name of the following

IUPAC
8. Write
compound. Foreign2014

PREVIOUS YEARS H O - C H - C H - C H - O H

EXAMINATION QUESTIONS OH
hydroxy organic
compounds
TOPIC1 9. Of the
two
the first one is basic and
ROH and R OH, behaviour. How is R
in
1 Mark Questions other is acidic
different from R? Delhi 2013C
1.Write the IUPAC name of the following: toluene obtained
from phenol?
10. How is
CHa Delhi 2013C
has lower boiling point than
CH--ÇH-CH, 11. 0-nitrophenol
p-nitrophenol. Explain. Delhi 2013
CH, OH obtain ethane-1, 2diol
CBSE 2018 Examination pagper 12. How would you
2. Write the IUPAC from ethanol? AllIndia2013C
name of the following
compound. structure of hex-1-en-3-ol
13. Draw the
compound. Delhi2012
H,C-C C-CHOH 14. Draw the structural
formula of
2-methylpropan-2-ol molecule. Delhi2012
CH Br
AllIndia 2017 15. Write the IUPAC name of the following
3. Write IUPAC of the
name given compound.Foreign 2012
compound:
CH2-CHz-OH CH-CH=CH-CH-CH-CH
OH
AllIndia 2016 16. The C-0 bond is much shorter in phenol
4. Write the IUPAC name of the given than in ethanol. Give reason Delhi2012
compound.
17. How could you convert ethanol to ethene?
0,N OH
AllIndia 2011
NO2 Delhi 2015 18. Write the equations involved in the
5. Write the IUPAC of following reaction.
name the given
compound: Reimer-Tiemann reaction AllIndia2012
HO-CHCH =(-CH Or Write Reimer Tiemann reaction giving an
example. Alindia 2011
CH Forelgn2015 19. Draw the structure of
2,6-dimethylphenol.
6. Which of the following isomers is more AllIndia2011
volatile: o-nitrophenol or p-nitrophenol? 20. Write the chemical equation for the
AllIndia 2014 preparation of phenol from benzene using
7. Name the alcohol that is used to make the oleum and sodium
hydroxide. Delhi 2011
following ester 21. Write the structure of the
molecule of
compound whose IUPAC name is
1-phenylpropan-2-ol. All India 2010
CH-C0-CH CH 22. Write the mechanism
of acid
of ethanol to dehydration
CH3 AllIndia2014C
yield
ethene. All India 2015C
CHAPTER10:AAlcohols, Phenols and Ethers 247

Or Explain the mechanism of dehydration (ii) Ortho-nitrophenol is more acidic than

steps of ethanol.
ortho-methoxy phenol. AllIindia 2012
CHCHOH CH=CH, + H,O 31. How would you obtain Delhi 2011
() picrie acid from phenol?
Delhi2015C,AllIndia 2013 (1i) 2-methyl propanol from 2-methyl
propene?
2 Marks Questions 32. Account for the following.
23. ) Arrange the following compounds in (i) Propanol has higher boiling point
the increasing order of their acidic than butane.
acidic than
strength. ii) Ortho-nitrophenol is more

p-cresol, pnitrophenol, phenol ortho-methoxy phenol. Delhi 201C

i) Write the mechanism (using curved 33. Account for the following.
decrease
arrow notation) of the following (1) The boiling points of alcohols
reaction. with increase in branching of the alkyl1
H,0* chain.
CH=CH CH-CH, +H,0 1i) Phenol does not give protonation
AllIndia 2017 reaction readily. Delhi 20110
24. How are the following conversions
34. How are the following conversions carried
carried out?
out
i) Propene to propan-2-o1?
() benzyl chloride to benzyl alcohol?
(i) Ethyl chloride to ethanal? Delhi2014c (i) methyl magnesium bromide to
25. Write the mechanism of the following 2-methylpropan-2-ol? Delhi2010
reaction. 35. How are the following conversions carried out
CH,CHOH HBr CH,CH,Br + H,O
(i) Propene to propan-2-o1?
Foreign2014 Delhi2014 ii) Ethyl magnesium chloride to
26. How will you convert the following. propan-1-ol? Delhi 2010
i) Propan-2- ol to propanone? 36. Write the mechanism of hydration of
i) Phenol to 2,4,6-tribromophenol? ethene to ethanol. Forelign2010
Delhi 2013 37. Give one chemical test to distinguish
27. How will you convert between the following pairs of compounds.
) propene to propan-1-o1? (i) Phenol and benzoic acid.
Gi) ethanal to propan-2-ol? Delhi 2013 (i) 1-propanol and 2-propanol, Delhi2010c
28. How will you convert
() propene to propan-2-ol? 3 Marks Questions
(1i) phenol to 2,4,6- trinitrophenol?
38. (a) How will you synthesis the following
Delhi 2013 alcohol from appropriate alkene
29. Explain the mechanism of acid catalysed
hydration of an alkene to form
corresponding alcohol. All India 2012
30. Explain the following behaviours. OH
soluble in water b) Write the mechanism of the following
i) Alcohols are more
reaction All India 2019
than the hvdrocarbons of
comparable molec ular masses.
CHCHOH-CH= CH +HO443 K
 CHEMISTRY
248 CBSE
Solved
Papers:Ch
CHEMISTRY

Chapterwise

sions carried out.

39. (a) conversion

Show how 45.

( i )

How are
the
P r o p e n e >
following
P r o p a n - 2 - o 1 ?

you will
following alcohol
suitable Grignard rby the
the
ction of a
Ethyl
magnesium
chloride

reagent on methan (ii)

Benzyl alcoho?
P r o p a n - 1 - o l ?

CH-CHCH-OH ii)
Benzyl
AllIndia2014C
chloride
»

namne the product

Write the CH ism of the following
structure
and
(b) 16. Draw the alcohols are

reaction Allmechanis
4 6 following
formed if
the excess of
that an
Indla 2019 oxidised.
Assume

used.
agent
is

40. (a)
CH=CH,+H.0CH,CHOH oxidising
) C H , C H C H , C H , O H

Butan-1-ol has a higher boiling point (i) 2-butanol

than diethyl ether. Delhi2012
(6) Write the Why? (iii)
2 - m e t h y l - 1 - p r o p a n o l

mechanism of the following obtain the following,

would you
reaction: 47. How from phenol?
Benzoquinone
i) from methyl
2CH,CH,OH 2-methyl propan-2-01
(ii) m agnesium bromide?
413 K
from propene?
CH,CH-0-CH,-CH, All India 2019 (ii) Propan-2-ol
All India 2019 Allindio2011; Foreign2011
41. ) for the following:
Complete the following reaction and 48. Account
ethanol is higher
suggest a suitable mechanism for the
(i) The boiling point of
reaction: than that of
methano.

CH,CH.OH 443K Phenol is a stronger acid than an

(i)
alcohol.
(i) Why ortho-nitrophenol is steam point
volatile while para-nitrophenol is (ii) Propanol has higher boiling
than butane. Delhi2011c
less volatile? 2018 C
49. i) Describe the mechanism of hydration
42. Predict the products of the following of ethene to yield ethanol.
reactions. Write Kolbe's reaction with an
ii)
() CH,CH =CH, B _ 2 example. AllIndio 2011C
i) 3H20/ 0OH 50. (i) Describe the mechanism of acid
1i) CH,OH a catalysed dehydration of ethanol to
Cu573 K yield ethene.
ii) CH,CH,OH Foreign 2015 (ii) Describe the chemical test to
43. How are the following conversions carried distinguish between ethanol and
out phenol. All India 2010C
i) Benzyl chloride to benzyl alcohol?
ii) Ethyl magnesium chloride to 5 Marks Questions
propan-1-ol?
51. (a) How do you convert the
(i) Propene to propan-2-o1? AllIindio2015 following
() Write the mechanism of the following
() Phenol to anisole
44.
reaction. (i) Ethanol to propan-2-ol
b) Write mechanism of the following
CH,CHOH- CH,CH,Br+H,O reaction
(i) Write the equation involved in
Reimer-Tiemann reaction. AllIndia2014
CH,OH HS0, CH=CH, +HO 443K
CHAPTER 10: Alcohals, Phenols and Ethers 249

(c)Why phenol undergoes electrophilic

substitution more easily than benzene? H-bonding
Delhi 2019 Ho+
52. (a) Account for the following:
) 0-nitrophenol is moresteam
volatile than p-nitrophenol.
o-nitrophenol
(i) t+butyl chloride on (Intramolecular
heating with
sodium methoxide gives H-bonding)
2-methylpropene instead of H-bonding
t-butylmethylether. ---HO 0-
b) Write the reaction involved in the
following: p-nitrophenol
(Intemolecular
G) Reimer-Tiemann reaction H-bonding)
(i) Friedel-Crafts alkylation of (1)
(c) Give simple chemical test to
phenol
OH
distinguish between ethanol and 7. CH-CH-CH,
phenol. Delhi 2019 Propan-2-ol (1
8. Propane -1, 2, 3-triol.
Explanations 9. +-effect of alkyl group increases the basic
1. IUPAC name of given structure character of alcohols and --effect of alkyl group
increases the acidic character of alcohols.
CH, OH
CH h-cH, In R-OH, R possesses only +1-effect, i.e. only
alkyl groups which increases electron density on
CH-CH 0-atom of 0-H bond and hence, it shows basic
character while, in R'OH, R' possesses --effect in
is 3, 3-dimethylpentan-2-ol its alkyl chain which decreases electron density in
28,-CH,-O the 0-H bond.

CH, Br
OH CH
2-bromo-3-methylbut-2-en-1-ol
3. IUPAC name of the given compound is
(1
1O O-n
Phenol Toluene (1
2-phenylethanol. (10
11. In o-nitrophenol, intramolecular H-bonding
4
NO2 OH occurs which makes it more volatile whereas, in
p-nitrophenol intermolecular hydrogen bonding
NO, exists which makes it less volatile. That's why,
0-nitrophenol has lower boiling point than
IUPAC name 2,5- dinitrophenol (1) p-nitrophenol (
12. CHCH,OHconc.Hso,
443 K
5. HO-CH-H=¢-H,
CH=CH CH-CH, ÇH-CH,
CH
IUPAC Name 3-methylbut-2-en-1-o (1) C CI OH OH
6 0-nitrophenol is more volatile due to chelation (1)
(weak intramolecular H-bonding). While, 13. CH-(H,-H-¢H--H=CH,
p-nitrophenol is less volatile due to strong
intermolecular H-bonding which causes the OH
association of molecules.
Hex-l-en-3-ol
(1)
250 Solved Papers CHEMISTRY
Chapterwise CBSE
OH
sOgH
14. CH-CH, 20.
NaOH
CH -HO
Oleum (H,S,0)
>methylpropan-2-ol (1 353 K Benzene sulphonic
15. CH- H= H-¢H-H,-CH, Benzene
acid

OH ONa OH
sO,N
Hex-4- en-3-ol (1)
HH0
16. Inphenol, C-O bond acquires partial double NaOH, 575K
bond character due to resonance while, in -Na SO3
-H,O
alcohol, C-O bond has single bond character. (1) Sodium benzene
Sodium phenoxide
Phenol
sulphonate
17. CH CH OH conc. HSO4 CH,=CH, + HO
443 K
Ethanol Ethene
(Dehydration) (1) 21.
- H,-ÇH-CH,
18. Reimer -Tiemann Reaction The reaction of
phenol with chloroform in the presence of sodium OH
hydroxide, a-CHO group is introduced at o-position 1-phenylpropan-2-ol
of benzene ring. This reaction is known as
22. Steps invoved in acid catalysed delhydration of
Reimer-Tiemann reaction. The intermediate alcohol are
substituted benzal chloride is hydrolysed in the
presence of alkali to produce salicylaldehyde. () Protonation of alcohol
i) Formation of carbocation
OH (i) Elimination of proton

(aq) NaOH, 340 K

CH-CH-OH CH,= CH,+ Ho
+CHCl-NaCl,-H,O 4431

Phenol Mechanism This reaction involves the following

steps:
QNa+ QNat Step I Formation of protonated alcohol
CHC2 2NaOH CH(OH)2
Fast
-2NaCI
CH-CH-0-H+H CHCH-0
Intermediate Protonated ethanol
benzene chloride (ethyl oxonium ion)

(1/2)
QNa QH Step I1 Formation of carbocation
CHO CHO
Di HCI Slow
-H,O -NaC CH-CHo Protonated ethano H Rate detemining
step
2-bydroxybenzaldehyde
(Sallcylaldehyde) (1)
NOTE Asmallamount of phydroxybenzaldehyde Is also CH-CH2+H,0
Carbocation
formed. Step Il1 Loss of proton to give alkene
19. QH
H3C CH HCHCH, -H
CH= CH,Ethene (1/2)
23. (i) Electron withdrawing groups such as-NO9
increases the acidic character
while, electron
releasing group such as-CH, decreases
2, 6-dimethylphenol acidic character thus, the
the increasing order ol
acidic strength is
eHAPTER 10: AICohols, Phenols and Ethers
251

OH OH OH

CH NO2
(p-cresol) (Phenol) (p-nitrophenol)

) The mechanism ior the formation of carbocation is as follows:

H
CH-CH +H-H CHy-CH+ H,0
to propan-2-ol
24. (i) Propene OH

CH-CH= CH,- H0/H CH,-CH-CH3

(1
Propene [Markownikoff's
addition ofl H 20]
Propan-2-ol

(ü) Ethyl chloride to ethanal

CH-CH,-Cl
NaOH
CH,-CH TO
OH CrO3/PCC CH,-CHO
Ethanal
Ethyl chloride SN2 Ethanol (1
reaction [Oxidation]

25. CHCHOH on reaction with HBr follows Sn 2mechanism.

HBr H + Br
S 2 mechanism

Step 1 CH-CH,-OH+H* CH,-CH-0H2

CH3
(2)
Step 2 BrCH,CH,oH, Br.CH.OH2
L Intermediate
-OH
CH,CH,Br +H0
HC-CHCH
CrO HC-C-CH,
PC
26. (i) Propan-2-ol to propanone Oxidation

OH
Propan- 2ol Propanone

(ii) Phenol to 24,6-trlbromophenol OH OH

Br Br
3Br In H,0
OJ- (Bromination)
Phenol
Br
2,4,6-tribromophenol 1)

27. (i) Propene to propan-1-ol aq. KOH 33

CH CH=CH, HBr +
CH,CH,CH,Br
Propyl bromide H,-H2-H,-OH
-KBr
Propan-1-ol
Propene

(1)
converting propene Lo propan01 1S nydroboration-oxidation reactin
NOTE Alternative method for
 CHEMISTRY
252 Chapterwise CBSE
Solved
Papers:

CH-CH2)2BH
CH-CH CH;, (CH
CH-CH=CH2+ (H--BH2) > CH-CH
Propene Diborane
HBH2
3ÖH3 C H C H 2 - C H O H + B { O H ) 3

CH-CH=CH,
(CH-CH-CH2),B H20/H202
Propan-f- o

(ii) Ethanal to propan-2-o OH

CH
HC
- 8+
CH OMg H
CH,Mg
C=0 H
H CH Propan-2-o
Ethanal Markownikolrs rule while
Adduct with
accordance
of H.so, takes place in
Opene to propan-2-ol Addition
converting propene to propan-2-ol.
CH-CH-CH
CHCH=CH, + H,0
Propenc
OH
Propan- 2 ol

of conc. HSO4
and cOnc. HNO, yields
of phenol in the presence
to 2,4,6-trinitrophenol Nitration
(1) Phenol
2,4,6-trinitrophenol (picric acid). OH
OH NO2
O,N
+3HNO H,504
(Conc.)
(Conc.)
Phenol
NO2
2,4,6-trinitrophenol
(Picric acid)

29. The steps involved in this process are

water on carbocation
0) Protonation of alkene () Nucleophilic attack of
alcohol
(i) Deprotonation to form an

Following steps areinvolved in the acid catalysed hydration of an alkene.

I Protonation of alkene to give carbocation by electrophilic
attack of H,0 as shown below:
Step
HO+ H H,0 (1/2)
H

Step II Nucleophilic attack of water on carbocation formed.

H O-H

- + H,

Protonated alcohol

Step Ill Deprotonation to give an alcohol.

H

H :OH

+H0 +H,O
Protonated alcohol
(1/21
 253
CHAPTER
10:Alcohols Phenols and Ethers

aConsider polar nature of water as well as alcohol, presence of H-bonding.

30.
i) Acidity isthetendency to give a proton. It depends upon the stability of phenoxide ion formed (in caseo
Higher the stability of phenoxide ion, more will be the acidic characte.

(i) Due to the presencCe ol polar -OH bond, alcohol molecules can form H-bonds with the water m01ccueoa
the water-aiconol interaction becomes stronger than the water-water or alcohol-alcohol interacuod
That's why, alcohols are more soluble in water. H-bond
- 8+ 0+ 0
H-0...H-Q.....H-0. H-Q H
R H H
R
Intermolecular H-bonding between alcohol and water
Hydrocarbons, on the other hand, have no polar bond and hence, the water-hydrocarbon interaction remains
weaker as compared to water-water or hydrocarbon- hydrocarbon interactions, i.e. hydrocarbons ao no 0
(1)
H-bond with water. Thus, they remain insoluble in water.
and hence, tne
in the 0-H bond decreases
() Due to strong-R and -1-effect of the NO, group, electron density
loss of a proton becomes easy.

0 H 0-H
NO2

-I-effect -eflect
a positive charge on the
decreases the electron
phenolic O-atom, makes
density in the 0-H bond,
the release of prolon easy
makes release of proton easy

Further, the o-nitrophenoxide ion left after the

loss of a proton is stabilised by resonance. Thereby making
C-nitrophenol a stronger acid.
-N=0 0

0
-N*

" =o
density in the O-H bond increases thereby
In contrast, due to +R-effect of-OCH, group, the electron

making the loss of a proton difficult.

O- H O-H
CHY

destablised by resonance because

ion lelt after the loss ol a proton is
Furthermore, the o-methoxyphenoxide a weaker acid. Thus,
each other thereby making o-methoxy phenol
the two negative charges repel
acidic than o-methoxypheno.
0-nitrophenol is more

-CH CH
(1)
 254 Chapterwise CBSE
Solved Papers: CHEMIS
Papers:

31. ()
OH
OH
NO, NO
Conc.HNO,
conc.H,S0
Phenol
NO
Picric acid

CH
(i)
3CH,-C=CH2 + BH3- (CH),CHCH,],B 3(CH,),CHCH,OH
>-methyipropene Hydroboration OH-H,B03
or HC-CH- CHOH

CH
2-methyl propanol
S2(1)
Themolecules of propanolare held together by intermolecular hydrogen bonding while the
have
only
weak van der Waals' forces of attraction. molecules of
butare
Hydrogen bonds are much stronger so the boiling point
propanol is much higher than butane. od
(i) Refer solution 30 (i).
to
33. (i) Since, branched chain alcohols
have minimum surface area,
between them, hence
boiling point decreases with increase in therefore, of
minimum force of attraction occu
(i) In phenols, the lone branching alkyl chain.
pairs of electrons on the oxygen atom are
resonance and hence, are not
easily available for protonation. delocalised over the benzene
ring due to
34. (i) CH-C CH-OH
aq.a AOH

Benzyl chloride Benzyl alcohol

- +

(i)
OMgBr QH
CH,MgBr+
Methyl magnesiumCH--CH CH-- CH HO
chloride g(OH)Br CH--CH,
Propanone CH
H,
35. (i) CH,=CH-CH, " " 2 methylpropan-2-ol
Propene CH-CH-CH, (1)
OH
Propan-2-0
6-8
OMgCI
(ii) CHCH,MgCI , CH-CH-CH,
Ethyl magnesium
chloride
CH CH CH,OH
36. Refer to solution 29.
37, i) Phenols do not (1
give brisk effervescence of CO, on reaction
acid gives. with
carbonates and (2)
bicarbonates while carboxylic
Ph-OH+Na£O, No reaction
2CH,COOH +NacO,
2CH,cOÖNa" +HO Co, t +
CHAPTER 10: Alcohols, Phenols and Ethers 255
il Propan-2-ol on reaction with sodium
and (warm) gives a yellow hydroxide Step 1 Protonatlon of ethene to form carbocation
precipitate
iodoform (CHI,) while, propan-1-ol of by electrophilic attack of H,0"
such test. gives no
NaOH H
CH-CHCH, +41,CHI,d+CH coÖÑa + 5Nal
OH
CH,CH,+ L-HCH,-CH, H, +

(Propan- 2 Ol) Step 2 Nucleophilc attack of water on cartbocation

H
+5HOCH-CH; -CHOH+ 41,
(Propan-1-O1)
No reaction
+

CH-CH+ H,=H,C-CH, -0-H

(a) Given. alcohol Step 3 Deprotonatlon to form ethanol
R

sVnthesised from (2-methyl-2-butanol) can be

follows
2-methyl-2-butene (alkene) as H

CH-CH-T+H,3
H
+H20 H,C-CH,OH + H,0*

2-methyl-2-butene
O 40. (a) Butan-1-ol has higher boiling point than diethyl
ether because of the presence of hydrogen
2-methyl-2-butanol (major)
bonding in it.
(b) Mechanism of given reaction follows
(b)CH-CH,-OHH_
443 KCH,=CH, + H,O
Ethanol
S 2mechanism which is shown below:
Mechanism H

Step 1. Addition of H* ion 2CHCHOH 413K

CHCHOCHCH,
Step 1 CH,CH-H +H* CH-CH5-H
CH-CH-0-H/CH
/HCH,-CH,-0-H
H Step 2 CH,CH-öH + CH,CH2-O
Step 11. Formation of carbocation
CH,CH2-0-CHCHy+H20
CH,-CH,0-HCH-CH,+H H
H
Step 3 CH-CH-0-CH,CH -

Step 111. Formation of ethene (alkene)

H

CHCH, CH, = CH, +H* CH,CHOCH CH,+H*

H
41. (i) Refer to solution 22.
(ii) Refer to solution 11.
39. (a) HCH +CH,CHMgBr CH-CHCH2
42. (i)CH,-CH=CH (0)B,H
CH, OMgBr (11) 3H ,00OH
CH
CH-CH,-CHOH (1)
Propanol

Mg(OH)Br + CH-CH-CH,OH

CH
(ii) CgH,OH or
oH Br

reaction is as follows
Br
(b) Mechanism of the given Br
2,4,6 tribromophenol (1)
CH=CH+HOCH,CH OH
(ii) CH,CHOH ACH CHO
Ethanal
(1)
 CHEMI
256 Chapterwise
CBSE
SOlved
Popers:
MIST
ion,
produced by the
by the losso
phenoxide
43. (ii) The
phenol,
is
stabilise lised by resonance
by negative charpe
CHCI CHÖN proton
of the
to
delocalisation

contrast,
alkoxide ion. ho
In
(i) benzene ring. resonance.
On theother
NaOH g)HCI stabilised by
positive ind
is not
it is
further
destabilised by inductive
Benzyl CHOH effect of alkyl
group.
chloride
H OH
Benzyl alcohol
-

(i) Refer to solution 35 (ii). Phenoxide ion

(ii) Refer to solution 35 (i). (1)

structures of phenoxide ion
Resonating
44. i) Refer to solution 25. (1)
ü) Reimer-Tiemann Reaction
Refer to solution 18. (1%)

45. (i) Refer to solution 35 (i).

(i) Refer to solution 35 (i). (1)
C- -0
(ii) Refer to solution 43 (i).
RO + H*
ROH
46. (i) CHCH CH CHOH- Alkoxide ion
Oxidation
(ii) Refer to solution 32 (i).
CH CH CH COOH (
Butanoic acid (1) 49. (i) Refer to solution 29.
sodium phenoxide
reaction When
(ii) CH,-CH-CH,CH Oxidation (ii) Kolbe's with NaOH] is
generated by treating phenol
OH heated with CO, at about 400 K and
under 4 to 7
2-butanol
CH-CCH,CH, atmospheric pressure, sodium salicylate is
formed as major product, which on acidification
gives salicylic acid, e.g.
2-butanone
(1
H OH ONa
(iii) CH,C-CHOH CH,- -COOH
Oxidation (9) NaOH 400
-H,O
CO2 47 atm
CH, CH,
2methyl-1-propanol 2methylpropanolc actd (1) Sodium phenoxide

OH OCoONa OH
coON
47. O NayCr,0
H0 (1) Rearrangement
H,S04
Phenol

OH
Benzoquinone
COOH
(i) Refer to solution 34 (ii). H,O/H
(1)
(ii) Refer to solution 35 (i).
Salicylic acid
alcohol increases with increase
48. (i) Boiling point of (2-bydroxy benzoic acid)
atoms (increase in van
in the number carbon
of
der Waals forces). That's why boiling
point of 50. (i) Refer to solution 22.
methanol. (1) (2)
ethanol is than that of
higher
CHAPTER10: AlCohoIs, Phenols and Ethers
257
i) Ethanol when warmed with NaOH +
I,
yellow ppt. of iodoform while phenol doesgives
not
Step I1I Formation of ethene by the
give this test.
elimination of a proton
CH,CHOH+4NaO1
Ethanol
CHI, H H
H
lodoform
HCOONa" +
(Yellow ppt) H -C+H
H
Nal+ HO+ 2NaOH H Ethene
CHOH+ NaOH No yellow ppt (1) The acid used in step I is released in step II. To
Phenol
drive the equilibrium to the right, ethene is
51. (a) (i) Phenol to anisole removed as it is formed.
OH - t (c) Phenol undergoes electrophilic substitution
ONa more easily than benzene because phenolic ion is
more stable than benzene.
52. (a) (i) Ino-nitrophenol, there exists intramolecular
+NaOH
-H0 H-bonding which makes it more volatile
whereas in p-nitrophenol, intermolecular
Phenol Sodium hydrogen bonding exists, which makes it
phenoxide less volatile.

OCH3 (i) t-butyl chloride on heating with

sodium
methoxide gives 2-methyl propene instead
of t-butyl methyl ether because, in case of 2°
CHCl and 3 alkyl halides due to steric hindrance,
-NaCl elimination competes over substitution.
(b) (i) Reimer-Tiemann reaction On treating
Anisole phenol with CHCl, (chloroform) in the
presence of sodium hydroxide, a -CHO
(ii) Ethanol to propan-2-ol group is introduced at ortho position of
u benzene ring.
CHCHOH CH,-CHOtMgar
Ethanol OH ONa
CH CH
CHCl2
(i) CHCl
CH,--0MgBr* CH-CH-OH NaOH

H
Propan-2 ol OJ (ü) aq. NaOH

Phenol Intermediate
(b) Mechanism ONa OH
Step I Formation of protonated alcohol
CHO CHO
H H HHH H
Fast
H--¢-o-H + H* H-CC-0-H
Salicylaldehyde
H H H
Ethanol Protonated alcohol (i) Frledel-Crafts alkylation of phenol
(Ethyl oxonium lon) Phenols when treated with alkyl halides in
the presence of anhydrous AIC undergo
Step I1 Formation of carbocation alkylation to form alkyl substituted phenols.
It is the slowest step and hence, it is the rate OH OH OH
determining step of the reaction. CH3
Anhyd.
HHH H H +CH-CI AlCly
H - ¢ - ¢ + H20o
0-CTesol
H CH3 (Minor)
HH H
Carbocation
p-cresol
(Major)
 3 Marks Questions
Marks
3
MISCELLANEOUS QUESTIONS 8. What
happens when
(a) phenol reacts with conc. HNO
2 Marks Questions with NaOC
(b) ethyl chloride reacts with Na00
1. Define with Write the chemical equationsinvo
equation:
a) Riemer-Tiemann reaction reactions. All Indla2019Ved
the above
(b) Williamson's main products in each
2.
synthesis All India 2019 9. Write the ofof.the
Write the equations involved in the following reactions:

following reactions: CH3

(a) Kolbe's reaction
(b)
Friedel-Crafts alkylation of anisole All Indla ) CH-C-0-CHg + HI
2019
3. Name the
different needed to
CH3
reagents
perform the following
reactions:
i) CHg-CH=CH,BHg

) Phenol to benzene.
agNaOH
i) Dehydration
of propan-2-ol to propene. Gi) CeHs-OH 0i) CO2,
(ii) CeHsOn
(il) Friedel-Crafts acetylation of anisole. HAll india 2015
iv) Dehydrogenation of ethanol to 10. Write the final products in each of the
ethanal. Foreign 2014 following reactions:
4. Name the
reactions
reagents used in the following CH3
i)Bromination of phenol to CH-C-0-CH3+ HI
2. 4.6-tribromophenol.
i)
CH3
Butan-2-one to butan-2-ol.
ii)
i) CH3-CH-CH--CH, Cu673K
Friedel-Crafts alkylation of anisole.
iv) Oxidation of primary alcohol to OH
carboxylic acid. Foreign 2014 (ii) CsH5-OH 9 CHCytaq.NaOH
5. Name the
reagents used in the
i) H* Delhi 208
reactions
following 11. How do you convert the
) Nitration of phenol following.
to (i) Phenol to anisole?
2,4,6-trinitrophenol
ii) Butanal to butanol.
i) Propan-2-ol to
2-methylpropan-2-0!
(i) Aniline to phenol?
(ii) Friedel-Crafts acetylation of anisole. 12. ) Write the
Delhl 2015
(iv) Oxidation of primary alcohol to mechanism of the follow
reaction.
aldehyde. Foreign 2014
6. Write the equations involved in the
2CH,CH,OH
following reactions (ii) Write CH,CH0-CHCH
i) Reimer-Tiemann reaction. the
equation involved in the
acetylation of salicylic acid. Delhl
(i) Williamson synthesis. 0elhi 2014 13. Give reason 203
for the
7. Write the equations involved in the
( Phenol is more following.
acidic than
following reactions i) The C-0-H methanu
bond
slightly less than angle
) Williamson ether synthesis. is in alcobo
(ii) Kolbe's reaction. Delhi20140c the tetrahedra
angle (109° 28 ).
CHAPTER 10: hols, Phenols and
Ethers 263
Gii) (CHa sC-0-CHg on reaction
HI gives with (17) Preparation of ethers by acid dehydration
(CH,,C-I and
the main products and CH-OH as of secondary or tertiary alcohols is
not not a suitable method.Delhi 2011C
(CHCOH and CH,-L All India 2015 5 Marks
14. Write the major product in the following Questions
19. (i) Write the productss in the following reactions:
equations. All India 2015C
OH
) CH-CH,OH s
C0OH
OH (CH,CO
?
H

i) + CH-CI anhyd. AICc CH3

(b) CH-CH- 0- CH-CH
(i) CHCl+ CH,CH2-ONa? HI?
15. Name the following according to IUPAC (c) CH-CH=CH- CH OH
system. Delhi2015C PCC?
() CH-H-CH-CH (i) Give simple chemical tests to
distinguish between the following
OH pairs of compounds:
Br (a) Ethanol and phenol.
(b) Propanol and
CH3 2-methylpropan-2-ol. Delhi 2017
in
20. () Write the formula of reagents used
the following reactions:
CH (a) Bromination of phenol to
2, 4, 6-tribromophenol.
(ii) CH--CH-C b) Hydroboration of propene and
then oxidation to propanol.
CH (ii) Arrange the following compounds in
16. How are the following conversions carried out. the increasing order of the property
i) Propene to propan-2-01? indicated:
chloride to benzyl alcohol? (a) p-nitrophenol, ethanol, phenol
i) Benzyl
(ii) Anisole to p-bromoanisole? pelhl 20150 (acidic character).
17. Explain the following with an example for (b) Propanol, propane, propanal
each (boiling point).
i) Kolbe's reaction (ii) Write the mechanism (using curved
arrow notation) of the
ii) Reimer-Tiemann reaction following
reaction:
(iii) Williamson ether synthesis
All India 2014C CH-CH-OH CHCHOH
18. Account for the following
(i) The boiling points of
than isomeric alcohols.
ethers are lower

acidic than
CH-CH-0-CH-CH,+HO H
Ortho-nitrophenolis m o r e
(i) Delhl 2017
ortho-methoxy phenol.
 264 Chapterwise
CBSE
SOved Papers rs CHEM

5
of topic 2,.
Explanations
solution
Refer to
(ii)
(iv)
PCC
(Pyridinium lorochromate)
chloro

1. (a)
Riemer-Tiemann Reaction
On
treating phenol with chloroform n
CH-CH2-OH
Ethano PCCCH,-CHO
C
Ethanal
Presence of sodium hydroxide, a-CHO 8roup bromine o r bromine wate
water (Br, ir
ntroduced at ortho position of benzene 4. (i) Aqueous

resulting in salicylaldchyde. This reactio rimg OH OH

known as
Riemer-Tiemann reaction. Br
OH + 3Br,Bromination

ONa +3Br2(in H,0)

CHCl, Phenol
CHCl NaOH Br
aq NaOH 2, 4, 6-tribromopheny
Phenol
ONa Intermediate OH (ii) Sodium borohydride (NaBH,
CHO CHO
NaBH 4
H CH3 -CH2-CH
Butan-2-one

OH
Salicyladehyde
(b) Refer solution
to 6 of Topic 2. CH-CH-CH,--C
2. The equations involved in the following reactions are Butan -2.ol

(a) Kolbe's reaction (ii) CH,Cl in the presence of anhy. AICI , asaCGa
a cala
and CS, as a solvent.
OH
ONa OH
OCH OCH
COOH
NaOH O ) Co
O +CH,Cl
Anhy. AlCl
(Friedel-Crafts
Phenol Salicylic acid Anisole alkylation)
2-methoxy toluene
(Minor)
(b) Friedel-Craft alkylation of anisole OCH
OH OCH OCH3
Anhyd CH,
+ CH,C AlCl
CS

Anisole CH
4-methoxy toluene
(Minor)
(Major)
CH
(Major) (iv) Acidified potassium permanganate or acidile
3. (i) Zn dust and heat
KCrO
OH
R-CH OH* R-COOOH
1 alcohol HS04 (4xh
Zn dust
5. (i) Conc. HNO, and conc.
Phenol
HSO4
Benzene
OH OH
(ii) 85% H,PO, /440K NO
O,N
OH Conc. HN0,t
conc. HS04
CH-CH-CH, H,Po4 Phenol
Propan-2-ol
NO
CH CH= CH, + HO 2,4.6-trinitrophe

Propene (Picric acd

CHAPTER 10: cohols, Phenols
ond
and Ethers
Ethers
(ii) H in presence of Pd
O 265
CH,-C
CH-CH,-C_H H.Pd
Butanal OH
OH

i) Refer
(iv)
to CH-CH-CH-CHOH
solution 5 of
dinium chlorochromate topic 2
Butanol CHCl, +aq.Naon
H
CHO

2-hydroxybenzaldehyde
(Salicylaldehyde)
(CrO,) with(PCC), complex of
chromiumtrrioxide a (1)
11. (i)
OHPhenol to anisole
and [O].
CH CH OH
pyridine and HCl ONat OCH
1 alcohol CH CHO
Acetaldehyde
(i) Refer to solution 18 of Topic1. +2NaOH| CH,Br
6
4*1/2 2) JS2 (-NaB)
) Refer to solution 6 of Phenol
Topic 2. (0) Anisole
(1)
7. (i) Refer to solution 3 of (1) (1 Propan-2-ol to 2-methylpropan-2-ol
Topic 2.
) Refer to solution 49 OH
(ii) of Topic 1, (1)
8. (a) When phenol reacts with conc. (1) H-CH-CH,Cr,0,/H,50, [O] CH CH3
acid is obtained. HNO, then picric Propan-2-o -H,0 Acetone
OH
OH
Conc. HNO, 0,N
OMgBr OH
NO2
[O) Y CH,MgBrCH-CH-CH3 |-MH'H,0CH-C-CH3
g(OH)Br
Phenol
CH3 CH3
NO Adduct
2-methylpropan-2-01

(1
Picric acid
(b) When ethyl chloride reacts with (ii ) Aniline to phenol
diethyl ether is obtained. NaOCH, then NH2 NCr
CH,CH-Cl + Na OC>Hs CHCH,O C,Hs +NaCl NaNO,/HCI

Diethylether
O (273-278 K)
Diazotisation
Aniline Benzene diazonium
chloride
9.
CH CH OH
(i)CH--O-CH, + HICHy-¢-I +CH,OH
Dil. H,S0 OJ+N,f+ HCI
CH3 CHy Hydrolysis
Phenol (1)
(i)BaHo
(i) CH-CH=CH2 (i) 3H,0,/OH3CH, CH, CH,OH of
12. (i) The given reaction depicts the preparation
(Propanol) 1
ether through dehydration of alcohols
OCH OCH, OCH CH-CH,--OHonc.H504
413 K
CoOH Ethanol

aq. NaOH CH-0-CH,+HO

(üi(O Co.H Ethoxy ethane

(2-hydroxy benzoic acid)

Salicylic acid] COOH Mechanism This reaction proceeds through
(4-hydroxy benzoicid) nucleophilic bimolecular substitution reaction,
reaction are as i.e. Sy2 mechanism.
70. Final Product(s) of the given The main steps are as follows:
following: Step I Protonation of alcoho!
(i) Refer to solution 9 (i)
Cu/573K
(i) CH3-CH-CH-CH3
CH3-CH2C-CH3
CH-CH-A-H+H
OH
(1) CH-CH0-H
 Chapterwise CBSE
Solved
CHEMISY
Papers:C
CHEMISTRY
Step II
Nucleophilic attack by protonated
alcohol molecule.

unprotonate cd alcohol molecule o n

H,0
CH,CH-0:+ CH-CH,L9 SN2
> CH,CH,
-0-CH2CH,
+

(Slow) H
Step I H
Loss of
proton to form
ethoxyethane.
H

9-CH2-CH, ast, CH,CH,0-CHCH,+H

Ethoxyethane

OH OCOCH
COOH
(i) COOH
CHCO CHcOÕNa +CHCOOH
Acetic acid
O Few drops of
CH,CO Conc. H2So4
2-acetoxybenzoic
Salicylic acid
acid (Aspirin)

13. (i) Refer to solution 48 (ii) of topic 1.

nols, both the oxygen and the carbon
h ls-orbital
attachedoftoHitand
aresp
sp-hybridised.
-orbital carbon
Two of the alkylsp"-hybridisei
to
Oorbitals of C
and oxygen overlap separately
- 0 , o-bonds respectively, while the remaining two sp°-orbitals contaln lon pairs
to of
greater
form
electrons
lone

angle (109°28) duei

tetrahedral
The C-0-H bond angle is slightly less (108.9°) than the
pair-lone pair repulsion than lone pair-bond pair repulsion. and the alkyl halid alide forme
the alcohol
(ii) In case of unsymmetrical ethers having two different alkyl groups, n a i a e is iormed
from
is tertiary, the alkyl
nature of the alkyl group. If one of the alkyl group
depend on the
the tertiary alkyl group.
CH
CH
CH,-OH +CH, I
CH,-C-OCH,+ HI
SN Methyl alcohol

CH
CH
formation of products is
occurs by Sl
mechanism and the
This is due to the reason that the reaction bond in protonated ether.
carbocation resulting, from
the cleavage of C-O
Controlled by the stability of the of C-0 bond givs
carbocation, therefore, cleavage
is more stable than methyl
Since, a tert-butyl carbocation
then reacts with I ion to form
carbocation. This carbocation
methyl alicohol and the more stable tert-butyl
tert-butyl iodide.

4 (i) CH CHOH CH,CHCI + POCl, + HCl

Chloroethane
OH QH
OH
CH3
Anhyd.AlCly
+ CHCI
(ii)
(Minor)
(0-isomer) CH3
(Major) (p-isomer)

CHOCH, + NaCl
(ii) CH,-Cl + CHCH,ÖNa CH
Methoxy ethane

Br CH
CH,
15. (i) CH,-CH-CHCH,
(ii) (ii) CHc- HCI
CH
OH Butan-2-ol 2-methylbromobenzene 2,2-dimethylchloropropane
CHAPTTER 10: Alcohols, Phenols
ond Ethers
16. (i) Refer to
solution 28( (i) 267
(i) Refer to solutio 34 (i) topic 1
topic 1.
OCH, (1)
OCH
(i)
QCH
Br2 Br
(in ethanoic
acid)
Anisole
o-bromoanisole
(Minor)
Br
p-bromoanisole
17. (i) Refer to solution 49 (i) topic 1.
(Major)
(i) Refer to solution 18 of topic 1.
(1
(il) Refer to solution 3 of topic 2. (1)
(
18. (i) Boiling point is directly proportional to the
Ethers have low intermolecular forces existing in compound.
a
polarity because they do not show any association
On the other hand, their isomeric by intermolecular hydrogen bonang
alcohols have strong H-bonding and so their boiling points are (1
) Refer to the solution 30 (ii) of topic1 nigl
(1
(ii) Secondary and tertiary alcohols on dehydration lead to the formation of alkene and not ethers due to
stability of 2" and 3" carbocation. Hence, not suitable. C (1)

19. (i) (a) OH OCOCH

COOH COOH
(CH,CO),0 +CH,COOH
H+
Acetic acid
Salicylic acid Aspirin
CH CH
(b) CH CH-0-CH-CH, CH-¢-I+CH3-CHOH
ethanol
2-ethoxy propane
2-iodopropane
PCC
(c) CH-CH=CH-CH-OH CH-CH=CH-CHO (2)
But-2-en-l-al
But-2-en-l-ol

(i) (a) Ethanol and phenol with NaOH solution

ethanol and phenol. Ethanol
reacts
not react.
Iodoform test is used to distinguish
does
a yellow precipitate
of iodoform while phenol
containing iodine. On heating, it gives
CHI, J+ R--c-ONa
3NaO1
NaOH+I Nal+NaOI +HO; CHCHOH + lodoform

-OH +Na0 No reaction

test is used to distinguish

2-methylpropan-2-ol

Propanol and 2
alcohol. Victor-Meyer's with
(b) while 2-methylpropan-2-0l Is AgNO, and HNO,.
Propanol is 1° alcohol
given alconO 1S reated Wh Pl, and thenthe colour produced, the
them. In this
both of
test, first the colour witn
different
NadH. By identilying
gives
Thefinal product obtained
alcohols are identified.
268 CBSE
Salved
Papers:
CHEMis
ISTRY
Chapterwise

CH,CH,OH
< CH,CH,CHO<
Primary alcohols give blood red colour CH,CH,CH,
(Propanal) (Propanol)
of boiling point)
(Propanc)

RCH,OH RCH,1 gN,

order

1'alcohol RCH,NO (increasing

given
reaction,
alcohol acts as nucleoph

0=N-OH, R-CNO2 (ii) In

and
attacks o n
carbocation (CH,-CH,
OH
N-OH to form
It is the intermediae
diate
NaOH (CH,CH,0-CH,CH).

Blood r ed
H of ethers
Secondary alcohols give blue colour involved in the preparation
step,
R CH,CH,OH
CHOH CH-ARNo R,CHNO2 CH-CH-ÖH2 /
R R
2alcohol 0=NOH, R,C-NOD2 CH,.CH-0-CH2CH3 + H,0

N= 0
H
NaOH

Blue colour

20. (iMa) Bromine in presence of water can carry out

bromination of phenol to 2, 4, 6-tribromophenol.
OH OH
Objective Questions
3 Br/H20
BI Br (For Complete Chapter)

Phenol
Br
1 Mark Questions
of hydrogen
2, 4,6-tribromophenol
1. Decreasing order of reactivity
(b) Diborane (BH3) reacts with propene to give halide acid in the conversion of
tripropylboranes as addition product which
on

oxidation with alkaline HO, give alcohols.

ROH RX is
(a) HCl> HBr> HI > HF
BH6 (b)HI > HBr > HCl> HF
3CH-CH=CH, H202/OH
(CH,-CH,-CH)-B- (c)HF > HCl> HBr >HI
B(OH), +3CH,-CH CH-OH (d)HF> HBr> HI > HC1
ii)(a) Electron withdrawing group such as-NO, 2. Boiling point of alcohol is comparatively
increases the acidic character while electron
releasing group such as-CH, decreases the
higher than that of corresponding alkane
acidic character. Morcover, the phenoxide ion, due to
produced by the loss of a proton by phenol, is (a) intermolecular hydrogen bonding
stabilised by resonance due to delocalisation of the (b) intramolecular hydrogen bonding
negative charge on the benzene ring. Therefore, (c) volatile nature
the increasing order of acidic character is
(d) None of the above
OH OH
3. The most suitable reagent for the
conversion of
CH,CH,OH<
Ethanol
Phenol RCH,OH RCHOis
NO2 (a) KMnO4 (b) KCrO7
p-nitro phenol
(c) PCC (d) Cr O
4. The correct order of
(b) Alcohols (CH,CH,OH) undergoes strong dehydration ot
hydrogen bonding while hydrocarbon
such as alcohols is
hydrogen bonding.
exhibit (a)1°> 2>3°
propane does
not
(b) 3> 2 >1°
but not
Aldehydes show hydrogen bonding (C) 2°>1°> 3° (d)1°> 3°> 2
stronger than alcohols.
 APTER 10 ohols, Phenols and Ethers 269

Which ofthe
th following compounds is most
5. acidic?
Explanations
(a)CH (b) C.H
(c)CH=CH (d) CHOH 1. HI> HBr > HCl> HF.
reagent reacts fastest with nucleophilicity ofa
6. Lucas This is due to the fact that, the
(b) 2-butanol increase in size. As
halide ion increases with
(a) 1-butanol
thus,
(d) 2-methyl-1-propanol increases from F° toI",
(c)2-methyl-2-propano size of halide ion
followed by
Tion will be a nucleophile
better
7. Which one of the following alcohols, is Br,Cl and F.
used as an antifreeze reagent and for bonding in
making explosives? 2. Because of intermolecular hydrogen
molecules.
associated
(a) Glycerol (b) Glycol they exist as
alcohols, is
a m o u n t of energy

(d) Phenol Consequently, a large therefore,

these bonds and,
(c) Ethanol
required to break than that of
the
order of boiling point for are higher
their boiling points
8, The correct hydrocarbons (hydrogen bonding
and tertiary
primary (1°), secondary (2°) corresponding
hydrocarbons).
(3) alcohols is isabsent in
(b) 3°> 2°> 1° chlorochromate (PCC) prevents
(a)1°>2°>3 3. Pyridinium to carboxylic acid.
1°> 3 (d) 2°> 3°> 1° further oxidation of aldehydes
(c) 2°>
PCC, RCHO + HO
is RCH OH
9. Picric acid CH2Cl2
(a) 2,4,6-tribromophenol
(Solvent) of
b ) 2.4.6-trinitrotoluene
alcohols involves the formation
(c) 2,4.6-trinitrophenol 4. Dehydration of More the stability
of
intermediates.
carbocation
of the above of alcohol
(d) None
carbocation, more will be the ease

does not give

10. Which of the following
towards dehydration.
is
of carbocations
iodoform test? The order of stability
(b) CH,OH
(a) CHOH 3>P>1 of alcohols is
(c) (CH, CHOH (d) All of these The order of ease
of dehydration
of anisole is 3°>2>1°.
11. The chemical
name
(b) methoxy benzene can give proton
(a) ethanoic acid choices, C,H,OH
5. Among given
(d) acetone
(C) propanone
(H ) most easily.
12. From Williamson's
synthesis, preparation acidic among
:CHOH is most
is possible? CH=CH and C,H,OH.
of which of the following CH6, CH4.
ethers
(a) Only symmetrical 6. (a) CH,CH CH, CH,
OH
-

(b) Only asymmetrical ethers (1-butanol)

(c) Both (a) and (b) l alcohol
OH
(d) None of the above

13. Williamson's synthesis of preparing (b) CH CH ÇH CH, (c) CH,--CH

dimethyl ether is alan
(a) electrophilic sibstitution OH CH
(2-butanol) (2-methyl-2-propanol)
(b) Syl reaction 2 alcohol 3 alcohol
(c) electrophilic addition

reaction
(d) CH,CH-CH,OH
(d) Sy 2
reaction between
of the CH
14. The major product ethoxide is
chloride and sodium (2 methyl-1-propanol)
tert-butyl 1-butene
1° alcohol
2-methylprop-1-ene
(b)
(a) (d) ethene
(c) 2-butene
 Popers : CHEMiS
270 CBSE
Solved ISTRY
Chapterwise

The reactivity of Lucas reagent with alcohol OCH3

S>2>1°. i
fastest
Hence, 2-methyl-2-propanol reac
with Lucas 11.
7. Glycerol i
reagent.
generally used as an antifreeze reagent Anisole of ether is
and for name
making explosives. It is an ether and
the lUPAC
name is methov
8. so, its
Alcohols with same molecular weight are alkoxy
alkane.

to have almost same boiling point, however two expecteu given as

benzene.

more factors other than molecular weight are Williamson's synthesis, both symmetrical
mportant; they are namely H-bonding and surface 12. From
ethers can be prepared, e,
area of molecule. Both these factors are least in and asymmetrical
ethers
symmetrical
alcohols and maximum in synthesis of
1° alcohols.
Hence, 3 For
CH3OCH +NaBr
alcohols have least boiling point while 1° alcohols + CH3Br
CH0 Nat Dimcthyl ether
have maximum boiling point. Sodium Methyl (Symmetrical ether)
methoxide
bromide
s. Picric acid is 2,4,6- trinitro phenol
asymmetrical ethers
OH For synthesis of

CH3
CH
O2N NO2 CH-¢-O Na +CHBrCH-f-0-CH,

NO2 CH, CH
2,4,6-trinitrophenol Sodium lert-butaoxide Methyl tert-butyl ether
(asymmetrical ether)
10. Compounds containing either CH,CHOH or +NaBr

13. R-XONR-0-R
CH-Cgroup, when react with NaOH and1 Given equation represents Williamson synthesis.
form yellow coloured iodoform. This test is called
It involves nucleophilic substitution of the halide
iodoform test. CHOH contains neither CH,ÇH ion from the alkyl halide by the alkoxide ion by
S 2mechanism.
OH
14. Sodium ethoxide is a strong base, so it causes
dehydrohalogenation of 3° alkyl halide and gives
nor CH,C-group, thus it does not give
alkene.
iodoform test. CH
CH
Note The I, converts CH,0H into CH CH0. That's why it
gives iodoform test. CH-Cl +CH,ONa H,=a,
CHOH 2-methylprop-l-ene
CH
tert-butyl chloride

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