160 wtG CBSE Champion Chemistry Class 12

Previous Years' CBSE Board Questions

11.2 Nomenclature (c) slightly greater than 120°
(d) slightly less than 120° (Term I, 2021-22) T
VSA (1 mark) 12. Assertion (A): The C-0-H bond angle in
1 Write the lUPAC name of the following: alcohols is slightly less than the tetrahedral angle.
CH3 Reason (R) :This is due to the repulsive interaction
between the two lone electron pairs on oxygen.
CHy¢-H-CH, (a) Both Assertion (A) and Reason (R) are correct
H;Cz OH (2018) Ap) statements, and Reason (R) is the correct
explanation of the Assertion (A).
2 Write the IUPAC name of the following compound:
H,C-ç= CH,-OH (b) Both Assertion (A) and Reason (R) are correct
statements, but Reason (R) is not the correct
H, Br (AI2017) explanation of the Assertion (A).
3. Write the lUPAC name of the following compound: (c) Assertion (A) is correct, but Reason (R) is
incorrect statement.
CH=CH- CH,OH
(d) Assertion (A) is incorrect, but Reason (R) is
(AI 2017) (Ap) correct statement. (2020) Ap
4. Write the |UPAC name of the following compound:
CH, 11.4 Alcohols and Phenols

CHy-0-¢-cHs (AI2017)
MCQ
Read the passage given below and answer the following
CH3
questions (Q. No. 13 to 15):
5. Write the IUPAC name of the given compound. Alcohols and phenols are acidic in nature. Electron
-CH,-CH,OH withdrawing groups in phenol increase its acidic strength
(AI 2016) and electron donating groups decrease it. Alcohols
undergo nucleophilic substitution with hydrogen halides
6. Write the IUPAC name of thegiven compound: to give alkyl halides. On oxidation primary alcohols yield
O,N OH aldehydes with mild oxidising agents and carbOxylic acids
with strong oxidising agents while secondary alcohols
NO, (Delhi 2015) Ap yield ketones.The presence ofOH groups in phenols
Write the IUPAC name of the given compound: activates the ring towards electrophilic substitution.
7.
CH,=C-CH,-OH Various important products are obtained from phenol like
salicylaldehyde, salicylic acid, picric acid etc.
CH3 (AI2015)
13. Which of the following alcohols is resistant to
8 Write the IUPAC name of the given compound: oxidation?
OH-CH,-CH==C-CHa
CH3 (Foreign 2015) (b) CHa-CH-0H
(a) CH3-C-OH
9 Name the following according to IUPAC system :
CH,-CH-CH,-CH3 CH, CH3

OH (1/2, Delhi 2015C) (c) CH,-CH,-0H (d) CHa-OH An

10. Write IUPAC name of the following compound : 14. Which of the following group increases the acidic
HO-CH,-CH-CH, OH character of phenol?
(Foreign 2014) (a) CH0 -
OH
(c) NO (d) Allof these An
11.3 Structures of Functional Groups 15. Consider the following reaction:
OH
MCQ
() NaOH, CO, (i) CHCl,+ aq. NaOH
11. The C-O-H bond angle in alcohol is X
(i) H* (i) H*
(a) slightly greater than 109°28'
(b) slightly less than 109°28 the products X and Yare
Alcohols, Phenols and Ethers
161
OH CHO
25. Howcan you convert the following?
COOH Ethanol to propanenitrile. (1/3, 2020)
(a) X= Y=
26. Give reason for the following:
OH
OH Phenol is more acidic than ethanol.
OH
CHO
(1/3, Al 2017C, 2015) An
COOH
(b) X= Y= 27. Write the equation involved in the acetylation of
salicylic acid. (Delhi 2015)
COOH OH
28. Which of the following isomers is more volatile:
o-nitrophenol or p-nitrophenol? (Delhi 2014))An)
(c) X= Y=
OH 29. Write the equation involved in the following reaction:
Reimer -Tiemann reaction. (1/2, AI 2014, 2013)
CHO
OH OH 30. How is toluene obtained from phenol?
COOH CHO
(1/3,Delhi 2013C)
(d) X= Y= 31. Give a chemical test to distinguish between
2-pentanol and 3-pentanol. (1/2, Delhi 2013C)
(Term I, 2021-22) Of the two hydroxy organic compounds ROH and
16. In the following reaction R´OH, the first one is basic and other is acidic in
CH,-CH=CH-cH,-OH CC, behaviour. How is Rdifferent from R'? (Delhi 2013C)
the product formed is
How wouldyou obtain ethane-1, 2-diol from ethanol ?
(a) CHg-CHOand CH,CH,OHX (AI 2013C)
(b) CHg-CH=CH-COOH
(c) CH3-CH=CH-CHOv 34. How would you obtain acetophenone from phenol?
(d) CHg--CH,-CH,-CHO (AI 2013C)
(Term I, 2021-22) (U) SA I (2 marks)
17. Which of the following acids reacts with acetic 35. Out of t-butyl alcohol and n-butanol, which one will
anhydride to form aspirin?
(a) Benzoic acid
undergo acid catalysed dehydration faster and why?
(b) Salicylic acid
(c) Phthalic acid (d) Acetic acid (2/5, 2020) An)
(Term I, 2021-22) 36. Give the mechanism for the formation of ethanol
from ethene. (2/5, 2020, Al 2015)
VSA (1 mark)
37. Write the major product(s) of the following
18. Carry out the following conversion: reactions:
Phenol to salicylaldehyde (1/5, 2020)
19. Carry out the following conversion: CH,-OH
Propene to propanol (1/5, 202o) (Cr HCI Cu
20. Predict the reagent for carrying out the following A ’; (i) (CHa),COH 573 K
conversion:
Phenol to benzoquinone (1/5, 2020) OH (2/3, 2020) U)
21. Predict the reagent for carrying out the following 38. Write the structures of the main products in the
conversion:
Phenol to 2,4,6-tribromophenol (1/5, 2020) following reactions:
22. Write the preparation of phenol from cumene.
(1/3, 2020)
(i)
CH,-C-0CH3 NaBH4
23. How can you convert the following?
Phenol to chlorobenzene. (1/3,2020) (Cr) CH,=CH2 +H,o Hy
(ii
. How can you convert the following?
Sodium phenoxide to o-hydroxybenzoic acid. (2/3, 2018) (Ap)
(1/3, 2020) 39. Explain the mechanism of dehydration steps of
OR ethanol.
Write the equation involved in the following
reaction: CH,CH,OH-3CH,=CH,+H,0
Kolbe's reaction (1/2, Al2019, Delhi 2014C, 2013C) (2/3, 2018C, Delhi 2015C)
162
MtG CBSE Champion Chemistry Class 12
40. Write the product(s) in the following reactions: 50. How are the following conversions carried out?
OH
() Propene to Propan-2-ol
COOH (ii) Ethyl chloride to Ethanal
(CH,CO),0 (Delhi 2014C)
()
H* ’? 51. Explain the following with an example for each:
(0) Kolbe's reaction,
(i) CH-CH=CH-CH,-OH Pe? (ii) Reimer-Tiemann reaction (2/3, Al 2014C) R
(2/5, Delhi 2017) 52. Howwillyou convert:
41. Give simple chemical tests to distinguish between (i) Propene to propan-2-ol
the following pairs of compounds: (i) Phenol to 2,4,6-trinitrophenol? (Delhi 2013)
() Ethanol and phenol 53. How willyou convert the following:
(ii) Propanol and 2-methylpropan-2-ol. () Propan-2-olto propanone
(2/5, Delhi 2017) (ii) Phenol to 2,4,6-tribromophenol? (Delhi 2013)
42. (a) Arrange the following compounds in the 54. Explain the mechanism of the following reaction:
increasing order of their acid strength: H+
p-cresol, p-nitrophenol, phenol CH3-CH-OH a2 CH,=CH, +H,0 AI 2013)
(b) Write the mechanism (using curved arrow SA II (3 marks)
notation) of the following reaction:
H,0* 55. Write the product(s) of the following reactions:
CH,= CHy CHyCH,+H,0 (AI 2017) OH
43. Write the structure of the products when
butan-2-ol reacts with the following:
PCC
(a) CrO3 (b) sOCI, (AI 2017) Ap
44. Write the main product(s) in each of the following
OH
reactions:
(i) CH3- CH= CH, () B,H, coOH
() 3H,0,/OH (iü) (CH,CO),0,
() ag. NaOH CH,COOH
(i) CeHs-OH (i)CO,. H* (Delhi 2016)
45. Write the final product(s) in each of the following
reactions:
(0) CH,CH,-CH Cu/573 K (üi) -CH,MgBr Hy0", (2020) Ap
ÖH 56. (a) Show how will you synthesise the following
() CHCI, +aq. NaOH, alcohol prepared by the reaction of a suitable
(ii) CaHs-OH (iö) H* (Delhi 2016)
Grignard reagent on methanal?
46. How are the following conversions carried out?
) Propene to propane-2-ol
CH3 çH-CH,-OH
(ii) Benzyl chloride to benzyl alcohol CH3
(2/3, Delhi 2015C) Ap) (b) Write the mechanism of the following reaction:
47. Write the mechanism of the following reaction: CH,=CH, +H,0 ’CH,CH,OH
CH,CH,OH SCH,CH,Br +H,0 (AI 2019)
(AI 2014, 2/3, Foreign 2014) 57. Howdo you convert the following?
48. Name thereagents used in the following reactions: (i) Phenol to anisole
(i) Bromination of phenolto 2, 4,6-tribromophenol (i) Propan-2-ol to 2-methylpropan-2-ol
(ii) Butan-2-one to Butan-2-ol (ii) Aniline to phenol (Delhi 2015)
(iii) Friedel-Crafts alkylation of anisole 58. Predict the products of the following reactions:
(iv) Oxidation of primary alcohol to carboxylic acid (i) B,H,
(Foreign 2014) Cr (i) CH3CH= CH,
(i) 3H,0,/OH
49. Name the different reagents needed to perform the (i) C,H,OH-Br,laq),
following reactions:
(i) Phenol to Benzene (ii) CH,CH,OH Cu/573K (Foreign 2015)
(iü) Dehydration of propan-2-ol to propene 59. How are the following conversions carried out?
(iii) Friedel-Crafts alkylation of anisole () Benzyl chloride to benzyl alcohol
(iv) Dehydrogenation of ethanol to ethanal (ii) Ethyl magnesium chloride to propan-1-ol
(Foreign 2014) (ii) Propene to propan-2-ol. (AI2015C, 2014C)
 I

Alcohols, Phenols and Etherc

(a) Write the 163

mechanism of the following reaction:
HBr (a) Both Assertion (A) and Reason (R) are correct
CH,CH,0H- >CH,CH,Br +H,0 statements, and Reason (R) is the correct
(b) Write the equation
Tiemann reaction.
involved in Reimer explanation of the Assertion (A).
(Delhi 2014) (b) Both Assertion (A) and Reason (R) are correct
L4 (a) Give chemical tests to distinguish between the statements, but Reason (R) is not the correct
following pairs of compounds: explanation of the Assertion (A).
(i) Pentan-2-ol and Pentan-3-ol (c) Assertion (A) is correct, but Reason (R) is
(it) Methanol and Phenol incorrect statement.
(b) o-Nitrophenol is (d) Assertion (A) is incorrect, but Reason (R) is
more acidic than correct statement. (2020)
o-methoxyphenol. Explain why. (AI 2013C) An 66. Assertion (A): The C-O-C bond angle in ethers is
LA (5 marks) slightly less than tetrahedral angle.
62. (a) How do you convert the folowing: Reason (R) : Due to the repulsive interaction
(i) Phenol to anisole between the two alkyl groups in ethers.
(a) Both Assertion (A) and Reason (R) are correct
(ii)Ethanol to propan-2-ol?
(b) Write mechanism of the following statements, and Reason (R) is the correct
reaction: explanation of the Assertion (A).
CzH,OH 443
H,sO4,
K
CH,=CHz+H,0 (b) Both Assertion (A) and Reason (R) are
statements, but Reason (R) is not the
correct
correct
(c) Why phenol undergoes electrophilic explanation of the Assertion (A).
substitution (c)
more easily than benzene? (Delhi 2019) Assertion (A) is correct, but Reason (R) is wrong
63. (a) Account for the following: statement.
(i) 0-nitrophenol is more steam volatile than (d) Assertion (A) is wrong, but Reason (R) is correct
statement. (2020)Ap
p-nitrophenol.
(iü) t-butyl chloride on heating with sodium VSA (1 mark)
methoxide gives 2-methylpropene instead 67. Carry out the following conversion:
of t-butylmethylether.
(b) Write the reaction involved in the following: t-Butylchloride to t-butyl ethyl ether(1/3, 2020)(Cr
(i)Reimer-Tiemann reaction 68. Predict the reagent for carrying out the following
(i) Friedal-Crafts alkylation of phenol conversions:
(c) Give simple chemical test to distinguish Anisole to p-bromoanisole (1/3, 2020)
between ethanol and phenol. (Delhi 2019) (An 69. Write the equation for the preparation of 2-methyl
64. (a) Write the formula of reagents used in the 2-methoxypropane by Williamson synthesis.
following reactions: (1/3, 2020)
() Bromination of phenol to 70. Write the equations involved in the following
2,4,6- tritbromophenol reaction:
(ii) Hydroboration of propene and then FriedelCrafts alkylation of anisole. (1/2, AI 2019)
oxidation to propanol. 71, Write the structure of the main products in the
(b) Arrange the following compound groups in the following reaction:
Increasing order of their property indicated:
() p-nitrophenol, ethanol, phenol (acidic OC,Hs
character)
() propanol, propane, propanal (boiling point) +H| (1/3, 2018)
(c) Write the mechanism (using curved arrow 72. Write the product in the following reaction:
notation) of the following reaction:
CH,- CH, OH2 CH,CH;OH CHg--CH 0-CH,-CH,
H
’?+?
(1/5, Delhi 2017)
CH3- CH, 0-- CH, CH, +H,0
H (Delhi 2017) Ap) 73. Write the main product(s) in the following reaction:

11.6 Ethers CHa

CH3-C--0-CHg + HI ’
MCQ CH, (1/3, Delhi 2016, 1/2, Al 2016)
65.
Assertion (A): (CH3)3C--0-CHg
(CH3), C--l andICH,OH on
gives
treatment with HI. 74. How is the following conversion carried out?
Sy1 mechanism. Anisole to p-bromoanisole (1/3, Delhi 2015C)
Reason (R):The reaction occurs by
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