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Alcohols, Phenols and Ethers
Alcohols, Phenols and Ethers
OH
CH3
CH 3
CH3 CH CH CH CH 2OH
(a)
Cl
CH 3 CH 3
(b)
CH 2 OH
(c)
CH3 CH2 CH CH CH CH 3
CH3
CH2 Cl
CH2 OH
CH3 CH CH 2 CH CH CH 3
(d)
CH 3
OH
OH
H 3C CH CH CH 2 CH 2 CH3
OH
(f)
Br
(e)
CH 3 C C CH2 OH
(g)
Q3.
CH 3 Br
CH 3 CH CH 2 CH CH CH 2CH 3
(a)
OH
OH
C2 H 5
(b)
CH 3 CH CH CH 3
OH OH
CH3
CH3 CH CH C CH3
OH
CH3
(d)
CH 3 OH
CH 3CH CHCH 2 OH
(e)
OH OH
(f)
C6 H 5CH 2OH
CH3
OH
CH3 CH 2 CH 2 CCH 2CH 3
CH2 Cl
(g)
Q4.
Q5.
CH 3CH 2 CHCH 2 OH
C6 H 5
(h)
names.
Q6.
Q7.
Q8.
(ii) 2-Phenylpropan-2-ol
(iii) 4-Methylcyclohexen-2-ol
(v) 4, 6-Dimenthylheptan-2-ol
(vi) But-3-en-1-ol
(vii) 2-Ethyl-but-2-en-1-ol
(viii) 3-Cyclohexen-1-ol
Write structure of the compounds whose IPAC names are given below:
(a) 2-Methylbutan-2-ol
(c) 3,5-Dimethylhexane-1,3,5-triol
Give structures of all the cyclic isomers (alcohols) with molecular formula
C4 H 7 OH . Write
Give the structures and IUPAC names of products expected from the following reactions:
(a) Catalytic reduction of butanol
(b) Hydration of propene in the presence of dilute sulphuric acid.
(c) Reaction of propanone with methyl magnesium bromide followed by hydrolysis.
CH2 OH
Q12. Use a Grignards reagent to prepare the following alcohols:
(a) 2-Phenyl butan-2-ol
Q16. Write the structures of the major products expected from the following reactions:
(i) Mononitration of 3-methyl phenol
(iii) Mononitration of phenylethanoate
Q17. Complete the following reactions:
CHO
(a)
(i) NaBH 4
(ii) H 3O
MgBr
CH 3CHCH 2 CHO +
(i) Ether
(ii) H , H 2O
CH 3
(b)
CH2
O
?
(i) Hg (OAc) 2 , H 2O
(ii) NaBH 4 , NaOH
[O]
(c)
(e)
(d)
CH3CH 2CH 2C CH
H 2O , H
Hg 2
NaBH 4
CH = CHCHO
H , H 2O
(i)
O3 , Zn, H 2O
CH 3 CH2 CH CH = CH2
(iii)
BH3 , THF
H 2O , OH
C2 H 5
CH2
(iv)
B + C
LiAlH 4
(ii)
CH CH 3
OH
H
170C
CH 3CH 2MgBr ,
ether
H 3O
(v)
Q19. Give the equation for the following reactions:
(a) Reaction of bromine in
(b) Reaction of dil.
CS 2 with phenol
(c) Treating phenol with chloroform in the presence of aqueous KOH at 343 K.
Q20. Identify A to E in the following:
CH 3 CH 2 CHCH 3
OH
Cu ,250C
(i)C2 H 5MgBr
(ii ) H 3O
PBr3
Mg , ether
C2 H5 CHO
H 3O
C6 H 5 N 2Cl
H 2O , H
Boil
(ii)
C2 H 5OH
Cu ,573 K
X
X
( CH 3CO )2 O
CH 3 MgBr
H 2O / H
Y+
CH 3COOH
Q23. Give the structural formulae and IUPAC names of the isomers with the molecular formula
Q25. Arrange the following in order of increasing reactivity towards Lucas reagent:
Butan-1-ol, 2-methylpropan-2-ol, butan-2-ol.
H 2 SO4 at 443 K?
Q27. What products are obtained when ethyl alcohol is treated with
at (iii) 383K?
Q28. What happens when tert. butyl alcohol is treated with reduced copper at 573K?
Q29. Complete the following:
(a)
CH 3COCl C2 H 5OH
Pyridine
(b)
(CH 3 ) 2 CO CH
3 MgBr
(c)
(CH 3 ) 2 CO
LiAlH 4
(d)
H , H 2O
H 2O, CH 3OH ,
(CH 3 ) 2 CHOH .
Q31. What is the main product formed when phenol is subjected to Kolbes reaction?
Q32. Arrange the following in the increasing order of acidic strength : phenol, ethanol,
o-nitrophenol
Q33. What happens when phenol is hdrogenated?
Q34. Two isomeric aromatic compounds A and B have the molecular formula
purple colour with
C7 H 7OH . A gives
C6 H 6
Cl2
AlCl2
2 , HCl
NaNO
C H NH 2
273 K
(b) 6 5
aq . NaOH
575 K ,300 atm
H , H 2O
Warm
Y
Y
H , H 2O
Zn
Heat
Z
Z
CH 3
CH 2 CH 2C = CH2
(i) BH3
(ii) NaOH ,H 2O2
Q39. Arrange the following compounds in increasing order of their acid strength:
Propan-1-ol, 2, 4, 6-trinitrophenol, nitrophenol, 3, 5-dinitrophenol, phenol, 4-methyl
phenol.
Q40. Can we dry ethanol by anhydrous
CaCl2 ?
(ii) 2-Methylbutan-2-ol
(iii) 3-Methylbutan-2-ol
Q46. Propose a convenient method for preparing tert-amyl alcohol using a Grignard reagent.
Q47. What is Jones reagent? Give the product of oxidation of
H
(i)
(ii)
CH2 OH
OH
OH
OH
OCH3
NO2
C2 H 6 Br
aq . KOH
Cu
573 K
Y+
H2
(ii)
C6 H 5 SO3 Na
NaOH
Fuse
CO2 ,410 K
4 7 atm
OH
(i)
OH
and
CH2 OH
CH 3 CH CH 3
OH
(ii)
and
Q65. Write the IUPAC names of the following ethers whose common names are given:
(i) Isopropyl methyl ether (ii) Phenetole
(iv) Phenetole
Q67. Write equations for the preparation of the following ethers by Williamsons synthesis.
(a) Ethoxy benzene
(b) 1-Methoxyethane
(c) 2-Methyl-2-methoxypropane
(d) 1-Propoxypropane
(a)
C6 H 5ONa C2 H 5Cl
(b)
C2 H 5OH CH 2 N
2
(c)
(d)
C2 H 5 Br (CH 3 )3 CO Na
HBF4
Q71. Give the major products that are formed by heating each of the following ethers with HI.
CH2 O
OH
(a)
(c)
(b)
CH 3
CH 3CH 2CH 2O C CH 2CH 3
CH 3
(d)
CH 3 CH 2 CH CH 2O CH 2CH 3
CH3
OCH 2CH 3
CH 3CHCOOH
Q72. The following in not an appropriate reaction for the preparation of t-butyl ether:
C 2 H5ONa
CH 3
CH3 C Cl
CH 3
CH3
CH3 C OC2 H5
CH3
CH2
is treated with HI ?
Q80. Explain why cleavage of phenyl alkyl ethers with HBr always produces phenol and alkyl
bromide and bromobenzene and alkanols.
Q81. Ethers possess a dipole moment even if the alkyl radicals in the molecule are identical.
Explain.
Q82. Why a non-symmetrical ether is not prepared by heating a mixture of ROH and ROH in
acid?
Q83. How is 1-propoxypropane synthesized from propan-1-ol?
Q84. How does anisole react with
Br2 in CS2 ?
Q85. How do you account for the miscibility of ethoxyethane with water?
Q86. Classify the following as primary, secondary and tertiary alcohols:
CH3
CH3 C CH2 OH
(i)
CH3
(ii)
H 2C CH CH 2OH
(iii)
CH 3 CH 3 CH 3 OH
OH
CH CH 3
CH2 CH
CH3
OH
(iv)
(v)
CH3
CH = CH
C OH
CH3
(vi)
Q87. Identify allylic alcohols in the above examples.
Q88. Show how are the following alcohols prepared by the reaction of a suitable Grignard
reagent on methanal?
CH2 OH
CH3 C
(i)
CH2 OH
CH 3
(ii)
OCH 3
CH 3 CH CH
3
(i)
H 2O / H
NaBH4
(ii)
CH 3 CH 2 CH CHO
NaBH 4
CH3
(iii)
Q90. Give structures of the products you would expect when each of the following alcohol
reacts with
(a)
(i) Butan-1-ol
(ii) 2-Methylbutane-2-ol
Q91. Predict the major product of acid catalysed dehydration of (i) 1-methyl cyclohexanol and
(ii) butan-1-ol
Q92. Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures
of the corresponding phenoxide ions.
Q93. Write the equations involved in the following reactions:
(i) Reimer Tiemann reaction
Q94. What is the major product when 2-butanol is treated with conc.
Q95. How will you prepare phenol from benzene?
Q96. What happens when phenol is heated with conc.
Q97. How is cumene prepared from benzene?
HNO3 ?
H 2 SO4 at 443K?
Q98. What is the order of reactivity of 1 , 2 and 3 alcohols with sodium metal?
Q99. How will you prepare salicyclic acid from phenol?
Q100. Why cant reactified spirit be converted into absolute alcohol by simple distillation?
Q101. Name the main product obtained when vapour of tert-butyl alcohol are passed over heated
copper at 573K.
Q102. How will you prepare tert-butyl alcohol from acetic acid?
Q103. How will you convert phenol to acetophenone?
Q104. Which of the two; phenol or o-nitrophenol more acidic and why?
Q105. How will you prepare aspirin from phenol?
Q106. Phenol is heated with
CHCl3 and NaOH at 350K. what is the product formed? Give the
CO2 at 400K
Q116. How do primary, secondary and tertiary alcohols differ in terms of heir oxidation and
dehydrogenation reactions?
Q117. Write short notes on:
(i) Kolbes reaction
Q118. Write equation for the reactions which takes place when 1-propanol is treated with
(i)
SOCl2
H 2 SO4
(ii) 413K
Why is the boiling point of ether lower than the isomeric alcohol?
Q123. (a) Convert acetone to tertiary butyl alcohol.
(b) What happens when glycerol is treated with fentons reagent?
Q124. Write reactions and conditions for the following conversions:
(i) Phenol into salicyclic acid
Q125. What happens when ethanol is heated with concentrated sulphuric acid at 453 K? explain
the mechanism of this reaction.
Q126. Write the reactions with conditions for the following conversions.
(i) Methanol to propan-1-ol
H 2 SO4
(ii) conc.
H 2 SO4 at 443K
HNO3 at 5C
(b)
AlCl3 as a catalyst
KMnO4
C2 H 5OH
Na
(ii)
CH 2 CH 2
(iii)
C6 H 5OH
X
HOCl
NaOH
X
X
C2 H 5 I
Heat
H 2 SO4
413 K
Y
Y
( CH 3CH 2 )2 SO4
Cl2 , hv
alc . KOH
Heat
HNO3
Z
Z
CH 3 MgBr followed by
hydrolysis gives (C). Identify A, B and C and give the sequence of reactions.
Q142. A compound (A) reats with thionyl chloride to give compound (B). (B) reacts with
magnesium to form a Grignard reagent which is treated with acetone and the product is
hydrolysed to give 2-methyl-2-butanol. What are (A) and (B) compounds?
C4 H10O is found to be soluble in sulphuric acid. (A) does not react with
sodium metal or potassium permanganate. When (A) is heated with excess of HI, it is
converted into a single alkyl halide. What is the structural formula of (A)?
Q144. When phenol is reacted with
obtained. Which of the following species are involved in the above mentioned reaction as
intermediates?
Q145. 3, 3-Dimethyl butan-2-ol loses a molecule of water in the presence of concentrated
sulphuric acid to give tetra methylethylene as a major product. Suggest a suitable
mechanism.
Q146. Does diethyl ether