426 lxam idea Chemistry-XII _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ __

IMPORTANT QUESTIONS
[A] Remembering & Understanding-based Questions
Very Short Answer Questions (1
-
mark)
Q. 1. Suaest a reagent for convenlon of ethanol to ethanolc add. [NCERT Exe111plar]
Am. (i) Cr03 - H2SO.-, (ii) KMnOJOH-, (iii) (iv) Acidified KMn04 or K 2Br2~
Q. 2. What Is absolute alcohol?.
Ans. 100% ethyl alcohol is called absolute alcohol.
Q. 3. What • denatured alcohol? [NCERT Exe111plar]
Am. Alcohol is made unfit for drinking by mixing some copper sulphate and pyridine in it. This is called
denatured alcohol.
Q.4. Name the alkyl halide and sodium alkoxide used to synthesise tert-butyl ethyl ether.
Ans. ' tert-butoxide.
Ethyl bromide and sodium
Q.S. Of the two hydroxy organic compounds ROH and R'OH, the first one is basic and the other is adclic
in behaviour. How is R different from R'? •
Ans. R is an alkyl group whereas ·R' is an aryl group.
Q. 6. What is the order of dehydration of primary, secondary and tertiary alcohols?
Ans. Tertiary alcohols > Secondary alcohols > Primary alcohols.

Short Answer Questions (2, 3 marks)

Q. 1. Chmify the following as primary, secondary and tertiary alcohols: [NCERT]
CH3
I
(i) CH3-C-CH2OH (ii) H2C=CH-CH2O H
I
CH3

6
HO-CH-CH3
(iii) CHr-CJlr-CHr-O H (iv)

CH3
(v) ~CHr-fH-CH3 (vi) qYCH==C~- OH
OH . CH3
Ans. (i) Primary (ii) Primary
(iii) Primary (iv) Secondary
(v) Secondary (vi) Tertiary
Q. 2. Identify allylic alcohols in the above examples. [NCERT]
. CH3
vi ~-s:, , CH==CH-{--OH
( ) CH
3

Q. 3. Write the equations involved in the following reactions: [NCERTJ

(i) Reimer-~mann reaction
(ii) Kolbe's reaction
Refer to Basic Concepts Point 15. •

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 _ _ _ _ _,Alcohols, Phenols and Ethers 1427
:_ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

Q. 4. : . Explain the following wi~h an example: (i) Williamson ether synthesis (ii)
Umymmetrlcal ether. ·
• [NCERTJ
An& (1) Refer to Basic Concepts Point 15(v)
(i1) Unsymmetrical ether: If the alkyl or aryl groups attached to the·oxygen atom are
different, ethers are
called unsymmetrical ethers. For example, ethyl methyl ether, methyl phenyl ether, de.
Q. 5. Name the reagents used In the following reactions:
(i) Benzyl alcohol to benzolc acid.
(u) Dehydration or propan-2-ol to propene.
[NCERTJ
(iii) Oxidation of a primary alcohol to aldehyde.
(i) Acidified or alkaline potassium permanganate.
• I

Ans.
(ir) Cone. H2 SO4 at 433-443 K or 85% phosphoric acid at 443 K. ,
+
(iir) Pyridinium chlorochromate (PCC), C5H5 N HCICr03 in CH2Ch
' * • . ,'
[NCERTJ
Write equations of the (ollowing reactions:
1
Q.6. l • .- :.. ' ,

(i) Friedel-Crafts reaction -alkylat ion in anisole

(u) Nitration of anisole : • ~• .. :. ; . . . .i -~. ;, ,:,:·i •, ,·: '.' i -i :.
Ans. ,.
(i) Fri~ede~rafts reaction(Alkylation): ~ • _. • '
•
3 3
. ..' .

+ CH3Cl Anhyd. AICl3 Q H3 + .., .

CS2 ••
. 'I .. .
.
:\ ..... : :
. - .
,
2-Methoxytoluene CH3.
; ' ' .~
•

(Minor) •'
• 4-Methoxytoluene • : : 'J• • , • : • 1 '

•. •• • • • • , i (Maior) r
. .. i
I ' •' :,

(i,) Nitration of anisole: Anisole reacts with a mixture of concentrated sulphuric

and nitric acids to yield a
mixture of ortho and para nitroanisole. , . ._ :. . . ,l •
•••

.., . . ' ' .' :. -·.: ,;

OCH3 f.CH3 r

@• o-Nitroanisole
N02
(Minor) •
p-Nitroanisole
' (Major) , ,
. l

[NCERT].
Q. 7. Write equations of the following reactio~ :
(1) Bromination of anisole in ethanoic acid medium
• (u) Friedel-Crafts acetylation of anisole.
Ans. (,) Halogenation:

J"' f'
3

Br2 in Br
+
Ethanoic acid ~
Anisole o-Bromoanisole
Br '
(Minor)
p-Bromoanisole
(Major)

(u) Friedel-Crafts acetylation of anisole:

f.C"J .
I • "
(SJ + CH3COCI Anhyd. AICl 3 +
\

Ethanoyl 2-Methoxy
chloride acetophenone COCH3
(Minor) 4-Methoxy acetophenone
(Major)

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 430 \ xam idea Chemistry-Xll_..:....:..........-
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-----
Q.· 4. Ghe llradllnS ol the products you wou
ld expect when each of the following ako
HCI-ZnOi- bol reaa. "'-i
. -
(i) Batan-1-ol. [NCBlrJ
(ii) 2-Methylbutan-2-ol
Am. With HCl-ZnC2 (Lucas reagent): •
(i) cu3CH2CH CH 2- OH+ HCl , Anhyd. ZnCl:z No reaction at room temperature
2
Butan-1-ol (1°) (cone
.., .)
. : -· >: CH3 , . CH3 • ,
I •
;
• I
(ii) CH3 -C -. CH2CH3 + HCl .. ~.
. Anhyd. ZnCl 2 CI_J cI1 - CH CH + H 0
I :=t.,;;;_
(cone.) •
:IJ - 2 3 . 2
OH · · ..
2. Mdhylbutan . 2. ol · Cl • •
2- Chloro - 2 - methylbutane
Q.S . Che mid uie s of the produds you wou
ld expect when each of the following alcohol
(i) Batu-1-ol reacts with HBr.
• .• • (u) 2-Methylbutan-2-ol
(I) CH3CH2CH2CH 0H +. HBr Heat I [NCERT)
2 >CH3CH2 CH2CH2Br + H20 "
Butan -1-ol •
1-Bromobutane
: .
, CH l _;

. .. I .3.
J
. • I • I
, , ',. 0 •
CH3
"' t I
·- ;·.
#

(ii) CH3 ~ - ~2C H3

1...... u,. .... ~" , \
I,.- ~·
+ HBr Heat
I

' . .I . . .
.
> CH 3-C -CH 2C H3 + H20 •
.I /
• • • • •
f

OH.
- •

•
• ~. -~ ...._ ' )
I '
Br
2-~y lbu tan -2-o l ·'
• ~--. ... ' t

. • ~- •• • 2-Bromo-2-methylbutane 'l! ' -

J,......... . .\ '
Q.6 . Give structures of the produm
••
would expect when ~ch of the fol lo~ you
alcohol reads with soa 2.
'

(i) Butan-1-ol ·• •• ..

(ii) 2-Methylbutan-2-ol.
-
#

[NCERT]
•.··.·(I) CH3CH2Cll2CH <>H +
2 soa 2 .··,, .. Heat·· >CH Cli cu cu2·a + so + HCI
Butan -1-ol . • • •• •
3 2 2 2 · ·:
1- Chlorobutane
CH3
CHj ,,· • "
I . . Heat ·,1' ...-~
(i,) CH3 - C - CH2CH3 + SOC
l2
I > CH3·:..::..c.:....: cu~·cu3· + so2 + HCI
OH
I . l • '

2-Methylbutan -2 -ol Cl. • . .

2 - Chioro- 2 -methylbutane • . (.;• -1... - . •J. : '
•.. •
Q. 7. Ortbo and para-nitrophenols are more - , ,. ).

acidic than phenol. Draw the resonance

corresponding phenoxide ions. . structures of the
Ans. The resonance structures of o- and p-nitrop • [NC ERT , CBSE (Al) 2009) •'

henoxide ions and phenoxide ion' are give • t ~· • - , ,/

n as follows:

Resonance structures of o-nitrophenoxide

' ion . . • . ..
>

VI VD vm IX X
Resonance structures of p-nitrophenoxide ion
'

Xamldea
- - - - : - - - - - - - - - - - - - - - - - - - - - - Alcohols, Phenols and Ethers 1431

XI xn XIII XIV
Resonance structures of phenoxide ion

It is clear from the above structures that due to -R-effect of NO2 group, o-and p-nitrophenoxide ions are
more stable than phenoxide ion. Consequently, o- and p-nitrophenols are more acidic than phenol.
Q. 8. Write the IUPAC names of the following compounds: [NCERT]

CH3
I
(i) CH3 -CH - CH -C - CH3 (ii) CH3 - CH- CH2 - CH- CH - CH2CH3
I I I I I I
CH3 OH CH3 OH OH C2ffs

(iii) CH3 - ~H- CH3

OH OH
Am. (,) 2, 2, 4-Trimethylpentan-3-ol (ii) 5-Ethylheptane-2, 4-diol
(iil) Butane-2, 3-diol
Q. 9. Write the IUPAC names of the following compounds: [NCERT]
CH3
(I) HOCH2 -CHOH-CH20H (ii) &OH (iii)

Ans. . (,) Propane-I, 2, 3-triol (ii) 2-Methylphenol

(iii) 4-Methylphenol
Q.10. Write the IUPAC names of the- following compounds: [NCERT)
H3 H3
H
(,)
"-::
I /4
<..,,) "-::
I /4
H

(iii) CH3 - 0 - CH2 - CH - CH3

I
C"3
Ans. (i) 2, 5-Dimethylphenol (ii) 2, 6-Dimethylphenol
(iii) 1-Methoxy-2-methylpropane
Q.11. Write the IUPAC names of the following compounds: [NCERT)
(,) c,"5 - 0 - C2"5 (ii) c,"5 - 0 - C7H15
(iii) CH3CH2 - 0 - ~H-CH2CH3
C"3
Ans. (,) Ethoxybenz.ene (ii) 1-Phenoxyheptane
(iii) 2-Ethoxybutane
Q.12. Write the structures of the compounds whose IUPAC names are as follows: [NCERT]
(,) 1-Pbenylpropan-2-ol (ii) 3, S-Dimethylhexane-1, 3, S-triol
. (ii,) 2, 3-Diethylphenol

Xamldea
 4321 Xam idea C h e m i s t r y - X 1 1
-----------------------

Ans. (i) @-CH2-CHI -CH3

OH
CH3 CH3
I I 2Hs
(ii) CH 2 - CH 2 -C - CH2 -C - CH3 (iii)
I I I 2Hs
OH OH OH r
. ,.
Q. 13. Write the structures of the compound~ whose IUPA C names are as
follows:
(i) 1-Ethoxypropane (ii) 2-Ethoxy-3-methylpentane
(ii,) Cyclohexylmethanol
Ans. [NCERTJ
(i) CH3 CH2 O- CH2CH2CH3 (ii) CH3 -?H - F-C H2C H3

Cll:J C8i0 .Cll:J

rY H2OH'·
(iii) V ;

Q. 14. Write the structures of the comp

ounds whose IUPAC names are as follows: 1
(i) 3-Cyclohexylpentan-3-ol (ii) Cyclopent-3-en-1-ol
(iii) 3-Chloromethylpentan-1-ol.
[NCERT]

Ans. .i ' (i)

··, (i1) 6 I • I

(iii)

' .
Q. 1S.. ~a) Draw the structures of all isomeric alcoh
ols of molecular formula C H O and give their IUPA
It'.
'
.. ..
names. . • r. '•· .. ..
5 12 C
'
(b) C~i fy the isomers into primary, secon~ary and . l

tertiary alcohols. ..
[NCERTJ
Ans. Eight isomers are possible. These are: , . .~ ,.,._
OH
'
(i) CH3CH2CH2CH2CH2OH I
(ii) CH3CH2CH2 - CH- CH3
Pentan -1-ol (1 °)
Pentan -2-ol (2°) .
OH C"3 -
'·
I . -I .
(iii) CH3CH2 - CH- . CH2CH3 (iv) CH3CH2 -CH -CH 2OH
Pentan -3-ol (2°) .• : • ;· • 2-Methylbutan-1-ol (1°)

Cll:J
.. .
I I r
t
•
·J
(v) CH3 -
t

CH - CH2CH2 .__ OH - ,, . ''

3 - Methylbutan -1-ol (1 °)
.

2-Methylbutan -2-ol (3°)

CHj
l .
. '
.ri
Cll:J OH
I I I
(vii) CH3 -C - CH20H .... )
(viii) CH 1 -- CH - CH- CH
I . 3
. 3-Methylbutan -2-ol (2°)
CH3
. • . •r
l1 .
r
,
2. 2-Dimethylpropan -1-ol (1°) r I t •

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_ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Alcohols, Phenols and Ethers 1433

Q.16. Show how will you synthesise: [NCERT]

(1) 1-phenylethanol from a suitable alkene.
(ii) cyclohexylmethanol using an alkyl halide by an SN2 reaction.
(iii) pentane-1-ol using a suitable alkyl halide?
Ans. (1) Addition of H20 to cthenylbenzene in presence of dil. H2S04 gives 1-phenylethanol
~H=CHi Dil. H SO ~H-CH3
l-8) + H-OH
Ethenylbenzene
2 4
Mark. addition L8J 6H
1-Phenylethanol
I •
(ii) Hydrolysis of cyclohexylmethyl bromide by aqueous NaOH gives cyclohexylmethanol
H2Br cYH20H
+ NaOH Heat + NaBr
cY SN 2, Hydrolysis
Cyclohexylmethyl . Cyclohexylmethanol
bromide
(iii) Hydrolysis of 1-bromopentane by aqueous NaOH gives pentan~-1-ol.
Heat
CH3 - CH2 - CH2 - CH2 - CH2 - Br + NaOH
SN 2, Hydrolysis
.. 1- bromopentane • ', •• . , '

CH3CH2 - CH2 - CH2 -- CH2 - OH '+ NaBr

Pe~tane-1-ol ' •
.. , ...
• • Q.17. (,) Give the equations of reactions for the preparation of phenol from cumene. ,.
•
(ii) You are given benzene, cone. H2SO4 and NaOH. Write the equations for the preparation of phenol
using these reagents. • i •• - • • • • •• •
,, ' ..

(iii) Write the chemical reaction for the preparation of phenol from chlorobenzene. [NCERT]
• CH CH •
I 3 I 3 · .
CH:r-(;H
@ CHrC-0-0-H •
@, .
I rf'

o,
; I

Ans. (i)
Cumene Cumene hydroperoxide
;
. ,
- +
: .,
ONa OH

(ii) ©
Benzene
cone. H2S04
fl.
~,H

Benzene
NaOH, fuse
L73 K @
Sodium
H2S04
@
Phenol '
sulphonic acid phenoxide

~a+ ' HCI

623 K
(iii) +NaOH
300 atm

Q. 18. Give reasons for the following observations.

(i) Propanol has higher boiling point than that of the hydrocarbon, butane.
(ii) Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular
, '

Ans. (,) The molecules of butane are held together by weak van der Waal's forces of attraction while those of
propanol are held together by stronger intermolecular hydrogen bonds.
o+ o- o+ o- o+ o-
............ H- 0 .......... H- 0 ............. H- 0 ............... .

Hence, the boiling point of propanol is much higher than that of butane.

ia1nidea1
 "'II

4341 Xam idea Chemistry-XII _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ __

(ii) Alcohols can fonn H-bonds with water and break the H-bonds already existing between water
molecules. Hence, they are soluble in water.
o- o+ o- o+ o-
R- 0 ......... H- 0 ........ H- 0 ....... .

" H
" H
"' R
In contrast, hydrocarbons cannot form H-bonds with water and hence are insoluble in water.
Q. 19. Give the structures and IUPAC names of monohydric phenols of molecular formula, C7H80.
[NCERT]
Ans. The three isomers are given as follows:

~H3 oH-@-CH3
2-Methylphenol H3
or o-Cresol 3-Methylphenol 4-Methylphenol
or m-Cresol or p-Cresol

Q. 20. Explain how does -OH group attached to a carbon of benzene ring activate it towards electrophilic
substitution. [NCERTj
Ans. Phenol may be regarded as a resonance hybrid of following structures.
••

~o
•• •• •• ••

CT· q5. c6.

c:.oH +OH +OH c:_oH :OH

.. • I ,.
. G·-
I II III IV V
Thus, due to +R-effect of the -OH group, the electron density in the benzene ring increases thereby facilitating
the attack of an electrophile. In other words, presence of -OH group, activates the benzene ring towards
electrophilic substitution reactions. Now, since the electron density is relatively higher at the two o- and one
p-position, electrophilic substitution occurs mainly at o- and p-positions.
Q. 21. Give two reactions that s~ow the acidic nature of phenol. Compare acidity of phenol with that of
ethanol. [NCERT, CBSE (Al) 2009]
Ans. The reactions showing a~idic nature of phenol are:
(i) Reaction with sodium: Phenol reacts with active metals like sodium to liberate H2 gas.
,1" ONa

2Q + 2Na 26 + H2
Phenol Sodium
pheooxide

(ii) Reaction with NaOH: Phenol dissolves in NaOH to form sodium phenoxide ancfwater.
fH 1.Na
Q +NaOH --- Q + H20
Phenol Sodium phenoxide '
Comparison of addic character of phenol and ethanol: ~henol is more acidic than ethanol. This is due to
the reason that phenoxide ion left after the loss of a proton from phenol is stabilised by resonance while

··-
ethoxide ion left after loss of a proton from ethanol is not stabilised by resonance.
:o•• ••
:o ••
:o.) . ·o· ··-
;§. ~4 . cg . t) .
··-
• •

. ..
I II Ill IV V

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:. •· • • lcohols, Phenols and Ethers 1435

Q.22. Give equations of the following reactions:

(i) Oxidation of propan-1-ol with alkali~~ KMn04 iolutlon. :
(ii) Bromine In CS2 with phenol.
' :.
.
' .
.,,
.

. ..
'J

. • /'.

__
, ,I

C
_(.
':

1' :
\
[NCERT]
,.>.:,r/ ! .

Am. (1) CH3CH2CH20H + 2 [0] Atk. KMno4 (Oxidation) CH3CH2COOH + H20

@ ·-
Propan -1-ol
1
'_ u+ /H 20 PropanoiclCid
tff

(ii)
-B
r2
cs2
.. .
111
~•"\
, L'
c& Br ., .,1 i
- a• • ·~--,- +
.·, • ,,

I •t·, , '
.,
Phenol - : , ·-·. : • ' o-Bromophenol : • l /

•, _ :· . . •• • •. • -r.: •., . . - (Minor product) Br • !- • - ~- _. - '

" .1- .. .• JI , •

. ,.
.!_.., :t·, ,,·,. -~ J •· , .._.. ·--~-~

.. -.,
r_ -·
p-Bromophenol
l ' • 1" ,.F,
,
"Jt
•
•~.,..i__..... , t" !-~;1.,<
...... c. . ;.."';
J·!.;; (Major product)
\, I. • • ..
' ,, • :..1 • I

Q. 23. l Give equations of the following ~ctions: [NCERT]

l ,-~
(i) Dilute nitric add with phenol. :"'1.

'. ·-~ .

c& . . '.· . . .-~ . ·:· •" ..., ......... -. ·-~,'

;

(ii) Treating phenol with chloroform in presence of aqueous NaOH. _ , .., .. :~ ... _.

@ -.
!,,·,,-,
·. i·, . OH . . ''• .. '..... ) ~-, .. -· ... f'/ ..,t-1 ,,,,,,, 4\
:l
!) t, -,-~ l - •' ( \ • _: _) ! - •.... : 1 .,. 1 • .. ,. • .. .,

Dil.HN03,.:. ,•;;,t,
Ans. '. (1) • ··l ·'-··
N?2 J .• .... ,.__ ::.,\ --·:•:: ,,!

0 -.. , '• •: j '

•
! r
.!,..
·.-•
•
• ,•
, 0 • : (
• ..
•,•
-
f+
•
•
_....
......- /
""V' "'!
,. ;
a.

Phenol o-Nitrophenol . N02 ! ,\ '

.. t , r J.
''t,. •

@e . -··':,·
/
p-Nitrophenol . •.

''
c&a ,:·~-: ;. :~
; •• •\._
•·· ft -., ... • ' .;. l • I• .: •• ... - - ' ' '
H .:r:""':•.,'.,; t!" •••::rt-f:>,..~?-:• \s·f•>
I

,;: t t,1~· ·.1. ,:c·:" .,

. ,. T ;

.•.' .
1·:_•. • CHO -• 0 i;- ,J,
(. CHC13, NaOH, 343 K . W, H20
U O · (Reimer-Tiemann reaction) ,;1 0 .',~) ----~ ~_;. 0 ; ·,_,, ::. S•'(r,:.i.. ~-: ! •; • .-,:
.. '\,.
<
: -" Phenol , '
·, ••• ~' , - -• • • .

..,.:,,\:!.:_ 1,it'if.J!.··.,·'.'tl ...~,!i1l.,Jj..

., / • ·• • . i" •• ; Salicylaldehyde
•
1. !
·; e·!~. :t.-.t•t.,t·.!.
,., • • •
• •"\" ·;i

,, ~- ..,,,..,, ¼• -~••~•,• •••·• ,....., ,- C - )',t • ' • (Ma.)Ol'pr~t), . . 0

Y.:'l~·~•:
,;.,"',- .,.'!/fr>.! • .t'>"t'1•"ll•· ..,. ' : • : t , , ' , , \ ,• -t •11:. t • :~ 1 . ; 0 : •• • '/ ~-. ,'4 ~.,• ~: u--.;." 1,.; ••
!.• ,, ... ,.
•"
..
• ~- • -,

..,,... ••· .-.f ••' '"•

\t' ''"', •.,,. " ·, . . , '• .,!- t\lJ • J

-, • : .\ A small amount of p-hydroxybenzaldehyde ~s also formed._ :>:,.I'.::..,.),

?c_·\, ·;. •. ; ~-•.'-; ., :~•.. - . ,· \ .
..• •~·"'" ,i._i_.~_._.\ J -•- _,,.,' - .• , , . ,.,: I •
1
.f4'
•-

Q. 24. How are the following conversions carried out? ;-~·,.·. ·- _, ~· , ,, . . .-. [NCERT)
(i) Propene. Propan-2-ol ..... • .. ,
. '.

(ii) Benzyl chloride Benzyl alcohol ----+ . ft'.'ft;

' .,

Ans. (1) Propan-2-ol can be prepared from propene_ by hydration as shown below:- • .. 1 • : '1" } l"' ,· .. ,\.
\' •,,.,
-~.:.,
CH3 - CH= CH2 + cone. H2S04 CH3 -CH~CH3
I . . , .. ·:~
..
c.:.J. ,,,:;;':).; ,,
t
-; .4.-,-.,.!.. , Propene 1,:# •" .
.. ).

OS03H
t .

.•!
.
I. . !' \ ... t

lsopropyl hydrogen sulphate .-~~·• ; r

CH3 - CH- CH3 + H20

. . B~

.
CH3 -i-
. CH3 I J ' .
+ H2S04 ) •.
/I ., '
.
"J
c•
• f. ,Jc·!...
I .H ,. • • • . , . • ·• ' ' I ., A , , I ' • \ : ·'

•. ... "((''" OH .,l ,,·,,· .,,·,' •£

Oso •
&•! • ' , _ .

..
of .... • •

3
$ I .- T" L- I

Propan -2- ol ,.:,

t ,i j _l '
fH 0H
'· j,'_~ ll
;,,
t. t
'..:!r •~ ·.,;1 2
~2a

(ii) + NaOH (aq)

Hydrolysis
(8) + NaCl ·c-• ·r· t ·:
•• ' •

.
l •

Benzyl chloride Benzyl alcohol ~~f.l

I i 1
I " J
,-"
Q. 25. How are the following conversions carried out?
.......
[NCERT]
fH,- ·• :;\' J,: L;:,,?.
(i) Ethyl magnesium chloride ·:.: .:-' >Propan-1-ol '••
,,.,• ... •l
\
.,
',, '; 1 •
(ii) Methyl magnesium bromide >2-Methylpropan-2-ol
f,;"
},,
'-t"' ,r -;-..,,.... ,.
,.,_.,_2 • .;1t1•y,;,·~
, +.1
, ...
i

lam/de,
 4361 Xam idea Ch em ist ry- Xll --- --- ---
--- -~ --- --- :-- --

H '-.+& () -6 6+ Dry th
Am. (i} • ~=O + CH3 _C H2 - Mg Cl e er . [CH:;CH2CH20MgCI]
H/ Ethyl magnesium chloride Addition product ,.,,
•.1· ]1 1·•
Methanal
H20IH + CH 3CH 2CH20H + Mg(OH)Q
Hydrolysis Propan -1- ol
CH ('. CH3 " / CH3
3 "+6 \ •~6 6- 6+ Dry ether
(i1) /C= O + CH3 -Mg Br C -· /

CH3 CH3 / '-. OMgBr

Propanone or Acetone Addition product
CH3 CH3
H 20/H+ "
,- C/
Hydrolysis / " - + Mg(OH)Br
CH3 OH
2 -Methylpropan -2- ol
.,
Q.26. Give the IUPAC names of the following ethers ./
:
(i) C21fsOCH2 - ~H- CH3 (ii) CH30CH2CH2CI •
CH3 · • -

(iii) • ~·

,,
Am. (i) 1-Ethoxy-2-methylpropane , • •• (ii) 2-Chloro-1-methoxyethane .,1! .,_t~•
• (iii) l-Ethoxy-4, 4-dimethylcyclohexane -
! ...... •

Q. 27. Give the IUPAC names of the following ethers:

[NC'Eff)
(i) 02N - C,H4 - OCH3 (p) '; 'f•.••
·, ',\
.. (ii). CH3CH2CH20CH3:
':I,, ,,.

"''" 'D'~ .<I

-! •..J -=~-,., ·,
..
•

~-
,__

,s • • (iii) ~2" 5 ..
I••

1. .:'vi:. , .. <·:
Am. (i) 4-Nitroanisole (ii) 1-Methoxypropane J ·-• k1.-· ~; i :-:'0 ,-l t
(iii) Ethoxybenzene -1 . ..·
(

Q. 28. Write the names of reagents and equations

for the preparation of the following ethers lty
Williamson's synthesis:
[NCER1J
(i) 1-P rop oxy pro p~ ( ) Eth oxy ~:: ii•:\ . , , . _ _ .
Ans. (i) CH3CH2CH O-Na + CH3CH2CH2 - Br
2 •••
Sodium propoxide 1-Bromopropane

_ Heat > CH3CH2CH2 - 0 - CH CH CH3 + NaBr

d~ • n 1 2 2
1-Propoxypropane

(ii)
@a• + CH3CH2~r _ ·11__,...
; . ~H2CH3
0 r
t

·+ NaBr
' t .... ,,
:,.. ,_

Sodium phenoxide
, . .
Bromoethane : Ethoxybemene ....
, ,;

Q. 29. Write the names of reagents and equations for the preparation of· the
following etben bJ
Williamson's synthesis:
(i) 2-Methyl-2-methoxypropane
'•'J_..... "::/ (NCEllTJ I ·- : > a• ·- • ~ :\

(ii) 1-Metboxyetbane

~J
~-- Aarn1.dea.
 t

I Alcohols, Phenols and Ethers 143; •

,;
. .. '
' I ,.. f: 1
CH3. • . . .: . . CH3 ]'
.· ··· . n,
I .-~
•( •
I •
I
. , I

ri;.~;l.,:
...
- . ; t
I •-.I•- 1

A• (I) CH3,·-C-O-Na+; + CH 3 - Br Heat • CH3 -C - OCH3 • + NaBr

I Bromomethane I !
., ., ,:~"r.
I
CH3 • I . • , oi .... !'I> CH3 J: , ........

#-_~ 't

.. •. • • • • •/:\_. • , •.... • • 2-Methyl-2-methoxypropane ... ,"l,

,.,
.. _ ·"'•
f . \ ., ! " . .. . ,! :.tl,l'
f •
'
;•7~__;,., (i1) CH3CH20-Na+ + CH3 - Br Heat .~,. CH3CH 2 - 0 - CH3 +, NaBr .,_;!, \·.:;;
Sodium ethoxide Bromomethane •-• ., · 1- Methoxyethane • •
1•,.
•
. .. ,.,-,.
•.
r
' ~- .
•. -. 'Ii ..
'
Q. 30. 1-propoxypropane synthesised fromipropa~•l-ol? _.! 1.~:·.,~!I,.: ,_; t:i·.. /:frfq ·:: 1
.. 1 [i•I. 1 ;. [NCERTJ
'•·
-.- :'!,.: ,·. .,. ...1 ·,.. . . . . , ...
Ans. . The following two methods can be used: ... ..·, ..... , .......~.i.~:,....._: ~_:;,_. • ._,;._ ·--~~~ .. ~-..,_-1-LJ :.~\_...:· \.L_~ .1°1• _!.1_1

• (a) Wllluumon's synthesis . ,· .... ..... . ' (· •

• • I, t l
¥, -.
i
,
•
• • • •,
.• f .
.Ji, __ • ,- .... . 1 "
I' • ... • . • •
....
! •
I!\•I• /•;

:· __. ,.. ·., (I) 3 CH3CH2CH20H + PBr; ~ - 3 CH3CH2Cff2B; .+ H3P03 ,.~ :~ .:~ - 1
),.::,_ L~.
Propan -1-ol 1- Bromopropane , .. . . . ....
-• r •i d ...~.
:, .. ,. • , i; .r-' • • 4 .._ .J , •••_.

,1;·J1.·: .·:,~ .. (ii) 3CH3CH2CH20H+ 2Na 2CH3CH2CH20-Na+ t H2 .-'·. ,:·;,;:1.:·~.-:__:.~t}l r "::

Propan -1-ol r •
... Sodium propo:Xide 1 1,·<.-~, :. ..•,,.
---. • 1
,-,~·-,,·.;-. -,i,;.-•::·,-..
> ,.·,•L ' ·' ,- • . •l''" •.•

~~.:\ .c-_.•4-
Dry ether . , ·'(Y.:_..-.;.!
2 -Na + + CH3 CH2 CH2 - ~Br
·1 ,r;- ·, -., ...,.,. " s= ,-i.
3 2 CH CH CH 0 ·"' i L,_ i.:.._.....,J •., ,. .,4 •• ·'.·''

Heat • ··.1
• • • • • ,. ~~,.-.l :-• \
.... -~ ,. .. ' 'i
,;t ,
k,~...

,c.. .:. CH3CH2CH2 -. 0~ CH2CH2CH3. -t: NaB~c r~~>

. .. 1- Propoxypropane _ . , , ,L . _ _-;•t ,, :.• •..
I
;, =-~ ;~. " ! f, -- ' ,. .... ~' • ~n .l!jf'f (rt) ~n-'_·c•·!:.\ ~' •.h•

u ;.~·tl, (b) B~_dehydntionofl-propanolw ithconc.H2S04 at_~l3~ •. ;-•i:.;;ir,):,,·, .r:•L·i,f•n:,•.-;f ff) ~tt: t·

2CH3CH2CH20H cone. 82504 > CH3CH2CH2 - 0 CH2CH2CHf··-+ H20
;;-,.,,.,l- . .-·,-, hrr ,' , , · , . . ' ·. , . ,•. i-:.: ;. , 413 K ..(~:- r,:. ' . .., ·; 1-Propoxypropane , ·l , ,: , ,-, , ' ) , •••
. . . . . . . . .,4L...-:·"·''',J ~-,J,J~1•,-. I ...- • ..... l,~-··:·-.·-·•.''"•:t - 1 ..., - . :. j' • J.!')'~-t ,,-,.~ 1( , . ' - , - · ...•,;,_•) . ) ' " • • ~..... • ,~}

.
Q. 31. Prepantion pf ethers by acid-catalysed dehydration of secondary and tertiary alcohols is not a
' · . . .-·· SIil·table IDetbod. G.IVe re8SOD. : ' ' . . •. ·' ''·.. ·•• .'· . : -:.··.• •··".· _' .•·- : •. ' -, •'-' ··_· •·. •• ' [·uc'
I'Y' 11.,....
J u • r
j
- - -
' •
•• • &:,n•
,.. . . •* • -

Ans. Acid-catalysed dehydration ·of primary alcohols to. ethers occurs by SN2 reaction involving nucleophilic
attack of the alcohol mo~e on the protonated alcohol molecule. 1',. • .... )r' ·:_.; c, '. - ..i ; ' •
•

. r

• •
1 ,'., ·r.· ,,,.~-·;.,)t,• '-~ ·•· '·,l
,-,,_,,. · ,.. '-•:•' ... ,,,,._·\l~,.• .• ,,. 1~, .. .\._,J •. J-~, ,_,
. r· ' .. ',• + I •.,. .,. ., ~G:,-.:t11.'\ ..... : .~~,"
1,,.-:,.'
·~..1..
J,

,i:,_tr·, ... : •• .Ir

CH3CH2CH2 0 H +-CH3CH2CH2 -. OH2 • :p1·rrr1 , :,; f>";•:••d·, ; ... ~r,• -'i•' f, -:..:',.-,;~, ,1'-
•. I'•-""'• • C.- •~'f .,_1• ,.,.~•.;_;. ";.. .... ~., .}
0

,.. ....,t_._ ~ - .: ..,,!_~'...Jr,"?..,_.... \ •t'

~-,.n ~i ,:.:,:, ·.:..,:r:~:-~;d.-_1 ;,:!;r;, {°;~y;,.:-~,:f:· s· 2 :,'.~•:.•,,,:~ :h•• > • t:;,-: • • -!.;-J- . • .. : ! "~·:

, • .. -.. •\ ·,·t,·;1:\"l',, ·''- N

H20
> CH3CH2CH2 - 0 - CH2CH2CH3
• • •
l, 11\..,.,,.sJ•••-" •• ''---·'· • r .!, -

r: _ ;.J; ·• 1- Under these co~ditions, secondary and tertiary alcohols, however, gi~e alke~ rather than ethers.. This is
because due to steric hindrance, nucleophilic attack of the alcohol molecule on the protonated alcohol ,
molecule does not occur. Instead, protonated secondary and tertiary alcohols lose a molecule of water to form
stable secondary and tertiary carbocations. These carbocations prefer to lose a proton to form alkenes rather
than undergoing nucleophilic attack by alcohol molecule to form ethers.., •.;.., _-;~ ~? " • . !/ 'I!; .. ?. ., ;,: l
,r·ri··. •. ~ • .... \.; r'
,,_ '·
,.{J ..,\,
'
j:

8
CR.

1
--:3

CH3-CH- OH---CH3-Cff.-:. 0 H2 . '

-•--••t
..
1· • .,

; •
It. t
"

-
CH-

1
&~

r ,·

+ • _· •. \
-
ir ·,.
:, ' - • ~ : , _ ..111
,II··,

: •
,' ·-
I''
·t.; -~•·--t
.,_,

CH3-CW
,,
L.:...J:

_
("I.I_
"""·--:3
1

It. Propan-2-ol • • •• • ~--.• .,.-: H20, lsopropyl carboclbOII i . , .

(2o Alcohol) Protonated propan - 2-ol ·-·••'-; (2 o Carbocation) • -. ••l
. ,:";. ,'..,}
' "

c~ .
~I
. .. c~
•••• I
·- 1-

I ••
_, .... .,,,

CH3-CH- 0-CH-CH ~CH1CH~HCH1

I
t ... •c~,,
.1 • ..... .
•• 3 "7'\
CH3-CH-t -u+ CH3-CH=~
_9+
.,
·.:. -~--.;
. Propene .f'..
2-Propoxy-2-propane
j
Similarly, tertiary alcohols give alkenes rather than ethers. i
·':':~
• . +ff+ •
(CH3)3C-OH • . > (CH3)3C-OH2 _ ____.(CH3)3C+
•• -HO
2 ""__ ..
2- Mdhylpropan -2 -ol ., , tert - Butyl _1J _.: t
(3° Alcohol) Protonated •• carbocatioo ·_._ •"· ,.<
2- Methylpropan -2-ol

'
 438 lxam idea C h e m i s t r y - X I I - - - - -
-~-~------------

f'3 .. l°3.
CH3 -C- O-C -CH 3
~(CH, >,C$: iH
CH3 -=-C+ · ---+ CH3 -
f83 f13
C= CH2
- I ·~- I , -H•
.' I - H+ 2- Methylprop-1- ene
C"3 ("3 ("3'
2-Methyl -2-(2- methyl - .tert -Butyl
2-propoxy) propane carbocation
I

Q.32. Give reasom for the following: , .. 4

(i) Alcohok are more soluble In water than the hydro
carbons of comparable molecular masae..
,~#,' 1-, [CBSE (AI) 20J;
(a) Lower alcohols are soluble In water, higher alcohols
•

1 ,
i • \ .. '-r
are not.
(iii) Ortbo-nitrophenol is more acidic than ortho-metho
xyphe nol: •. • ,, •;· : [CBSE (Al) 2
Am. (I) This is due to the ability of alcohols to form hydrogen bonds with water
1

molecules.
(i1) Lower alcohols can form H-bonds with water where
as higher alcohols cannot due to
hydrocarbons part.
•
l•.? • :· .. • (iii) It is because nitro group is electron
withdrawing which increases the acidic character whereas -
group is electron releasing which decreases acidic character.
Q • 33. A .......vun
- t ,or
• the •,onowmg • : . _. ·, _·. .............
· ~:,,, ~,~- . ,., " f -_. ..,
f : · ., • l
1
! ,,. J

(i) 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.
Am. (I) Rectified spirit containing 95% ethyl alcohol and 5% water
fonns an azeotropic mixture which distils
0 , i 1 a constant temperature of 351.13 K., -; . ; :
·• ~" (ii) Since diethyl ether does not contain an active hydrogen
attached to oxygen like alcohols and phenols, k
,, ~· . ,- .,, .
•
. does not react with sodium. - . _ . .1 ,
' .... ._. • • . . . -;. •
·' ' - - . ,: ' , •
r-r},.'j :, •(iii) The C-0 bond in phenols has some double bond
' .
t\
•
'; • I"\

character due to resonance and hence cannot~ eai1y

. •·

·.,·.k~.,-··1._-:, ,.,_,., cleaved by nucleophile. In contrast, the C-0 bond

in alcohols is a pure single bond ~d hence canbt
·- easily cleaved by nucleophile. ,'',!:t•. ;c....,, f~•
,ziii '.iJ' i;, ~•;r;'.:!!
1~ , ' , , -~- :i . . : '. , , . .

:.. Q. 34. Answer the following questions:

-... (i) Dipole moment of phenol is smaller that that of metha
nol. Why? •' , ; :..) 1 .!• .,
(ii) In Kolbe's reaction, instead of phenol, phenoxide ion
is treated with carbon dioxide. Why?
[NCERT &-,l lr)
• ; - " ' I

Am. , ,• (1) In phenol, C-:--0 bond is less polar due to electron-with

drawing effect of benzene ring whereas ia
, , • :: J ·-~:~ meth~ol, C;-0 bond is more polar due to electron-releasing effect
of -CH3 group. , ., . ,.
,_

n'•·z.~~rt:i,5 (ii) Phenoxide ion is more reactive than phenol ._

towards electrophilic aromatic substitution and bencl
·, • 1; ·, •••z ,, • •, undergoes electrophilic substitution with carbon
dioxide which is a weak electrophile. _. <! .• ,.,,.. • •
Q. 35. (i) Write the IUPAC name of the following compound:
. .. --~· •",· .. ;- -~ ~-H r.·-~i- 1 1
1
• CHr -0--C Hr-fH -CH3 . itr--, [CBSE(F)2012)
{~·, . .y . -· -.. C_H3 p
. ,.,. 1--t

(ii) Draw the struct ure of 2, 6-dimethylphenoL .

[CBSE(Al)2011) 'l
(iii) Suggest a reagent for the following conversion: I,

......
OH 9 .: '
)
~.>

-~· ,
,;: -~ Nv .... •

·\~.
0

[NCERT Br-,, ,.,)

•

'
Ans. (i) 1-methoxy-2-methyl propane.
~'-~. ! '

. , • f ·r.
., -, •
(ii) H 3 C i f3. ,.
. -.~
, I
, •. ,· "";": ,.
•= , ! 1 ! •
,,.,
(iii) Cr0 , Pyridine and HCl (Pyridinium chlorochromate) \
3
,. .,

• a-a::i
L - - - - - - - : - - - - - - - - ~ - - - - - - - - - A l c o h o l s , Phenols and Ethers 1439
'

Q.36. Answer the following questions: 1--- : :, ...,.f .. i_,..

, , L, ( .'

If i .J l ' i._ .\;'.~ . , ....

(,) Why are ethen insoluble In water? _;>~•"..'

.,,. ::
(uj Complete the reaction equation:
J"

· ? ,, · · V't'V
\.
. A
- 9!!
(iii) How will you know whether a given OH group Is alcoholic or phenolic In nature?
Am. (1) Ethers are insoluble in water because due to the bigger size of the alkyl groups, the oxygen atom in ethers
fails to form intermolecular ff-bonds with water.

(ii) '\A('v H2Om+

4-Methylhept-3-ene 4-Methylheptan-4-ol

(iii) Phenolic OH group gives blue or violet colouration with neutral FeCl 3 , while alcoholic OH group does not
Q. 37. Give a chemical test to distinguish between the following pairs of compounds.

0 6
OH 20H
t !
•
,_, '
11 ) ' •~
!
• ..
• •. , r
• • • 4 ; ,·r;
,
.•
.~
•-..
._.,.. L• ,
- >t
'•'- ..
I
j

and (ii) CH3-CH-CH 3 ,',.r,·

bH ' . ,. '
rt; i
(I) ~
i I•, 1[ ........
'-, )t /' (
.• j .
,.
.. ' • -
,.:
. ..:
.. • -· · .•·; 1•
- I '\ . ' • • ., •,.' I'
1 ....

Am. (i) Phenol gives violet colouration with FeC13 solutfon while cyclohexanol does not.
~ 5OH ~+ FeC13 . ~- [Fe(OC6"5)6]3- + 3W + 3HCI 1

Phenol Violet colouration , '.

'

• f;, .....
,I

··~ i _'·/
/" .
6
Cyclohexanol . ;
FeCl3
No violet colouration

(ii) Isopropyl alcohol when wanned with NaOI (12/NaOH) gives yellow precipitate of iodoform, in contrast j

benzyl alcohol does not respond to iodofonn test. , ~•,,'

' ;'• ... •,..;,

+NaOI • CH -C-CH +3Na0I

CH3-C-C-l3
• , ••
CHr-fH-CH3
OH
- Nal
-H20 -,
3 II
() •
3
•
-3 NaOH
.. A ·'•-!,_ • ;
,t

Isopropyl
alcohol .+
CHI3
l ,,..
'.' I
. •
-+

.. f
,.;, .,
,; C•

_
/
,, t,.?
.'
..\,.•

,_
Iodoform
. ;•,, •• ":fl· (Yellowppt.) · ·:t.:~i __ ; ·, .

Q. 38. Give chemical tests to distinguish between compounds in each of the following pairs: . • t ; I • lI I
. ' t '

(i) Phenol and benzyl alcohol

• •• _.1 .: . ., 1 L11, •. :1 i·• • ;\ .. ,·. -~ ;-•_ .. ,.-..~:; •
(u) Butan-2-ol and 2 Methylpropan-2 -ol •
.·,.·LI

Ans. (1) Phenol gives a violet colouration with FeC13 solution while benzyl alcohol does not. .. , .•,,.
,:, /· ..... - t
_.,,.11 .-
;, :•,

6C6"5OH + FeC13 i : • > [(C6H5O)~e]3- -+ 3HC1 , + 3W.-. r-:-< • 1

l
' '•

, Violet colouration l J/1 ' i\ ,-'. :t·~ ,;;_;_I\

(ii) Butan-2-ol when wanned with NaOI (12/NaOH) gives yellow precipitate of iodoform while
2-methylpropan-2-ol does not give this test.

?" A
CH3CH2CHCH3 + 412 + 6NaOH - - CHI3 + CH3CH2COONa + 5Nal + SH2O
-+

lodoform

(CH3))COH + 12 + NaOH - - No reaction

Xam/de,
 I
440 Xam idea Chemistry-XII _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ ___

Q. 39. Alcohols react bo~ as nucleophiles as well as electrophiles. Write ~ne reaction of each type·
11111
describe its mechamsm. . ' , . [CBSE (Al) 2008] >• .• _(._

Am. Alcohols u nucleophiles: The bond between 0-H is broken when alcohols react as nucleophiles.

-~+
R-0-H + "-c- . " . ' . ;
".. •• f
y
'.
r I+.+ {
R . .. -. .. _- . ~-
'
•
> •

-~
4 -. -+: H,
+
'·... '
,. " .
.
... ., .. ;;; 1' -! ..,-; , . ' ,, 1 .

' •.: •-- Alcohols u electrophlles: The bond C-0 is broken when alcohols react as electrophiles. Proton~
- alcohols react in this manner. •• •
•• . + . +
R-CH2-0-H + H _ ___,. 1R--CH2-0H2 ~I

•• ••
- - (,+ ~-....f•_~' -... r •• •t ,•:,,--: .,
I ''•

, L_: I ; -~':.,I' . {: : l ,r .
Br + ~H2~H2 __ ,,:;;,, Br0H2 .~-,~~g ,,

R . ,·: ,- .- t R .. ,
·.~,.~> •(Electrophile) ·~
.J .... "
,tr~~:,:;',.:.•:r.# ;,,(.!
1
i~., -~.-.;,.:-:~:(
.a
1
~;;-1,..•.~-ti,
, ·_ ••

!"• ,;, l'

1,·'
.J C ~:; ,.,. ·1 : .,( 4
~., :. "

~I•',, ·: •.
·., •-·
... ',-• ._{~

Q. 40. • How would you carry out the following conversions?

(i) Ethyl magnesium chloride to propan-1-ol . .
...,,.
, I~-·, 1•"'l;

(a') Benzyl chloride to benzyl alcohol , [CBSE (Al) 2008]

0- ~- !_i ~•-:,/ :r '::~·!,~-{:\. ·.. "'- ·.• ·,·}·: t•'· ,~:i ,l, OMgCI /\ . - ~if.

II ·-,, .... ,..

·f.,;,~. -~· ....... J, • .,
6. - )~
6+. _, .,·~;·.~
,,.. ... - I J,·,, i ;• Fl <

Am.
' J •
(1) H-C-H ·.,...·. CH3 -CH2-· MgCl - > H-C-H
Formaldehyde • ' Ethyl magnesium .I '.1.'j

l :. "' chloride .. ~./,

CH2-··cu3
........
, .
~·'.•~ ~t ·:
'
"'1
,,. _

I
':-"' ..,..
OH
820
CH3 -CH2 -CH2·-0H ,·) + Mg/
.:... J:. •.

, •
}~Ji..._ ,· •
I ,... #J,. _,,__,,.
..
;
.,!,.'
• ~ - "• '
1'.., 1 •
• '!
: .•
~.,_!~)...:.
)1
·~t:
I '
•
l
•:· ·:- t, ,i • .•~ . 1
.. ,\ ,•;
',•..,. ~->','
·,1·,-:·}· ,.,,:_.i'. .. ..
JI . •
Propan-1-ol .. '".,
-
• - .c,, l
.•
1 •,,~~ri

' -a·

@
.'i,::~,, .. CH ·_ ,; i -_;(J.'rt-,-2,I, ..
~ I , .....
2~· '-' . 08
.
@-
2
-,,....}''-1.;,
I- :J i . . .. -,
•
.
..
..
'-:~--· l,1.~__,.\.·
.. .• .• •
,-..~-·
. i' I·•
- ~.
• .....
-'•' , r .._ \
.... . • •• ,. ·--ft! )
}• _. ; .-:_·. + KCI
. ' .

(u) _ • )~ KOH (aq>° ·_ • ·? A

_- ' -· .-.
..
Bcazyl chloride 1• • Benzyl alcohol •(

•• f '

Q. 41. The carboD-OXfgen bond in phenol is slightly stronger than that in methanol. Why?
Ans.. This is due to the fact that - •• • " , .,.. . . .
(1) in phenol, C9njugati.on of unshared electron pair over oxygen with aromatic ring results in partial double
bond character in carbo~xygen ~nd. . . . . , : •;. _ . ,.: . . - r • , , • • • • : • •

2 3
(ii) in phenol, oxygen is attached to a sp hybridis'ed carbon atom while i~ m~than~l, it is ~ttac~ t~ a sp
hybridised carbon atom. The bond fonned between oxygen and sp2 hybridised carbon is more stable
than that fonned between oxygen and sp3 hybridised carbon. • ·_ . ••• H ~:- : • _,.. • ,. • ·.; •
' t .. .. •

Q. 42. Ethen can be prepared by Williamson synthesis in which an alkyl halide k reacted with sodium
alkonde. tert-butyl ether cannot be prepared by this method. Explain. 1 d • ·, ::- . . )~-
Ans. In tat-butyl halides, elimination is favoured over substitution, so>.alkene is the only reaction product and •
• not &
.-.L.- IS I \JI-IIJIIC;\I.
- ~ : . ... · .... · t·- ' . , ;. . ". ' f ,
I
I • ' • , ' • • ' • ', '~
,, '.i r-
, .
l . • f ' r • I • r.. •• ' • • r - .) I JI " ' \ , • • • ) : t .... ' '

~+Br + N:0C~(CH~3 CH3~~ ~~;""<~~~;-~•.~·: ' .

CH .. . ·:.1_. i CH3 - ... ,., . -~ .., CH3 - - •. , .
• ·t .

(tat-butyl..!...-) • ,•• (2-Methylprop,l-ene)

rr: •; i { ,.:1 ----- ..
..

Xamldea
_ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ ___;__Alcohols, Phenols and Ethers 1441

Q. 43. How may the foDowing conversions be carried out:

.
.'
(i) Propene to propan-2-ol . ..
. ..
,

(ii') Anisole to phenol (Write the reaction only) ,

.r,. •

Ans. (1) CH3 - CH2 + H _.OS03 H (cone.) --+ CH3 -CH-CH3

Propcrie -----------Sulphuric acid . I
OS03H
lsopropyl hydrogen sulphate

ff 30, A 1- H 2 SO,
.. \
H1(
CH3 -1"~: ~3 I)
OH
Propan - 2 - ol
. ., .
1~ .
i; ..
H .
,,.__ '
"•
3
u ..,;• f :.,' 't• .. . : -·
Q ·;!
..
c· - • - 1" • - (' ' , '! -
~-1. -, "·•. , . -!' ,

373K
(i1) ; ; + HI
Anisolc Phenol ...... ' -
I".. >. ,
Q. 44. How would you obtain ·; ..
i •; ! .:•
(,') picric acid (2, 4, 6-trinitrophenol) from phenol? .,
I

(ii') 2-Methylpropene from 2-Methylpropanol? " ' [CBSE lhlhi 2011)

1H OH f : •
·- _,_,. ,I:;t
Ans. (1) Q ., H2S04 (oonc.)., ... ¢ - 5 03H \ ,1 HN03 (00.:,./ 02

Phenol ,, • • . • .E. S03H ·, _. •

•
, •.,._ "NO2 ·•••,
;, '•.' ·
1 ... 1 .. ' ...
~. J .,, \.

.. ' Phenol-2.4 . ., ,·,,:, .:, tic· Picric acid ,; ; -:-

disulpbonic acid • ';
·:: .._,,_~ ,.i : .. ,k:I~.\~-·i.~• ._A.J ~,··L?•;~:-..:•· 1i,.
CH ... , .
CH3
(i,) CH3---tH-CH2 OH 1
,
+SOCl2 CH ---tH~Hi-Cl +KOH (ale.)
3 .J, • • •
cuS~2
2-Mcthyl propanol 2-Methyl propene
Q. 45. How would you obtain the following:
(,') Benzoquinone from phenol
.. ; :::

..:-.. ,. (ii') 2-Methylpropan-2-ol from methylmagnesium bromide

,.-·-
_)·~t;·! 4-•-Jyi. • ·,·( ..'

0
(iii') Propan-2-ol from propene . ; [CBSE (Al) 2011:1 (F) 2011)

¢
( ,,,
0
. .--:~-·~ !
Na2Cr2°'1/H2S04
. Ans. (1)
r- . . . . ,.... ' '· ~: -'::__) ':. '"'
Phenol
0 ..
Benzoquinone

0~ OMgBr OH
.. ,. ~: /,;
(i,) CH3 ~ H3 + C 3MgBr CH3--{-CH3
+H20
.. ' •cii:4---0l3
Propanone Methyl ma~ium
bromide
CH3 CH3
2-mcthyl propan-2-ol ...' .
,-.•
...

n•
(ii,) CH3 - CH= CH2 + H 2 O Markovnikov' s CH3 - · CH-- CH3
Propene addition I
OH
Propan-2-ol ' i.. ,· \

Xamld~ii
 442 \ Xam idea Chem istry- XII,_. .;..--- ------- ------- ----.

Q.46.
Dnw the structure and name the product formed if the following alcohols an oxidised•.Assume
an excea of oxidising agent Is used. • •• •
(i) Cll,CH2CH2CH2OH (ii) 2-butenol
(iii) 2-methyl-1-propanol [CBSE Delhi 2012)
Ans. (1) CH -CHr-CH2-CH2-0H --.J..01--- --. CHr--CHr- CHz-COO H
3 Cr03 -H 2SO4 •
Butan-l-01 Butanoic acid

(i1) CH3-CH=CH- CHr-0H _ _ _lOJ____. CH3--CH=CH---CHO

PCC
But-2~1 But-2-enal

C"3
I co> • I
(iii) Cff3-CH -CH2-0H ------- + CH3-CH ---COOH
Cr03 -H 2SO4
2-Methylpropan-1-0I 2-Methylpropanoic acid
Q. 47. Name the following compounds according to IUPAC system.
c11iou •
I
(i) CH3 -CH2 - y e - CH-yH-C H3
.[NCE11J
-
J

C~CI C~ ' f

CBiOH .' .
.- I
_<u) CH3 ._ ye~_CH2 .- ~H-CH--: - CH3
. C~ • OH .
•
Ans. (1) 3-Chloromethyl-2-isopropylpentan-1-ol (iz) 2, 5-Dimethylhexane-1,3-diol
Q.48. Which of the following is an appropriate set of reactants for the prepantioa ti
l-methoxy-4-nitrobenzene? (NCER1J

(,) •¢ ¢;·
Br ,
,··
.-
+ CH30Na • - : · :; I
(i,) ,,,
NO2 NO2
.
A
'
Ans. (iz)
Q. ~9. Arrange the following compounds in decreasing order 'of acidity. -· [NCERT Exe-
(1) H2O, ROH, HC== CH
. . ; l
(ii) Arrange the following in decreasing order of their acidic character:
. '.
(a) C H 3 ~ H (b) 02N-@- oH (c) C61fsOH. • · .
(iil) Arrange the following in order of decreasing acid strength: "'
CH3OH, H2O,. C,ffsOH
Ans. (1) H20 >ROH> HCe:CH (iz) (b) > (c) > (a).
(iii) C6ffsOH> H2O> CH3OH
Q. SO. Answer the following questions.
(i) Among m, HBr, HCI, m is most reactive towards alcohols. Why? .
(ii) Of the two alcohols; (a) CHr=CH-C H2OH and (b) CHz==CH- CHz-CH OH, whicb one wll
2
read more easily with cone. HCI in the presence of ZnCl2? . [CBSE (F) Z0lZ]
Ans. (1) HI has the lowest bond dissociation energy due to longer bond length that is why it is most reactive.
(ii) CHpCH-C H20H

Xamidea