2.

Write the lUPAC name of the following:

CH3
CH-C-CH-CH3
H5C, OH
(2018) Ap
compound:
3. Write the IUPAC name of thefolowing
H,C Ç=Ç-CH, OH
Br
(AI2017)
H¡C
4. Write the IUPAC name of the following
compound:
-CH=CH-CH,OH
(AI2017) (Ap
5. Write the IUPAC nameof thefollowing compound:
CHa
CH-0-C-CH,
CH3 (Al2017)
6. Write the IUPACname of the given compound.
CH2-CH,-OH
(AI2016)
7. Write the IUPACname of the givencompound:
O,N OH

NO, (Delhi 2015) Ap

8, Write the IUPAC name of the givencompound:
CH,=C-CH,-OH
(AI 2015)
CH,
24. Carry out the following conversion:
Phenol to salicylaldehyde (1/5, 2020)
25. Carry out the following conversion:
C Propene to propanol (1/5, 2020) (Cr
26. Predict the reagent for carrying out the following
conversion:
C Phenol tobenzoquinone (1/5, 2020, 2019)
27. Predict the reagent for carrying out the following
conversion:
C Phenol to 2,4,6-tribromophenol (1/5, 2020)
28. Write the preparation of phenol from cumene.
(1/3, 2020)
29. Howcan you convert the following?
c Phenol to chlorobenzene. (1/3, 2020)Cr
30. How can you convert the following?
Sodium phenoxide to o-hydroxybenzoic acid.
(1/3, 2020)
OR
Write the equation involved in the following
reaction:
Kolbe's reaction (1/2, Al2019, Delhi 2014C)
can you convert the following?
31. How (1/3,2020)
Ethanol to propanenitrile.
32. Give reason for the following:
Phenolis more acidic than ethanol.
(1/3, Al 2017C, 2015) (An)
33. Write the equation involved in the acetylation of
salicylic acid.
(Delhi2015)
34. Which ofthe following isomers ismore volatile:
o-nitrophenol or p-nitrophenol?
(Delhi 2014) An
35. Writethe equation involved in the following reaction:
Reimer -Tiemann reaction. (1/2, Al 2014)
36. Predict the products of the following reactions :
() CHCH,OH Cu/573 K
(ii) CoHOH Br2(a4) (2023)
37. For the pair phenol and cyclohexanol, answer the
following:
(a) Why is phenol more acidic than cyclohexanol?
(b) Give one chemical test to distinguish between
the two. (2023)
38. Account for the following:
(i) Phenol isa stronger acid than an alcohol.
(ii) The boiling point of alcohols decreases with
increase in branching of alkylchain.
OR
() Write the mechanism
H+
of the following reaction
CH,CH2OH 443KCH,=CH2 + H,0
(i) Write theequation involved in Reimer-Tiemann
reaction. (2023)
 when:
39. Write structures of theproducts formed
Propan-2-ol is heated with Cu at 573 K.
()
(ii) Salicylic acid is treated with (CH;CO),O/H.
(2021C)
40. Carryout the following conversions:
) Phenol to Anisole (2021C)
(ii) Aniline to Phenol
which one will
41. Out of t-butyl alcohol and n-butanol, and why?
undergo acid catalysed dehydration faster
(2/5, 2020) An
carried out?
42. How are the following conversions
) Propene to propan-2-ol
(i) Benzylchloride to benzyl alcohol
(2020C, 2/3,Delhi 2015C) (Ap
of ethanol
43. Give the mechanism for the formation
from ethene.
(2/5,2020, Al 2015)
the major product(s) of the following reactions:
44. Write
CH,-0H
Cu
1
HCI
;i) (CH),COH 573 K
()

OH (2/3, 2020)(U)
45. How do you convert the
C (a) Phenol to Toluene following?
(b) Ethanolto Ethanal
46. (a) Show the
chemical reaction with bond (2019)
movements and arrowS for the nucleophilie
attack of water on carbocation in acid
hydration of alkenes. catalysed
(b) Give IUPACname for the
following:
OH
HC CHg

47. Write the

(2019C)
structures of the main products in the
following reactions:

()
CH,-C-0CH NaBH4

(i)
CH=CH, +H,0
H*

(2/3, 2018) Ap
48. Explain the mechanism of dehydration steps of
ethanol.
Ht
CH,CH,OH-443KCH,-CH,+H,o
(2/3, 2018C, Delhi 2015C)
 49. Write the product(s) in the following
OH reactions;
COOH
(0) (CH,CO),0
>?
H*

PCC
(ii) CH3--CH=CH-CH,-OH?
(2/5, Delhi 2017)
50. Give simple chemical tests to distinguish betwen
the following pairs of compounds:
(0) Ethanol and phenol
(ii) Propanol and 2-methyipropan-2-ol.
(2/5, Delhi 2017)
51. (a) Arrange the following compounds in the
increasing order of their acid strength:
p-cresol,p-nitrophenol, phenol
(b) Write the mechanism (using curved arrow
notation) of the following reaction:
H,0*
CH,= CHyCHg- CH,+H,o (AI 2017)
52. Write the structure of the products when
butan-2-olreacts with the following:
(a) CrO3
(b) SOCl, (AI 2017)(4)
53. Write the main product(s) in each of the following
reactions:
() CH,- CH= CH, (i) BzH,
() 3H,0,/OH
() ag. NaOH (Delhi2016)
(ii) C¢H5-OH (ii) CO, H*
 AWrite the final
product(s) in each of the following
reactions:

() CH3CH,-CH -CHaCu/573KK
OH
() CHCl + aq.NaOH
(ii) C&Hs-OH (ii) H* (Delhi2016)
55. Write the mechanism of the following reaction:
HBr
CH,CH,0H-CH,CH,Br +H,0
(AI2014, 2/3, Foreign 2014)
56. Name thereagents used in the following reactions:
() Bromination of phenol to 2,4, 6-tribromophenol
(ii) Butan-2-one to Butan-2-ol
(ii) Friedel-Crafts alkylation of anisole
(iv) Oxidation ofprimary alcoholtocarboxylic acid
(Foreign 2014) Cr)
57. Name the different reagents needed to perform the
following reactions:
(i) Phenol to Benzene
(ii) Dehydration of propan-2-olto propene
(ii) Friedel-Crafts alkylation of anisole
(iv) Dehydrogenation of ethanol to ethanal
(Foreign 2014)
A0. (i) Why is the C--O bond length in phenol less than
that in methanol?
(ii) Arrange the following in order of
increasing
boiling point:
Ethoxyethane, Butanal,Butanol, n-Butane
(ii) Howcan phenol be prepared from anisole? Give
reaction.
(2023)
61. How do youconvert the following: (Any three)
C(a) Phenol to picric acid
(b) Propanone to 2-methylpropan-2-ol
(c) Phenol toanisole
(d) Propene topropan-1-ol (2023)
62. Write the product(s) of the following reactions:
OH

PCC
(0)
 OH
COOH
(i) (CH,CO),0
CH,COOH

H,0+
(ii) + CHzMgBr (2020) Ap)
63. Write the products of thefollowing reactions:
(i) CHg CH2 O-CH3+ H|’
OH

(ii) + Br2 CS2

OCH3
Anhyd. AlCl,
(ii) + CH,COCI
+ (2019)

64. Give one chemical test to distinguish between the

following:
(a) Phenol and 1-propanol
(b) Ethanol and dimethylether
(c) 1-propanol and 2-methyl-2-propanol (2019)
 65. (a) Show how will you synthesise the following
alcohol prepared by the reaction of a suitable
Grignard reagent on methanal?
CH3-ÇH-CH,-OH
CH3
(b) Writethe mechanism of the following reaction:
Ht
CH,=CH,+ H,0-CH,CH,OH (AI 2019)
66. (a) How willyou convert the following:
(i) Phenol to benzoquinone
(ii) Propanone to 2-methylpropan-2-ol
(b) Why does propanol have higher boiling point
than that of butane? (2019C)
67. Hovw do you convert the following?
C () Phenolto anisole
(ii) Propan-2-olto 2-methylpropan-2-ol
(ii) Aniline tophenol (Delhi 2015)
68. Predict the products of the following reactions:
() BzH6
(i)
CHa-CH=CH2
Brzlaq)
(i) 3H,0,/OH ’?
(i) CzH,0H- ’?
Cu/573K
(i) CHCH,OH (Foreign 2015)
69. How are the following conversions carried out?
) Benzyl chloride to benzylalcohol
(i) Ethylmagnesium chloride topropan-1-ol
(i) Propene to propan-2-ol. (AI2015C, 2014C)
70. (a) Write the mechanism of the following reaction:
HBr
CHCH,OH CHCH,Br +H,0
(b) Write the equation involved in
reaction.
Reimer-Tiemann
(Delhi 2014)
 (D

72. (a) Account for thefollowing:

(0) O-nitrophenol is more steam volatile than
p-nitrophenol.
(i) t-butyl chloride on heating with sodium
methoxide gives 2-methylpropene instead
of t-butylmethylether.
(b) Write the reaction involved in the following:
) Reimer-Tiemann reaction
(ii) Friedal-Crafts alkylation of phenol
(c) Give simple chemical test to distinguish
between ethanol and phenol. (Delhi 2019) An
73. (a) Write the formula of reagents used. in the
following reactions:
(i) Bromination of phenol to
2,4,6- tribromophenol
(ii) Hydroboration of propene and then
oxidation to propanol.
(b) Arrange the following compound groups in the
increasing order of their property indicated:
() p-nitrophenol, ethanol, phenol (acidic
character)
(i) propanol, propane,propanal (boilingpoint)
(c) Write the mechanism (using curved arrow
notation)of the following reaction:
CH,CH,0H
CHg- CH, OH,
+

CH CH -9 CH- CHg tHa0

H
(Delhi 2017) Ap
 76. Carry out the following conversion:
t-Butylchloride to t-butyl ethyl ether(1/3, 2020C
77. Predict the reagent for carrying out the followine
conversions:
Anisole to p-bromoanisole (1/3, 2020)
78. Write the equation for the preparation of 2-methy
2-methoxypropane by Williamson synthesis.
(1/3,2020)
79. Write the equations involved in the following
reaction:
Friedel-Crafts alkylation of anisole. (1/2, Al2019)
80. Write the structure of the main products in the
followingreaction:
OC,Hs
+ HI (1/3, 2018|
sollaainroction
81. Write the product in the following reaction:
CH3 HI
CH3-CH-0CH,-CH3 ’?+?
(1/5, Delhi 2017
82. Write the main product(s) in the following reaction:
CH3
CH,-C-0-CH3 + HI
CH3 (1/3, Delhi 2016, 1/2, Al2016)
83. How is the following
conversion carried out?
Anisole to p-bromoanisole (1/3, Delhi 20150)
84. Write the equation involved in the
Williamson synthesis followingreaction:
(1/2, Al 2014, Delhi 2014C, 1/3, AI 2014C)
SA I (2 marks)
85. Write the mechanism of the
Ht following reaction:
2CH,CH,OH 413 K >CHCH,OCH,CHg +H,0
(2/3, 2020, 2/3, AI2017, Delhi 2016, 2015)
86. Predict the major product
obtained when t-buty
 bromide reacts with sodium methoxide. Als0, give its (ii) Illustrate hydroboration
IUPAC name. Oxidation reaction
(2019C)
87. Give reasons for the following: with an example. (2023)
() Boiling point of ethanol is higher in comparison 89. Give the structures of final products expected from
to methoxymethane. the following reactions:
() (CH3),C-0-CH on reaction with HI gives
(6) Hydroboration of propene followed by oxidation
CH,OHand (CH),C-las the main products and
not (CH3),C-OH and CHl. (2/3, Al2015) An) with H,O, in alkaline medium.
SA I| (3 marks) (ii) Dehydration of (CH);C-OH by heating it with
88. () Give mechanism of the following reaction 20% H;PO, at 358 K.
H,SO4
CH,CH,OH 413 K () Heating(CH,
of -owith H.
CH,CH,-0-CH,CH3 + H,0
(2020) (An