Explain the mechanisnn of the following reactions:
() Addition of Grignard's reagent to the carbonyl group of a compound
followed by hydrolysis.
(i) Acid catalysed dehydration of an alcohol forming an alkene.
forming an addng
OR
Give the nmechanisnm for the fornmation of ethene from ethanol.
(ii) Acid catalysed hydration of an alkene forming an alcohol. [CBSE 2020 (56/12,1
Ans. (1) Step I: Nucleophilic addition of Grignard reagent to carbonyl group. (HOTS)
J+

LoRMg-X -OMg-x
Adduct
Step II: Hydrolysis
H,O
-OMg-X OH + Mg(OH)X
R R
(ii) Refer to NCERT Exercises, O. 19.

(üi) + H,0

Alkene

Mechanism:
Step I: Protonation of alkene to form carbocation by
electrophilic attack of H,0".
HÞ + H+ H,0*
H
+ HÞ -H H,0
Step II: Nucleophilic attack of water on carbocation.
H
H
+
H,ö Þ-H
Step IIl: Deprotonation to form an alcohol

H,Í'
Q. 2. How do you convert the following:
(i) Phenol to anisole
Deli2015/
ii) Propan-2-ol to 2-methylpropan-2-ol [CBSEL
(üii) Aniline to phenol
OH ONa OCH,
+ NaOH +CH,Br
Ans. (i)
Phenol Anisole

emistry-XIl
 OH OH
PCC
(i) CH;-CH-CH, - CH,-C-CH, () CH;MgBr
Propan-2 -ol (ii) H,0 CH-C-CH,
CH
4
2-methylpropan-2-ol

NH) N,CI OH
NaNO,/HCI H,O
(iü) 273-278 K Warm
Aniline Phenol

Arrangethe following compounds in decreasing order of acidity. [NCERT Exemplarl

CH
0. 3.
() H,0, ROH, HC=
(Gi) CH,0KO OH, o,NO-OH, CH,OH
(ii) CH,OH, H,0, C,H,OHCH
HC=
Ans. (i) H,O> ROH >
(i) 0,N -OH > CGH,OH > CH,0 -OH

(ii) CH,OH > H,0 > CH,0H

04 Give one chemical test to distinguish between the following: [CBSE 2019 (56/5/1)]
(i) Phenol and propan-1-ol
(ii) Ethanol and dimethyl ether
(i) propan-1-ol and 2-Methyl-propan-2-ol
Ans. () Phenol gives a violet coloration with neutral FeCl, solution while propan-1-ol does not.
6C6H,0H + FeCls ’ [Fe (0C6H;)6]* + 3H* + 3HCI
Phenol

(i) Ethanol gives yellow precipitate of iodoform when warmed with NaOl (NaOH\,) while dimethylether
does not.
CH,CH,OH + 41, + 6NaOH CHI, ! + HCOONa + 5Nal + SH,O
Ethanol Lodoform
(yellow ppt)
(i) Propan-1-ol being a 1° alcohol does not produce turbidity at room temperature on treatment with
Lucas reagent (anhyd. ZnCl, + conc. HCI) whereas 2-methylpropan-2-ol being a 3° alcohol gives
turbidity immediately at room temperature on treatment with Lucas reagent.
CH3 CH;
Anhyd. ZnCl,+ conc. HCI
CH3-C CH, CH-C-CH,

OH CI
2-Chloro-2-methylpropane
2-methylpropan-2-ol (Turbidity appears inmediately)

ganiccompound A' having molecular formula C,H, on treatment with aqueous H,SO, gives
Which on treatment with HCVZnC, gives C'. The compound C on treatment with ethanolic
KOH gives back the compound 4'. ldentify the compounds A, B, C. [HOTS]
CI

ADs, A= C= CH-CHCH,
CH,CH= CH2
Propene
B= CH-CH CH,
2-chloropropane
OH
Propan2 -ol

Alcohols, Phenols and Ethers3IS

 aq. H, SO4 HCVZnCl,,
CH--CH =CH, CH3-CH-CH,
(Hydration)
Propene
A OH
Propan -2 - ol
B Ethanolic KOH
CH,-CH-CH, CH4CH
Propene =CH,
CI
2-Chloropropane
C

oxidation, it gives a compound B but on we

Q. 6. A compound 4' is optically active. On mild with Dis also formed from B by reaction
oxidation gives another compound 'C'.Calong with iodine
D.
and alkali.Deduce the structures ofA, B, C, (HOTS)
OH

CH CH,-H CH
CH CH, CCH,
Ans. Mild oxidation B
A Ethyl methyl ketone
sec-Butyl alcohol
Vigorous I,/NaOH
Oxidation

CH; CH, COOH CH CH, COOH + CHI;

Propanoic acid D
C
Iodoform
Propanoic acid

Q.7. Account for the following:

(1) Rectified spirit cannot be converted into absolute alcohol by simple distillation.
(ii) Diethyl ether does not react with sodium.
(iii) Phenols do not undergo substitution of the -OH group like alcohols.
Ans. () Rectified spirit containing 95% ethyl alcohol and 5% water forms an azeotropic mixture which distils
at a constant temperature of 351.13 K.
(i) Since diethyl ether does not contain an active hydrogen attached to oxygen like alcohols and phenols.
itdoes not react with sodium.
(üi) The CObond in phenols has some double bond character due to resonance and hence cannot be
casily cleaved by nucleophile. In contrast, the CO bond in alcohols is apure single bond and hence
can be casly cleaved by nucleophile.
Q.8. Write the main product(s) in each of the following reactions: [CBSEDelhi2016]
CH,
(i) CHJ-Ç 0-CH + HI
CH,
(ii) CH,-CH=CH, (i) B,H,
(ü) 3H,O,/OH
() ag. Na(OH
(i) CçHOH
(i) CO2, H*
CH,
CH,
|
Ans. (i) CH3C-0CH, + H
CH3-C + CH3 OH
Methyl
CH3
Methyl CH3 alcohol
Tert. butyl iodide
tert. butyl ether
() BzH6
(ii) CH;-CH-CH, (i) 3H,O,/OH CH3CH, CH,-OH
Propene n- propyl alcohol
 OH

()agNaOH
COOH
OH
(i)CO,/H*
Salicylic acid

following conversions?
Phenol

bringthe
willyou benzylalcohol
HowPhenolto
(i)Phenol m-bromophenol
(i) [HOTS]
aspirin,
Phenolto
i) ÇH, ÇH-Cl ÇH-OH
OH Ch, hv
CH,CVAICl3. NaOH (aq)
Zn dust
A
Toluene Benzyl chloride Benzyl alcohol
Benzene
Phenol
NO, NO,
OH Br,/FeBr3
HNO, (conc.)
Zn (dust) -Br
H,SO, (conc.)
(i) Benzene Nitro
Sn/HCI (conc.)
benzene
Phenol

NH,
OH
N,CI NaNO,/HCI
H,0 273-278 K -Br
-Br

m-Bromophenol

CH,
OH CH, OCOCH3
ONa -coOH
OH -COOH
(i) CO, 410 KJ4-7atm
NaOH H,SO4 Aspirin
(üi) (ii) H,O/H+ (conc.)
Phenol
[CBSE 2020 (56/I2))
following?
10. How would you obtain the
() Benzoquinone from phenol bromide (F) 2011]
2-Methylpropan-2-ol from methylmagnesium [CBSE (AI) 2011,
W)
(üi) Propan-2-ol from propene
QH
Ans. NazCr0,/H,S04

Phenol
Benzoquinone OH

OMgBr H,O CH hCH;

CH3 CH3 CH
(i) CH3 CH, + H,mMgBr H3
2-methylpropan-2-ol
broneSium
Propanone Methyl
CH CH3
H+
CH;
(ül) CH3 -CH =CH; + H,0 Markovnikov's
addition OH
Propene Propan-2-ol

nsandEthers31
Q. 11. Give reasons for the following:
) Phenol is more acidic than methanol.
(ii) The C-0--H bond angle in alcohols is slightly less than the tetrahedral angle
(ii) (CH,)}C-0-CH, on reaction with HI gives (CH,),C-I and CH,-OH as the
(109° 28),
[CBSE Allahabad main
2015] pr(HoOTS
ducts
and not (CH)}C-0H and CH,-I.
Ans. () In phenol,the phenoxide ion obtained afterthe removal of aproton is stabilised by
resonance
there is no resonance in the alkoxide ion of methanol.
Moreover, due to +/ effect of CH, groupthe electron density in Q--H bond increases whereas
release of H difficult.
(i) It is due to the repulsion between the lone pair of electrons on oxygen atoms,
which makes
H
(iii) The reaction between (CH),COCH, and HI follows Syl mechanism. For
formation of product is controlled by stability of the carbocation formed in thean Syl reaction, the
slowest step. Since
tert.butyl carbonium ion (CH),C) foimed after the cleavage of C-0 bond in the slowest sten is m
stable than methyl carbonium ion (CH) therefore
Q. 12. Give the major products that are
(CH,)}C-I) and CH,OH are the main produete
formed by heating each of the following ethers with HI.
CH,
() CH,-CH,-CH-CH,-0-CH,-CH;
CH3
(ü) CH;-CH,-CH,-0-C-CHCH,
CH,
(iiü)
Ans. [HOTS)
(i) CH,CH, CH CH,OH + CH,CH,I
CH3
CH3
(i) CH,CH,CH,OH + CH,CH,-C-I
CH3
(üi) CH + -OH
Q. 13. The following is not an
appropriate reaction for the preparation of tert.-butyl ethyl
C,H,ONa + (CH),C-CI ether:
(i) What would be the (CH),C 0C,H;
major product of the given
(ii) Write a suitable reaction?
reagents used.
reaction for the preparation of
tert-butyl ethyl ether, specifying the names of
Justify your answer in both cases.
Ans. (i) The major product of the CBSE Sample Paper 2016) [HOTSI
given reaction is
(CH,-CH,O Na) is astrong nucleophile as2-methylprop-1-ene,
It is because sodium eu
well as a strong base, Thus, elimination reaction
predominates over substitution reaction,
CH,
CH, ¢-CH, + CH,CH,ONa CH, C=CH, + NaCI + CH,CH,0h
Sodium ethoxide
C
Isobutylene
tert-butyl chloride (2-methylprop-1-ene)
Xam idea Chemistry-XII
 (i)Topreparetertiary butyl ethyl ether, the alkyl halide should be primary, i.e., ethyl chloride and the
nucleophile should be
tertiary, i.e., tertiary
butoxide ion. It is because the
mechanismand primary alkyl halides are most reaction occurs by SE2
reactive in SN2 reactions.
CH,
CH,
+ CH,CH,CI
Ethyl chloride CH COC,H, + NaCI
CH,
Sodium-tert-butoxide CH¡
tert-Butyl ethyl ether
Answerthe
following questions:
24 are etthersinsoluble in water?
() Why equation:
Completethe reaction
OH

(i) How will you know whether a given OH group is alcoholic or phenolic in nature?
in water because due to the
Ethers are insoluble bigger size of the alkyl groups, the
4ns. ethersfails to form intermolecular H-bonds with water. oxygen atom in
H,0/H* OH
(i)
4-Methylhept-3-ene 4-Methylheptan-4-ol
A2 Phenolic OH group gives blue or violet colouration with neutral FeCl,, while alcoholic OH
group
does not.
t A
compound A' having molecular formula C,H0 is found to be soluble in concentrated sulphuric
ocid. Itdoes not react with sodium metal or potassium permanganate. On heating with excess of HI,
it gives a single alkyl halide. Deduce the structure of compound A and explain all the reactions.
[HOTS]
Ans.
() As compound Adoes not react with sodium metal or potassium permanganate, it cannot be an alcohol.
(i) As compound Adissolves in conc. H,SO4, it may be an ether.
(i) As compound Aon heating with excess of HI gives asingle alkyl halide, therefore, compound Amust
be a symmetrical ether.
(") The only symmetrical ether having molecular formula C,H0 is diethyl ether. Thus compound '4
is diethyl ether, CH, CH, 0-CHCH,.
+

conc. H2 SO4 CH,-CH,-0 CH,-CH,

CH,CH,0-CH,CH, A H
HSO,
Diethyl ether Soluble oxonium salt
HI

CH,CDiethyl
H,0CH, A
ether
CH, 2CH,CH,I
Ethyl iodide

16, Write
the structures of the main products in the following reactions:

NaBll,

(i) CH=CH, + H,0

(iü)
0C,Hs [CBSE 2018)
+ HI

Ethers
Alcohols, Phenols and
 OH
-0CH,
Ans. (i)
NaBH4 OCH,
Methyl (2-oxocyclohexyl)
cthanoate
Methyl (2-hydroxycyclohexyl)
ethanoate
CH=CH,
(ii) + H,0
H*
CH-CH,
OH
Ethenyl benzene
1-Phenylethanol
OH

(ii) + HI
+ CH_-I
Ethoxy benzene Phenol Iodoethane
Q. 17. Write the products of the following reactions:
OH

() CH, CH,-0-CH,+HI (ii) + Br2 CS,

QCH,
(iii) + CH,COCI anhyd. AICI,
Ans. (1) CH3-CH,0CH,
Ethyl methyl ether
+ HI CH3-I + CH,--CH, -OH
Methyl iodide Ethyl
alcohol
OH
OH OH
(ii) + Br, CS Br
273 K
Phenol
2-Bromophenol
(Minor) Br
4-Bromophenol
(Major)
QCH,
OCH, OCH,
(iil) + CH CI Anhyd. AICI,
CH,
Phenol
2-Methoxy acetophenone -CH:
(Minor)
4-MethoXy acetophenone
Q. 18. What happens when (Major)

(i) (CH,),C OH is
(iü) Anisole is treated with Cu at 573 K,
treated with
(iiü) Phenol is treated with Zn dust?
Write chemical
CH,CVanhydrous AICl3, [CBSE
IF20

CH,
equations in support of your answer.
Ans. CH,
(i) H,C-C-CH, Cu

573 K H,CC=CH, + H,0

OH Isobutylene
tert- butyl alcohol

Xamidea Chemistry-Xl
 Q-CH, OCH3 Q-CH,
+CH,-CI
Anhyd. AICI,
CH, +
(i) 2-methoxy
Anisole
toluene (Minor) CH,
OH 4-nethoxy toluene (Major)
+Zn + ZnO
Benzene
Phenol

happenswhen
What acid is treated with (CH,CO),0/H"?
0.19.
) Salicylic
() Phenolis
oxidised with Na,Cr,0,/H?
is treated with CH,C/anhydrous AICI,?
(ii) Anisole
answer.
Write chemical equation in support of your [CBSE 2019 (56/3/1)]

COOH COOH
() OH CH,-C H
-OC CH; + CH, C-OH
Ans. +
CH,
Aspirin
Salicylic
acid Acetic anhydride
OH

(i) Na,Cr,07
H,SO4
Phenol

Benzoquinone
OCH; OCH,
OCH3
CH,
+ CH,CI +
(iii) Anhyd. AlCl/CS,
Anisole 2-methoxy toluene CH,
(Minor) 4-methoxy toluene
(Major)
 Long Answer Questions
narks.
Rach of the following questions are of 5
Q. 1. )Write the formula of reagents used in the following reactions:
(a) Bronnination of phenol to 2, 4, 6-tribromophenol
(b) Hydroboration of propene and then oxidation to propanol.
ii) Arrange the following compound groups in the increasing order of their property indicated:
(a) p-nitrophenol, ethanol, phenol (acidic character)
(6) Propanol, propane, propanal (boiling point)
(iti) Write the mechanism (using curved arrow notation) of the following reaction:
CH,-CH,-OH, CH; CH;OH
CH3-CH;-0-CH,-CH, + H,0 [CBSE Delhi 2017]
(CBSER Ans. () (a) Br,(aq)
H
(b) B,HÙ, H,0, H,0, and OH
(ii) (a) Ethanol < Phenol <p-nitrophenol (b) Propane < Propanal < Propanol
H H H

(üi) CH, CH, 0: +CH CH t -H CH, CH, Þ* CH,CH, +H,Þ

Alcohols, Phenols and Ethers/321

 (Ö) How can you obtain phenol from(a) Cumene,(b) Benzene sulphonic acid, (c) Benzene
chloride? diazonium
(ii) Write the strueture of the major product obtained from dinitration of 3-methylphenol.
(üii) Write the rcaction invelved in Kolbe's reaction. [CBSE 2019 (56/2/1)
CH, CH
CH;-CH CH;-C-0-0-H OH

+O,
Ans. () (a) + CH3CO CH,
H,0
Cumenc Cumenc Phenol Acetone
hydroperoxide
+
SO,H so,Ga ONa OH

NaOH +NaOH H
(b) fuse, 573 K

Benzene Phenol
sulphonic acid

N,CI OH

warm
(c) + H,0 + N, + HCI
Benzene Phenol
diazonium chloride

OH OH
O,N
HNO,(Conc.)/H,SO4(conc.)
(ii) Dinitration
CH, CH3
3-Methylphenol NO,
2,4-Dinitro-5-methylphenol
(iii)) Kolbe's reaction:
+
OH ONa OH OH
+NaOH CO, -COONa H -cOOH
400 K, 4-7 atm

Phenol Sodium Salicylic

phenoxide acid
'C. Both
Q.3. An aromatic compound'4' on treatment with CHCI/KOH gives two compounds B' and
Band Cgive the same product D' when distilled with zinc dust. Oxidation of D gives Ehe
which may
alsobe
molecular formula CH,0, The sodium salt of Eon heating with sodalime gives F [HOTS]
obtained by distilling A with zine dust. Identify A to F.
OH OH OH

Ans. A= B= -CHO
C=

Phenol o-Hydroxy benzaldehyde

CHO
pHydroxy benzaldehyde
CHO ÇOOH

D= E= F=
Benzoic acid Benzene
Benzaldehyde

322/ Xam idea Chemistry-XIl

 Reactions
involveri.
OH OH
CHC; /KOH OH
-CHO
A B
Phenol oHydroxy benzaldehyde CHO
Zn (dust)
C
distillation
p-Hydroxy benzaldehyde
Zn (dust)
ÇOOH distillation
(i) NaOH CHO
(ii) NaOH/CaO (0)
630 K
Benzenc
Benzoic acid D

() Give equations of the following reactions: Benzaldehyde

(a) Phenol is treated with conc. HNO,.
(b) Propene is treated with B,H, followed by
(c) Sodium -butoxide is
i) How will you distinguish
treated with CH,CI. H,0,/0H.
beetween butan-1-ol and
(ii) Arrange the following in
Phenol, ethanol, water increasing order of acidity:butan-2-ol?
OH
OH [CBSE 2019 (56/2/1)]
O,N
Ans. ()) (a)
Conc. HNO3
NO2
Phenol

NO2
2, 4, 6-Trinitrophenol
(b) CH;-CH CH, () B,H,
Propene (i) H,0,/OH CH,CH,CH,
Propanol
OH
CH,
CH3
|
(c)
CH3-C-0-Na + CH Ci CH3 -C-OCH, + NaCl
CH3 CH,
Sodium tert.butoxide
Methyl tert. butyl ether
(u) Butan-2-ol when warmed with IL in NaOH (NaOI)
butan-1-ol does not respond to this test. gives yellow precipitate of iodoform while
CH,-CH,-CHCH, +4L, +6NaOH CHI, | +CH,CH,COONa + 5Nal + SH,O
Lodoform
OH (yellow ppt)
Butan -2 -ol
(ii)
Q.5. () Ethanol < water < phenol
What happens when
) phenol reacts with
(b) ethanol reacts with bromine water?
(e) anisole CH,COCpyridine?
reacts with HI?
Write the between:equations
(ü) Distinguishchemical involved in the above reactions.
(a) Eihanol
(b) and phenol
Propan-2-ol
and 2-methylpropan-2-ol |CBSE (F) 2016]

Alcohols, Phenols and Ethers

 OH OH
Br Br
Ans. () (a) + 3Br,(aq) + 3HBr

Phenol
Br
2,4,6-Tribromophenol

Pyridinc
(6) CH CH,--OH + CH,C- CI
Ethanol Ethanoyl chloride CH,-C-0-CH-CH,
Ethylethanoate t HCI
OCH; OH

+ HI + CH
Anisole Methyl iodide
Phenol

ii) (a) Phenol gives violet colourationwith FeCl, solution but ethanol does not
6C,H,OH + FeCl, [Fe (0C;H,) + 3H* + 3HCI
Phenol Violet colouration
complex
(b) Propan-2-ol when warmed with I, in NaOH gives yellow precipitate of
2-methylpropan-2-ol does not respond to this test. iodoform whle
CH,-CH-CH, t 41, + 6NaOH CHI, ! +
Lodoformn CH3-CO0 Na + SNal + SHO
OH (yellow ppt.)
Propan-2-ol
Q. 6. (i) Write equations of the following reactions:
(a) Bromine in CS, with phenol
(b) Treating phenol with chlorofornm in the
presence of ag. NaOH
(c) Anisole reacts with HI
(ii)) Distinguish between
(a) Ethanol and Diethyl ether (b) Propanol and t-butyl alcohol
OH [CBSE South 2016
OH OH
Br, in CS, Br
Ans. (i) (a) 273 K
Phenol
Br o-Bromophenol
p-Bromophenol (Minor)
(Major)
+
OH +
ONa ONa OH
CHCl; + ag. NaOH CHCI, CHO
+NaOH CHO
Phenol
Sulicylaldehyde
OCH, OH
(c) + HI
CH,I
Anisole
Phenol Methyl ivdide whilediethylehe
(ii) (a) Ethanol when warmed with ,
in NaOH gives yellow precipitate of iodotorm
does not.
CH, CH, OH +41, + 6NaOH SNal t SH,0
CHI, ! + HCOONa +
lodotomn
(yellow ppt.)

Xam idea Chemistry-XIl

.or-butyl alcohol on treatment with the Lucas reagent immediately gives turbidity while propanol
does not produce turbidity at room temperature.

CH3 CH;
Anhyd. ZnCl, + HCI (conc.)
CH,-C-CH,
Lucas reagent CH,-C CH,
OH
rert-butyl alcohol C1
tert- butyl chloride
(Turbidity appears immediately)