Q1.

Draw the structures of all isomeric alcohols of molecular formula

C5 H12O and give their

IUPAC names. Classify them as primary, secondary and tertiary alcohols.

Q2.

Name the following compounds according to IUPAC system:

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

Give IUPAC names of the following compounds:

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

CH3 CHCH 2CHCH 2CH 2CH 2CH 3

(c)

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)

Write the formula of the following alcohols and classify them as 1 , 2 or 3 :

(a) neo-pentyl alcohol

(b) sec-butyl alcohol(c) benzyl alcohol

(d) iso-butyl alcohol

(e) tert-butyl alcohol

(f) iso-amyl alcohol

Write all the isomeric alcohols with molecular formula

C4 H10O and give their IUPAC

names.
Q6.

Q7.

Q8.

Write the structural formulae of the following compounds:

(i) 2, 2, 4-Trimethylhexan-3-ol

(ii) 2-Phenylpropan-2-ol

(iii) 4-Methylcyclohexen-2-ol

(iv) 3-Ethyl-2, 5-dimethylhexan-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

(b) 1-Phenyl propan-2-ol

(c) 3,5-Dimethylhexane-1,3,5-triol

(d) Cyclohexyl lmethanol

Give structures of all the cyclic isomers (alcohols) with molecular formula

C4 H 7 OH . Write

their IUPAC names.

Q9.

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.

Q10. Write equations for the preparation of propan-2-ol from

(i) an alkene and

(ii) a Grignard reagent.

Q11. Write three compounds which may be used to prepare:

CH2 OH
Q12. Use a Grignards reagent to prepare the following alcohols:
(a) 2-Phenyl butan-2-ol

(b) 3-Methyl pentan-3-ol

(c) 2-Methyl pentan-2-ol

(d) 2-Phenyl propan-2-ol

(e) 3-Methyl-1-phenyl butan-1-ol.

Q13. Arrange the following sets of compounds in order of their increasing boiling points:
(a) Pentane-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol.
(b) Pentan-1-ol, n-butane, pentanal, ethaxy ethane.
Q14. Name the reagents used in the following reactions:
(a) dehydration of propan-2-ol to propene
(b) oxidation of primary alcohol to carbozylic acid
(c) oxidation of primary alcohol to an aldehyde
(d) butan-2-one to butan-2-ol
(e) cyclohexanone to 1-ethylcyclohexanol
Q15. How will you convert:
(i) Phenol to benzoic acid

(ii) Phenol to aspirin

(iii) Benzene to phenol

(iv) 1-propanol to 2-propanol

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:

(ii) Dinitration of 3-methyl phenol

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

Q18. Identify the end products A to F in the following:

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

HNO3 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

Q21. Identify the compounds X and Y in each of the following reactions;

(i)

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

Q22. Write the reactions and conditions involved in the conversion of

(a) Propene to 1-propanol

(b) Phenol to salicylic acid

Q23. Give the structural formulae and IUPAC names of the isomers with the molecular formula

C3 H 8O . Arrange them in increasing order of their boiling point.

Q24. Which structural isomer of

C4 H10O cannot be dehydrogenated by copper at 575K?

Q25. Arrange the following in order of increasing reactivity towards Lucas reagent:
Butan-1-ol, 2-methylpropan-2-ol, butan-2-ol.

Q26. What is the major product when butan-2-ol is heated with

H 2 SO4 at 443 K?

Q27. What products are obtained when ethyl alcohol is treated with

H 2 SO4 at (i) 443K (ii) 413K

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)

CH 3CH 2OH SOCl2

H , H 2O

Q30. Arrange the following in the decreasing order of acidic strength:

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

FeCl3 solution while B does not. What are A and B?

Q35. Identify X, Y and Z in the following reactions:

(a)

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

Q36. Give a method of converting benzene to phenol via nitrobenzene.

Q37. Predict which is stronger acid in each of the following pairs:
(a) Phenol or cyclohexanol
(c) p-Nitrophenol or p-chlorophenol

(b) Phenol or p-nitrophenol

(d) 2, 4, 6-Trinitrophenol or 2, 4-dinitrophenol (e) p-Cyanophenol or phenol

(f)

(CH 3 ) 2 CHOH or (CF3 ) 2 CHOH

(g) phenol or benzyl alcohol

Q38. Predict the product of the following reaction:

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 ?

Q41. How will you distinguish between 1-phenylethanol and 2-phenylethanol?

Q42. Sodium metal can be used for drying diethyl ether and benzene and not ethanol.
Q43. Arrange the following in the decreasing order of their boiling points:

CH 3CH 2OH , HOCH 2CH 2OH , CH 3CH 2Cl

Q44. Explain why alcohols are comparatively more soluble in water than the corresponding
hydrocarbon.
Q45. Arrange the following compounds in the decreasing order of their boiling points.
(i) Pentan-1-ol

(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

CH 3CH CHCH (OH )CH 3 by Jones reagent

Q48. Why has phenol higher boiling point than toluene?

Q49. Out of phenol and benzene, which is more easily nitrated and why?
Q50. Why phenol has smaller dipole moment than methanol?
Q51. Account for : unlike phenol, alcohols are easily protonated.
Q52. Arrange the following phenolic compounds in decreasing order of their acidic character:

OH

OH

OH

OCH3

NO2

Q53. Why is the boiling point of glycol high?

Q54. How do you account for the fact that unlike phenol, 2,4-dinitrophenol and 2, 4, 6trinitrophenol are soluble in aqueous sodium carbonate solution?
Q55. Boiling point of glycol is high. Why?
Q56. Why do alcohols have higher boiling points than haloalkanes of the same molecular mass?
Q57. You are given benzene; conc.

H 2 SO4 and NaOH. Write the equations for the preparations

of phenol using these reagents.

Q58. While separating a mixture of ortho and para nitrophenols by steam distillation, name the
isomer which is more volatile. Give reason.
Q59. Explain why ortho nitrophenol is more acidic than ortho methoxy phenol.
Q60. Write reaction for the preparation of phenol from cumene.
Q61. How will you distinguish between 1-phenyl ethanol and 2-phenyl ethanol?
Q62. Identify the compound X and Y in the following reactions:
(i)

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

Q63. How will you convert propan-1-ol to propan-2-ol?

Q64. Give a chemical test to distinguish between the following pairs of compounds:

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

(iii) -chloro ethyl methyl ether

(iv) Cyclohexyl n-propyl ether

Q66. Write the structural formula of the following:
(i) Di-isopropyl ether

(ii) Divinyl ether

(iii) Bis (2-methoxyethyl) ether

(iv) Phenetole

(v) p-Nitrophentole (vi) tert-Butyl methyl ether

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

(e) 1-Ethoxy-2, 2-dimethylpropane

Q68. Suggest three methods for preparing di-n-propyl ether.

Q69. Suggest a methods to prepare ethyl-n-propyl ether starting from alcohol of three C-atoms
or less.
Q70. Name the major product in the following reactions:

(a)

C6 H 5ONa C2 H 5Cl

(b)

C2 H 5OH CH 2 N
2

(c)

(CH 3 )3 CBr C2 H 5ONa

(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

(i) what would be the major product of the reaction?

(ii) Write a suitable reaction for the preparation of tert-butyl ethyl ether.
Q73. Why are ethers relatively inert compounds?
Q74. Why di tert-butyl ether cannot be prepared by Williamsons synthesis?
Q75. Sodium metal can be used for drying diethyl ether but no ethanol. Why?
Q76. Name the pair of alkyl halide and alkoxide for the preparation of ethyl tert. butyl ether.
Q77. What products are obtained when

CH2
is treated with HI ?

Q78. HI is a better reagent than HBr for cleavage of ether. Explain.

Q79. The boiling points of ethers are lower than their corresponding isomeric alcohols. Explain.

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)

Q89. Write structures of the products of the following reactions:

O
CH 2 C

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)

HCl ZnCl2 , (b) HBr and (c) SOCl2

(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

(ii) Kolbes 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

name of the reaction.

Q107. Name the majot product formed when sodium phenoxide is heated with

CO2 at 400K

under 4-7 atmospheric pressure. What is the name of the reaction?

Q108. Explain why propanol higher boiling than butane.
Q109. Name the products obtained when anisole is treated with HI.
Q110. Write the functional isomer of dimethyl ether.
Q111. Why is special care taken to distil old samples of ether?
Q112. Why do alcohol have higher boiling points than haloalkanes of the same molecular mass?
Q113. How can primary. Secondary and tertiary alcohols obtained from Grignards reagent?
Q114. How will you bring about the following conversions?
(i) Benzene to phenol

(ii) Phenol to salicyclic acid

(iii) Ethanol to ethanolic acid

Q115. What are primary, secondary and tertiary alcohols? How will you distinguish them?

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

(ii) Reimer-Tiemann reaction.

Q118. Write equation for the reactions which takes place when 1-propanol is treated with
(i)

SOCl2

(ii) a small amount of conc.

H 2 SO4

(iii) excess HBr under reflux.

Q119. How will you convert?

(a) Phenol to p-hydroxyazobenzene

(b) n-Propyl alcohol to isopropyl alcohol

(c) Ethyl alcohol to methyl alcohol

Q120. What products are obtained when primary, secondary and tertiary alcohols are passed
over heated copper?
Q121. Explain the dehydration of alcohol with conc.
(i) 443K

H 2 SO4 at the following temperatures :

(ii) 413K

Q122. How can diethyl ether be prepared from

(i) ethyl iodide

(ii) ethyl alcohol ?

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

(ii) 2-Propanone into 2-methyl-2-propanol.

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

(ii) Benzyl alcohol to benzoic acid.

Q127. (a) How will you convert phenol to aspirin?

(b) Discuss the dehydrogenation of 2 alcohol.
Q128. How is phenol prepared from cumene? How does it react with
(a) nitric acid
(c) conc.

H 2 SO4

(b) sodium metal

(d)

CHCl3 in the presence of NaOH

Give its four uses.

Q129. How is ethyl alcohol prepared commercially? How does it react with
(i)

ZnCl2 and HCl

(iii) sodium metal

(ii) conc.

H 2 SO4 at 443K

(iv) hot copper ?

Give important uses of ethyl alcohol.

Q130. How will you carry out the following conversions:
(i) 1-Propanol to 1-bromopropane

(ii) 1-Chloropropene to 1-propanol

(iii) 2-Methyl-1-pentene to 2-methyl-2-pentanol

(iv) Phenol to phenylethanoate

(v) Ethene to ethanol?

Q131. (a) How would you convert (write chemical equations):

(i) Chlorobenzene to phenol

(ii) Phenol to 4-bromophenol

(iii) Phenol to 2-acetoxybenzoic acid

(b) Formation of the products obtained by the reaction of ethanol with concentrated
sulphuric acid depends upon the experimental conditions. Justify your answer.
(c) Explain the mechanism of acid catalysed dehydration of ethanol at high temperature.
Q132. Discuss the following (any three)
(a) Relative reactivity of alcohols towards Lucas reagent (with the help of equations)
(b) Glycerol is tre4ated with HI.
(c) Phenols are acidic while alcohols are not though both have OH groups.

(d) How is phenol converted into

(i) well known acid base indicator
(ii) p-bromophenol?
Q133. How is ethyl alcohol manufactured by fermentation? Give its reaction with the following:
(i) Grignard reagent

(ii) Reduced copper at 573K\

(iii) Acetyl chloride and acetic anhydride

Q134. How would you convert (Write chemical equations) :
(i) Chlorobenzene to phenol

(ii) Phenol to 4-bromophenol

(iii) Phenol to 2-acetoxy benzoic acid.

Q135. (a) Account for the following:
(i) Phenols are acidic in nature
(ii) Unlike phenols, alcohols can be easily protonated
(b) Write the reactions involved in the preparation of :
(i) 1, 2-ethanediol from ethane
(ii) Iodoform from propanol
Q136. How is phenol obtained from sodium benzene sulphonate? What happens phenol reacts
with
(a) dil.
(c)

HNO3 at 5C

(b)

C2 H 5Cl in the presence of NaOH

Cl2 in the presence of CS 2 at 0C

(d) a mixture of HCN and HCl in the presence of

AlCl3 as a catalyst

Q137. Give chemical equations for the following reactions:

(i) Oxidation of propan-1-ol with alkaline

KMnO4

(ii) reaction of propene with mercuric acetate followed by hydrolysis

(iii) Reaction of bromine in

CS2 with phenol.

(iv) Action of dil.

HNO3 with phenol.

(v) Treating phenol with

CHCl3 in presence of aqueous NaOH at 343K.

Q138. How will you convert the following?

(a) Ethyl alcohol to tert-butyl alcohol

(b) tert-butyl alcohol to iso-propyl alcohol

(c) n-Propyl alcohol to n-hexane

(d) Ethanol to propanone

(e) 2-Propanol to 1-bromopropane

(f) Ethyl alcohol to ethylene glycol

(g) Ethylene to n-propyl alcohol

(h) 1-Propanol to 1-chloro-2-propanol

(i) Ethylene to dioxane

(j) Ethyl alcohol to vinyl acetate

(k) 2-Butanol to 2-butene

(l) 2-Methyl-2-propanol to 2-methyl

propene

Q139. How will you convert?

(a) Benzene to resorcinol

(b) Chlorobenzene to benzene

(d) Phenol to benzoic acid

(e) Phenol to aspirin

(c) Benzene to phenol

Q140. Complete the following reactions:

(i)

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

Q141. A compound (A) with molecular formula

Cl2 , hv

alc . KOH
Heat

HNO3

Z
Z

C4 H10O on oxidation forms compound (B). the

compound (B) gives positive iodoform test and on reaction with

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?

Q143. Compound (A)

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

CHCl2 and NaOH followed by acidification, salicylaldehyde is

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

C2 H 5OC2 H 5 has dipole moment? Explain.

Q147. Acid-catalysed dehydration of t-butanol is faster than that of n-butanol. Explain.