SHASHIKANT

1 Mark Questions
Multiple Choice Questions
1. Which of the following observation is shown by
7. During dehydration of alcohols to alkenes by heating
with concentrated H₂SO4, the initiation step is
2-phenyl ethanol with Lucas reagent? CBSE SQP 2024
(a) protonation of alcohol molecule CBSE 2021-22 (Term-1)
(a) Turbidity will be observed within five minutes.
(b) formation of carbocation
(b) No turbidity will be observed. (c) elimination of water
(c) Turbidity will be observed immediately.
(d) formation of an ester
(d) Turbidity will be observed at room temperature but
will disappear after five minutes. 8. A compond (X) with the molecular formula C,H,O
2. The product formed in the reaction can be oxidised to another compound (Y), whose
molecular formula is C,H,O₂. The compound (X) may
O
COOC Hs NaBH₂
be
CBSE 2021-22 (Term-1)

CBSE 2023 (a) CH₂CH₂-0 CH,

HO. COOC₂Hs (b) CH₂ CH_CH,
CH2OH
(a) (b)
OH
(c) CH, CHA CH₂ OH
HO. CH₂OH COOC HỌ (d) CH, CH,— CHO
(d)
9. Which of the following reagents will not convert ethyl
alcohol into ethyl chloride?
CBSE 2021-22 (Term-1)
(a) PCI, (b) NaCl
3. Which of the following alkenes on acid catalysed
hydration gives a tertiary alcohol? CBSE 2023 (c) SOCI, (d) HCI/ZnCl₂
(b) 2-methylpropehe 10.
(a) 2- butene O
COOCH, HO
COOCH,
(c) Propene (d) 1- butene

4. Which of the following alcohols will not undergo

oxidation ? CBSE 2023 Which of the following reagents should be used to
carry out the above conversion?
(a) Butanol
CBSE 2021-22 (Term-1)
(a) LIAIH (b) NaBH,
(b) Butan-2-ol
(c) Zn-Hg/HCI (d) KMnO4
(c) 2-methylbutan - 2- ol
11. Phenol on being heated with concentrated H₂SO, and
(d) 3-methylbutan - 2- ol then with concentrated HNO, gives
5. For conversion of propene into 1- propanol, which of CBSE 2021-22 (Term-1)
the following reagents and conditions should be used ? (a) o-nitrophenol (b) 2, 4, 6-trinitrophenol
(a) Conc. H₂SO4 H₂O and heat CBSE 2023
(c) p-nitrophenol (d) m-nitrophenol
(b) B₂H: H₂O₂/OH 12. Lucas reagent produces cloudiness immediately with
CBSE 2021-22 (Term-1)
(c) Dilute H₂SO4
CH,
(d) H₂O/H
(a) CH₂-C-CH, (b) CH₂-CH-CH₂-CH,
6. The major product of acid catalysed dehydration of
CBSE SQP 2023
1-methylcyclohexanol is OH OH

(a) 1-methylcyclohexane
(c) CH₂-CH₂-CH₂-OH
(b) 1-methylcyclohexene
(d) CH₂-CH-CH₂-OH
(c) 1-cyclohexylmethanol L
(d) 1-methylenecyclohexane CH,
 [Link]'Othe
13. Phenol does not undergo nucleophilic substitution 18. Assertion (A) Alcohols react both as nucleophiles and
reaction easily due to CBSE SQP 2021-22 (Term-1) electrophiles.

(a) acidic nature of phenol Reason (R) The bond between C- O is broken when
alcohols react as nucleophiles. CBSE SQP 2024
(b) partial double bond character of C-OH bond
(c) partial double bond character of C-C bond 19. Assertion (A) C₂H,OH is a weaker base than phenol
(d) instability of phenoxide ion but is a stronger nucleophile than [Link] SQP 2020
14. Identify the secondary alcohols from the following set Reason (R) In phenol, the lone pair of electrons on
CBSE 2021-22 (Term-1) oxygen is withdrawn towards the ring due to
(1) CH₂CH₂CH(OH)CH, (ii) (C₂H5), COH resonance.

OH Very Short Questions

LOH

(iv) CH3
20. In the process of wine making, ripened grapes are
crushed so that sugar and enzymes should come in
contact with each other and fermentation should start.
(a) (i) and (iv) What will happen if anaerobic conditions are not
(b) (i) and (iii) maintained during this process? CBSE SQP 2018

(c) (i) and (ii)

21. Write the IUPAC name of the following.
(d) (i), (iii) and (iv)
CH3
15. The boiling points of alcohols are higher than those of 1
hydrocarbons of comparable masses due to
(a) hydrogen bonding CBSE SQP 2021-22 (Term-1)
CH₂-C-CH -CH₂

(b) ion-dipole interaction H,C₂ OH CBSE 2018

(c) dipole- dipole interaction

22. Write the IUPAC name of the following compound.
(d) van der Waals' forces

16. What would be the reactant and reagent used to obtain

H₂C
C-C-CH₂-OH All India 2017

2,4-dimethylpentan-3-ol? CBSE SQP 2021-22 (Term-1) CH, Br

(a) Propanal and propyl magnesium bromide
23. Write IUPAC name of the given compound.
(b) 3-methylbutanal and 2-methyl magnesium iodide
CH₂ CH₂OH
(c) 2-dimethylpropanone and methyl magnesium iodide
(d) 2-methylpropanal and iso-propyl magnesium iodide All India 2016

17. Lower molecular mass alcohols are

24. Write the IUPAC name of the given compound.
CBSE SQP 2021-22 (Term-1)
O₂N. OH
(a) miscible in limited amount of water
(b) miscible in excess of water
NO₂ Delhi 2015
(c) miscible in water in all proportions
(d) immiscible in water 25. Write the IUPAC name of the given compound:
Assertion-Reason -CH,
HO—CH,—CH=C–CH,
■ Directions (Q. Nos. 18 and 19) In the following
CH, Foreign 2015
questions an Assertion (A) is followed by a
corresponding Reason (R). Use the following keys to 26. Which of the following isomers is more volatile :
choose the appropriate answer. o-nitrophenol or p-nitrophenol? All India 2014

(a) Both (A) and (R) are correct and (R) is the correct 27. Name the alcohol that is used to make the following
explanation of (A). ester.

(b) Both (A) and (R) are correct but (R) is not the correct
explanation of (A). CH3 -C-0-CH-CH,
(c) (A) is correct and (R) is incorrect.
(d) (A) is incorrect and (R) is correct. CH, All India 2014C
 Write IUPAC name of the following compound. Or Explain the mechanism of dehydration steps of
–CH–CH,—OH Foreign 2014
ethanol. CH₂CH₂OH
H*
CH, CH, * HẠO
OH
443 K
Delhi 2015C, All India 2013
biles 29. Of the two hydroxy organic compounds ROH and
R'OH, the first one is basic and other is acidic in 2 Marks Questions
a
behaviour. How is R different from R
KEY IDEA
Delhi 2013C
43. For the pair phenol and cyclohexanol, answer the
CBSE 2023, SQP 2023
following.
+1-effect of alkyl group increases the basic character of
alcohols and --effect of alkyl group increases the acidic
(1) Why is phenol more acidic than cyclohexanol ?
character of alcohols. (ii) Give one chemical test of distinguish between the
two.

30. How is toluene obtained from phenol? Delhi 2013C 44. Given the structures and IUPAC name of the products
CBSE 2023
31. o-nitrophenol has lower boiling point than expected from the following reactions.
p-nitrophenol. Explain. Delhi 2013C

(1) Reaction of methanal with -MgBr

32. How would you obtain ethane -1, 2-diol from ethanol?
All India 2013 C
following by hydrolysis.
33. Draw the structure of hex-1-en-3-ol compound. (ii) Reaction of phenol with Br₂ (aq).
Delhi 2012
45. Write the mechanism of the following S 1 reaction,
34. Draw the structural formula of 2-methylpropan-2-ol
molecule Delhi 2012
(CH₂),C-Br
Aq. NaOH
→(CH,),C—OH+NaBr
35. Write the IUPAC name of the following compound. All India 2020

Foreign 2012
46. Write the mechanism of acid dehydration of ethanol to
CH3-CH=CH-CH-CH₂-CH, yield ethane. CBSE SQP 2019

OH 47. (1) Arrange the following compounds in the

36. The C- O bond is much shorter in phenol than in increasing order of their acidic strength.
ethanol. Give reason Delhi 2012C p-cresol, p-nitrophenol, phenol

37. How could you convert ethanol to ethene? All India 2011
(ii) Write the mechanism (using curved arrow
notation) of the following reaction.
38. Write the equations involved in the following reaction. H₂O*
Reimer-Tiemann reaction All India 2012
CH₂=CH₂ CH, CH₂ + H₂O
All India 2017
Or Write Reimer-Tiemann reaction by giving an example.
All India 2011
48 How are the following conversions carried out?
(i) Propene to propan-2-ol
39. Draw the structure of 2,6-dimethylphenol. All India 2011 (ii) Ethyl chloride to ethanal Delhi 2014 C
40. Write the chemical equation for the preparation of
phenol from benzene using oleum and sodium 49. Write the mechanism of the following reaction.
HBr
hydroxide. Delhi 2011
CH₂CH₂OH- → CH₂CH₂Br + H₂O
41. Write the structure of the molecule of compound whose Foreign 2014; Delhi 2014
IUPAC name is 1-phenylpropan-2-ol. All India 2010 50. How will you convert the following?
42. Write the mechanism of acid dehydration of ethanol to (i) Propan-2-ol to propanone
yield ethene.
All India 2015C (ii) Phenol to 2,4,6-tribromophenol Delhi 2013
KEY IDEA 51. How will you convert
Steps involved in acid catalysed dehydration of alcohol are (i) propene to propan-1-ol?
(1) Protonation of alcohol (ii) ethanal to propan-2-ol? Delhi 2013
(ii) Formation of carbocation
52. How will you convert
(iii) Elimination of proton
(i) propene to propan-2-ol?
(ii) phenol to 2,4,6- trinitrophenol? Delhi 2013

u shol
 (ii) Write the equation of the reaction for the
53. Explain the mechanism of acid catalysed hydration of preparation of phenol from cumene.
an alkene to form corresponding alcohol. All India 2012
63. Write the product(s) of the following reactions.
54. Explain the following behaviours. OH

(1) Alcohols are more soluble in water than the COOH

hydrocarbons of comparable molecular masses. PCC (11)

(CH₂COO

(ii) Ortho-nitrophenol is more acidic than 0 CH₂COOH

All India 2012

ortho-methoxyphenol.

KEY IDEA
(0) Consider polar nature of water as well as alcohol, +CH,MgBr H,0
(iii) All India 2020
presence of H-bonding
(ii) Acidity is the tendency to give a proton. It depends
upon the stability of phenoxide ion formed (in case
of phenols). Higher the stability of phenoxide ion,
64. Give the structures of final products expected from the
following reactions.
more will be the acidic character. followed by oxidation
(1) Hydroboration of propene
55. How would you obtain Delhi 2011 with H₂O₂in alkaline medium.
OH by heating it with
(i) picric acid from phenol?
(ii) 2-methyl propanol from 2-methylpropene?
(ii) Dehydration
20% H, PO,
of-
at
(CH₂),C
358
K.
56. Account for the following. (iii) Heating of -CHo
(i) Propanol has higher boiling point than butane. Delhi 2020
(ii) Ortho-nitrophenol is more acidic than with HI
Delhi 2011C
ortho-methoxy phenol. 65. How can you convert the following?
57. Account for the following. (1) Phenol to o-hydroxybenzaldehyde
(1) The boiling points of alcohols decrease with (ii) Methanal to ethanol
Delhi 2020
increase in branching of the alkyl chain. (iii) Phenol to phenyl ethanoate
(ii) Phenol does not give protonation reaction readily.
Delhi 2011C 86. (i) How will you synthesise the following alcohol
from appropriate alkene?
58. How are the following conversions carried out?
(i) Benzyl chloride to benzyl alcohol
(ii) Methyl magnesium bromide to
Delhi 2010
2-methylpropan-2-ol OH

59. How are the following conversions carried out? (ii) Write the mechanism of the following reaction.
(i) Propene to propan-2-ol
CH₂CH₂OH →CH,=CH, * HẠO
(ii) Ethyl magnesium chloride to propan-1-ol Delhi 2010 All India 2019

60. Write the mechanism of hydration of etheneForeign

to
ethanol.
2010 67. An alcohol A (C₂H₂O) on oxidation with acidified
61. Give one chemical test to distinguish between the potassium dichromate gives acid B (C₂H₂O₂)
following pairs of compounds. Compound 4 when dehydrated with conc. H₂SO, at
443 K gives compound C. Treatment of C with
(1) Phenol and benzoic acid Delhi 2010C aqueous H₂SO4 gives compound D (C₂H₂O) which is
(ii) 1-propanol and propan-2-ol an isomer of A.

3 Marks Questions Compound D is resistant to oxidation but

compound 4 can be easily oxidised.
62. (1) Write the mechanism of the following reaction : CBSE 2023
Identify A, B, C and D. Name the type ofCBSE
isomerism
SQP 2019
H exhibited by A and D.
CH₂-CH₂-OH →CH,=CH,*HẠO +

443K