Converting Anisole to Phenol
Converting Anisole to Phenol
7. ALCOHOLS, PHENOLS
EXERCISE
i)CH,MgBr p. Then P is
Case Based Questions 3
ii)H,0
Case Based Question-1
a) Phenol
Alcohols on dehydration gives alkene at 443K, b) I-methyl Cyclohexanol
follow carbocation mechanism. Excess of alcohol d) benzaldehyde
c) hexanol
at 413K on dehydration with conc. H,SO, also
follow carbocation mechanism but give diethyl 4. C-OH bond length in CH,OH longer tha
[Link] are soluble in water, Boiling point C-OH bond length in phenol
increases with increase in molar mass and decrease a) due to double bond character in CH,OH
with branching b) due to partial double bond character inCH,0H
Alcohols undergo nucleophiic substitution c) due to partial double bond character in phenal
reactions, esterification with carboxylic acids and d) single bond character in phenol
derivatives like amids, acid halides, acid anhydride
Phenol is prepared from cumene, diqazonium salts, OH
anisole, chlorobenzene, Phenol is ued to prepare
PCC ’Xwhere X is
salicyladehyde, salicyclic acid, aspirin, methyl 5.
salicylate, p-benzoquinone. Phenol undergoes
electrophilic substitution reaction at O and p position a) cyclohexanol
Ethers are functional isomers of alcohols, have low
boiling points,. Ethers are used as solvents b) cyclo hex-1-en-1-ol
unsymmetrical ethers are prepared by Williamson c) cyclo hex-2-en-1-one
synthesis. Ethers react with HI and undergo Snl d) cyclo hex-3-en-1-one
or Sn2 mechanism depending upon Case Based Question-2
stability of
carbocation formed. Aromatic ethers like anisole
undergoes electrophilic substitution at O and p
Alcohols playan important role in our daily
positions life, In medicines and organic
used as an
solvents ordinary spirt
Based on the above information, answer the antiseptic contains methanol. Ethanol 1s
following questions: present in cough syrups, tonics, wine, beer and
1 Out of ethanol, propanol, Tertiary butyl Wisky., sugar,
alcohol which also starch,cellulose are carbohydrates
and n-butanol, which will
undergoes contain large number -OH
fermentation of sugars produce the alcohols. groups.
dehydration faster
a) propanol Phenol is also an antiseptic in low
b) Tertiary butyl alcohol (0.2%) where as 2% concentra
solution of phenol is used
c) ethanol d) n-butanol disinfectant. The frangrance of rose is due to
2. In conversion of phenol to p-benzoquinone the citronellon (unstaturated alcohol) phenol used
for
suitable reagent
a) Conc. H,SO, b) PDC
preparation of many
aspirin, methyl salicylateuseful compounds
like
30. Which of the following acids reacts with acetic Statement-II : The C-OH bond angle in
anhydride to form aspirin? alcohols is slightly less than the tetrahedral
a) Benzoic acid b) Salicylic acid angle.
c) Phthalic acid d) acetic acid
37. Statement-I : Phenol is a strong acid than an
Assertion and Reason Questions alcohol.
Both (A) and (R) are true and (R) is the Statement-II : Phenol undergoes electophiic
correct explanation of (A) substitution more easily than benzene.
b) Both (A) and (R) are true and (R) is not the 38. Statement-I : Phenyl methyl either react with
correct explanation of (A) HI to give idobenzene and methyl alcohol.
c) (A) is true but (R) is false
Statement-II : The boiling points of ethers are
d) (A) is false but (R) is true
lower than isomeric alcohols.
31. Assertion (A) : The bond anglé in alcohol and
phenol is more than tetrahedral angle 39. Statement-I : Ortho nitro phenol more acidic
Reason (R) : In phenols, oxygen is attached to than phenol.
sp² hybridized carbon Statement-II : In Williamnson's synthesis
32. Assertion (A) : Phenol gives picric acid on reaction is used to ptepare only symmetric ethers.
reaction with conc. HNO, and conc H,SO4 40. Statement-I: Anisole react with nitration
Reason (R) : Picric acid reacts with NaHCO, mixture to form ortho and para nitro anisole.
to give CO,
Statement-II: Anisole involved in electrophilic
33. Assertion (A) :Phenol gives violet colour with substitution reaction.
neutral FeC, benzyl alcohol does not
Reason (R) : Ethanol gives yellow ppt with L,
and NAOH, phenol doe not
Matrix Matching Questions
34, Assertion (A) : Cumenehydroperiodie on 41. Column-1 Column-II
hydrolysis gives phenol and acetone
1) Phenol+Neutral FeCl, p) no reaction
Reason (R) : Phenol becomes pink on long
standing due to oxidation 2) Phenol + Br,(aq) ) Violetecolour
35, Assertion (A): Phenol reacts with CO, NAOH 3) Phenol+ NaHCO, )R. white ppt
at 3-7 atm, on heating and acidification gives
salicylic acid 4) picric acid + NaHC0, s) CO, gas is
evolved
Reason (R) : It is Riemer Tiemann reaction
WINNERS SERIES For CBSE XII Students 61
QUESTION BANK
42. Column-I
Column-II CHEING
OH
OH
a) catechol
OH
2 b) Resorcionol
OH
OCH3
3) c) 0-Cresol
CH,
OH
4)
d) Catechol
OC,Hs
5)
e) Aromatic ether
) Anisole
g) Ethoxy benzene
43. Column-I Column-II
2) H-C-H RMgx
H,0/H 9 phenol
3) CH, -C-CH, RMgX
H,0/H r) acetone
4)Cumene H,0/H
S) acetone
OCH4
5) +HI
t) 20 alcohol
u) idobenzene
62 &
WINNERS SERIES For CBSE
CHEMISTRY QUESTION BANK
Column-I Coiumn-II
44.
) Oxidation of 1' alcohol in aldehyde a) Cu/300°C,A
3)
( Cro,
4) 30 alcohol to alkene
c) PCC
d) Collin's reagent
5) Identification of 1°, 2° and 3° alcohols e) Lucus reagent
3) C,H,Cl+C,H,ONa r) ether
4) R-X+ Ag,0’ s) Nucelophilic substitution
t) Primary alcohols
DU. InRiemer-Tiemann reaction with CHCI, to give 45) 1-s, 2-t, 3-p, 4-r
47) NO,
Key Sheet -CH,
2) d 3) b 4) c 5) c
48) Salicyclic acid
6) a 7) b 8) c 9) d 10) b 49) True
11) d 12) b 13) d 14) d 15) c 50) False
H,C, CH,
(ii) CH, -CH, -CH -CHO- NaBH,
(i)) carboxvli
Oxidation of a primary alcohol to
acid.
(iv) OH toan
(ii) Oxidation of a alcohol
aldehyde. primary
66 Students
WINNERS SERIES For CBSE XII
CHEMISTRY QUESTION BANK
(ii) Bromination of phenol to Preparation methods of ethers
2.4,6-tribromophenol 14. The following is not an appropriate reaction for
(iv) Benzyl alcohol to benzoic acid the prepartion of t-butyl ethyl ether :
(v) Dehydration of propan-2-ol to propene CH, CH,
9. (a) Explain why ortho and para nitrophenols C,H,ONa+CH, -C-Cl ’CH, -C-0C,H,
are more acidic than phenol. [2008]
CH, CH,
(b) Draw the resonance structures of the
corresponding phenoxide ions. 15. How is 1-propoxypropane synthesised from
(c) C-0- Hbond angle in alcohols is slightly propan-1-ol? Write mechanism of this reaction.
less than the tetrahedral angle (109°28') Chemical Properties of ethers
10. Write the structures of the major products
16. Write equations for the following reactions.
expected from the following reactions: (2010]
(0) Mononitration of 3-methylphenol
(a) Fridel Crafts reaction - alkylation in anisole
(i) Dinitraion of 3-methylphenol (b) Nitration of anisole
(iü) Mononitration of phenyl methanoate
(c) Bromination of anisole in ethanoic acid
11. Write one chemical equation of eachto represent medium.
[Foreign 2007, 10, 11, 13]
(d) Fridel Crafts acetylation of anisole.
(a) Kolbe's reaction
17. How are the following conversions carried out:
(b) Williamson's synthesis Anisole to phenol. (Write the reaction only)
(c) Reimer - Tiemann reaction [2007]
(d) unsymmetrical ether
18. Give a chemical test to distinguish between the
12. How will you prepare butan-1-ol form :
following pairs of compounds.
OH OH
(i) 1-bromobutane, and
(ii) A suitable alkene ?
(i) and
13. (a) Why are phenols more acidic than (i) + CH,ONa (ii) + CH;Br
alcohols?
acid(2,4,6-trinitrophenol[)Dfrom
elhi-2phenol0|
(iii)
2-propanol to acetone (i) Picric
28. Write the major (i) 2-Methylpropane from
reactions: product(s) of the following 2-methyl propanol
9. Write the names of reagents
ÇH, -0H and
the preparation of the- equations for
i)
HCI
williamson's synthesis following ethers by
ii) (CH,), COH Cu
S73K () Ethoxy benzene
OH
(ii) 2-methoxy-2-methyI propane
29. How do you
i)
convert the. following? (ii) methoxy ehane
Phenol to anisole 10. Describe the
i) Propan-2-ol to mechanisim of alcohols reaction
2-methylpropan-2-ol
iül) Aniline to phenol both as nucleophile as well as
their reactions. electrophile in
30. Predict the products of [Foregin 2008)
the following 11. Write the product(s)
i) CH,-CH =CH, i)B, H,
reaction: in each of the following
’? reactions:
ii)3H,0, /OH [2016]
1) C,H,OH B,(anq) ’? (a) (i) CH, = CH-CH,OH PCC
) CH,CH,OH Cu/573K OH
(ii) Zn dust
ADDITIONAL QUESTIONS
Convert the following : (b) Write the
(i) 2-propanol to chloroform reaction:
mechanism of the following
(ii) Acetone to iodoform 2CH,CH,OH Conc. H,SO,/413K
2 Explain how does the OH group attached to a CH,CH,-0-CH,CH;
benzene ring activate it towards electrophilic 12. (a) Write
equations of the reactions
substitutions. (i) Bromine in CS, withfollowing
3. Why is the preparation of ether
by dehydration (1) Treating phenol with phenol
of secondary alcohol not a suitable method? chloroform in
presence of ag. NaOH
4. Convert ethanol to 1,2-ethanediol. (b) Distinguish between:
5. Write the reactions and conditions for the (i) Ethanol and
conversion of
(ii)
Diethyl ether
(i) hept -1-ene to heptanol 13.
Propanol and
t-butyl-alcohol pho_pl-
Alcohol reacts with halgoen acids orbut phenol
(ii) butan-1-o] to butanoic acid rous halides to form haloalkanes
does not form
halobenzene? Explain.
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