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    Alcohol, Phenol 7 Ether CHEMHACK

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    Rajendera Sen

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    Alcohol, Phenol 7 Ether CHEMHACK

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    Alcohol, Phenol 7 Ether CHEMHACK

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    Rajendera Sen

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    Chapter 5

    ALCOHOLS, PHENOLS
    AND ETHERS
    INTRODUCTION
    1. Allylic and benzylic alcohols may be primary, secondary or tertiary. T/F
    2. Draw sec-Butyl alcohol.
    3. Common name of is -

    4. Draw isobutyl alcohol.


    5. For naming polyhydric alcohols, the ‘e’ of alkane is replaced by ‘ol’. T/F
    6. Draw ortho-cresol.
    7. Common name of - (i) (ii) (iii)

    8. Draw Anisole. (NEET)


    9. Draw Phenetole.
    10. Common name of -

    11. IUPAC name of - (i) (iii)

    (ii) (iv)

    12. The bond angle in alcohols is slightly more than the tetrahedral angle. T/F
    13. Bond angle in ether is slightly higher than alcohol because -

    ALCOHOLS AND PHENOLS


    PREPARATION OF ALCOHOLS
    14.

    15.

    ANSWERS 1
    32 CHEMHACK

    16. _____ on reaction with B₂H₆ give trialkyl boranes.


    17. Syn/Anti addition takes place in B₂H₆.
    18. Hydroboration oxidation rxn follow markovnikov/anti-markovnikov rule.
    19. Ring expansion and rearrangement takes place in HBO (Hydroboration-oxidation). T/F
    20. CH₃-CH=CH₂ + (BH₃)₂ H₂O/OH⁻
    21. CH₃-CO-CH=CH₂ + (BH₃)₂ H₂O/OH⁻
    22. Reagents used in Oxymercuration demercuration (OMDM) rxn are - (2)
    23. Syn/anti addition takes place in OMDM.
    24. No ring expansion and rearrangement takes place in OMDM. T/F
    25. CH₃-CH=CH₂ + H₂O Hg(CH₃COO)₂/NaBH₄

    26.

    27.

    28.

    29. RCHO + H₂/Pd → (JEE)


    30. RCOR’ + NaBH₄/H₂O →
    31. Esters, carboxylic acids and acid chloride are only reduced by LiAlH₄/NaBH₄.
    32. LiAlH₄ and NaBH₄ do not reduce C=C. T/F
    33. Reducing agents which reduce = bond are - (4)
    34. Ester LiAlH₄/H₃O⁺
    35. CH₃CHO LiAlD₄/H₃O⁺
    36. CH₃CHO LiAlH₄/D₃O⁺
    37. Commercially acids are converted to alcohol by -
    38. R-CO-R + R’-MgX after hydrolysis give -
    39. Ester on rxn with Grignard reagent produces 1°/2°/3° alcohol.

    PREPARATION OF PHENOLS

    40. Phenol is also known as -


    41. A + NaOH 623K/300atm B, B on acidification → Phenol, Identify A & B. (JEE 2021)
    42. A
    B

    ANSWERS 1 ANSWERS 2
    ALCOHOLS, PHENOLS AND ETHERS 33

    43. A B

    44. Draw cumene.

    45. A B (NEET)

    46. (NEET 2021)

    PHYSICAL AND CHEMICAL PROPERTIES

    47. The solubility of alcohol decreases with increase in size of the alkyl/aryl group. T/F
    48. Phenol is more acidic than alcohol. T/F
    49. Water is more acidic than methanol. T/F
    50. Phenol is a stronger acid than water. T/F
    51. Phenol molecules are more stable than phenoxide ions. T/F
    52. Arrange o-nitrophenol, p-nitrophenol, m--nitrophenol in order of acidic strength.
    53. Arrange o-fluorophenol, p-fluorophenol, m-fluorophenol in order of acidic strength.
    54. Arrange o-cresol, p-cresol and m-cresol in order of acidic strength.
    55. Arrange o-methoxyphenol, p-methoxyphenol and m-methoxyphenol in order of acidic strength.

    CHEMICAL REACTION OF ALCOHOL

    56. ROH + Na →
    57.

    58. The reaction with acid chloride is carried out in the presence of a _______ so as to neutralise HCl which is
    formed during the reaction.

    59.

    60. Arrange Cl⁻, OH⁻, RO⁻ and R-CO-O⁻ in order of their leaving tendency.
    61. Lucas reagent is - (NEET) (JEE)
    62. Lucas test is a test to find -
    ANSWERS 2
    34 CHEMHACK

    63. How does Lucas reagent differentiate between 1°, 2°, 3° alcohol? (NEET)
    64. How does Lucas reagent cause turbidity ?
    65. Order of 1°, 2°, 3° alcohol in its ease of dehydration is - (JEE)
    66. Dehydration of alcohol happens by treating it with - (5)

    67.

    68. RCH₂OH (in presence of acidified KMnO₄) → (JEE)


    69. RCH₂OH (in presence of CrO₃) → (JEE)
    70. CH₃-CH=CH-CH₂OH (in presence of PCC) → (JEE)
    71. Sec-alcohols are oxidised to _____ in CrO₃.
    72. RCH₂OH Cu/573K
    73. R-CH(OH)-R’ Cu/573K (NEET) (JEE 2021)
    74. ?

    75.

    76. MnO₂ oxidises only allylic or benzylic alcohol. T/F

    CHEMICAL REACTIONS OF PHENOL


    77. Ortho and para nitrophenol can be separated by ______ technique. (NEET) (JEE)
    78. p-nitrophenol has intra/intermolecular H bonding.
    79. Direct nitration of phenol by conc. HNO₃ gives poor yields of picric acid. T/F (JEE)
    80. To get good yields of picric acid, what is done? (JEE)

    81. Major and minor products formed are -

    82. Phenol + Br₂/H₂O → A. Identify A and also its colour. (JEE)


    83. A B (JEE)

    84. Reagents in Reimer-Tiemann reaction are -

    85. (NEET) (JEE)

    86. Intermediate electrophile formed in Rimer-tiemann reaction that attack benzene is - (NEET) (JEE)

    ANSWERS 2 ANSWERS 3
    ALCOHOLS, PHENOLS AND ETHERS 35

    87.

    88.

    89.

    SOME COMMERCIALLY IMPORTANT ALCOHOLS


    90. Methanol is also known as -
    91.

    →
    92. C₁₂H₂₂O₁₁ + H₂O Glucose + Fructose, enzyme used in this rxn - (JEE 2021)
    →
    93. Glucose C₂H₅OH + CO₂, enzyme used in this rxn -
    94. Action of zymase is inhibited once the % of alcohol formed reaches ___%.
    95. Commercial alcohol is made unfit for drinking by mixing - (2)
    96. The above process is called -

    ETHERS
    PREPARATION OF ETHERS

    97. CH₃CH₂OH H₂SO₄/443K


    98. Alcohol in low temp. conditions form ether. T/F
    99. Ether formation is a Sn1/Sn2 reaction.
    100. Write Williamson synthesis reaction - (NEET)
    101. If 3° alkoxide ion is used, no ether is formed. T/F
    102. If 3° alkyl halide is used, no ether is formed. T/F
    103. The B.P. of alcohol is less than ether for the same molar mass. T/F

    CHEMICAL REACTIONS
    104. Least reactive functional group is -
    105. Aryl-oxygen bond is more stable than alkyl-oxygen bond. T/F
    106. The order of reactivity of hydrogen halides with ether is -
    107. CH₃-O-CH₂-CH₃ + HI →
    ANSWERS 3
    36 CHEMHACK

    108. If a tertiary alkyl group is present in the ether, the reaction process through ____ mechanism, otherwise it
    proceed through ____

    109.

    110.

    111.

    112. Victor meyer test is not given by 1°/ 2°/ 3° alcohol. (NEET)
    113. Aspirin is acetylation product of - (NEET)
    114. Oil of winter green is - (NEET)

    ANSWERS 3
    ALCOHOLS, PHENOLS AND ETHERS 37

    ANSWERS
    20. CH₃-CH₂-CH₂-OH
    • INTRODUCTION
    1. T 21. CH₃-CO-CH(OH)-CH₃, this product is formed
    2. because the terminal carbon have partial +ve charge
    due to resonance with C=O
    3. Isopropyl alcohol 22. Hg(CH₃COO)₂/NaBH₄
    4. 23. Anti
    24. T
    5. F 25. CH₃-CH(OH)-CH₃

    6. 26.

    7. Catechol, resorcinol, hydroquinone or quinol 27.

    8. 9. 28.

    10. Phenyl Isopentyl ether 29. R-CH₂-OH


    11. (i) 2-Ethoxy-1,1-dimethylcyclohexane 30. R-CH(OH)-R’
    (ii) 1-Ethoxy-2-nitrocyclohexane 31. LiAlH₄
    (iii) 4-Chloro-3-ethyl-2-(1-methylethyl)-butan-1-ol 32. T
    (iv) Hex-1-en-3-ol 33. Pd/H₂, B₂H₆, Na/Ethanol, Raney Ni/H₂
    12. F 34. Alcohol
    13. Of repulsion between bulky alkyl groups on either 35. CH₃-CH(OH)-D
    side of O 36. CH₃-CH₂-OD
    • ALCOHOLS AND PHENOLS 37. By converting them to esters followed by
    14. reduction using H₂/Pd (or any other metal)

    15. 38.

    16. Alkene
    17. Syn
    18. Anti-markovnikov rule
    19. F 39. 3°
    40. Carbolic acid
    QUESTIONS 1 QUESTIONS 2
    38 CHEMHACK

    60. Cl⁻ > R-CO-O⁻ > OH⁻ > RO⁻


    41. A - B- [Tip - Strong acid have good leaving conjugate base. As
    HCl > RCOOH > H₂O > ROH in terms of acidity, their
    42. A - Oleum, B - Phenol conjugate base stability order is also the same and
    hence the leaving tendency]
    43. A - B- 61. ZnCl₂/HCl
    62. the 'degree' of alcohol, i.e. 1°, 2°, 3°
    63. 1° alcohol - No turbidity, 2° alcohol - Turbidity after
    44. 5 min, 3° alcohol - turbidity immediate
    →
    64. R-OH + Lucas reagent R-X, which in insoluble in
    Lucas reagent hence give turbidity
    65. 3° > 2° > 1°
    45. A - B - CH₃COCH₃ 66. Protic acid (conc. H₂SO₄ or H₃PO₄), P₂O₅/Δ,
    Al₂O₃/Δ, ZnCl₂, POCl₃/Pyridine

    46. 67. This is pinacole pinacolone


    rearrangement reaction
    47. T 68. R-COOH
    48. T 69. RCHO
    49. F 70. CH₃-CH=CH-CHO
    50. T 71. Ketone
    51. F 72. RCHO
    52. p-nitrophenol > o-nitrophenol > m--nitrophenol 73. R-CO-R’
    53. o > p > m
    54. m > p > o 74.
    55. m > o > p
    56. R-O-Na 75.

    57. 76. T
    77. Steam distillation
    58. base(pyridine) 78. Intermolecular H bonding
    59. 79. T
    80. First phenol is sulphonated than nitrated

    QUESTIONS 2 QUESTIONS 3 QUESTIONS 4


    ALCOHOLS, PHENOLS AND ETHERS 39
    smelling liquid)
    81. 96. Denaturation of alcohol
    Minor Major • ETHERS
    97. CH₂=CH₂
    98. T
    82. white precipitate 99. Sn2
    →
    100. R-X + R-O-Na⁺ R-O-R’ + NaX
    101. F
    83. A - B- 102. T
    103. F
    104. Ether
    84. CHCl₃ + aq NaOH 105. T
    106. HI > HBr > HCl
    85. 107. CH₃-I, CH₃-CH₂-OH
    108. Sn1, Sn2
    86. :CCl₂ (dichlorocarbene)
    109.
    87.

    110.
    88.

    111.
    89.

    90. Wood spirit 112. 3° [Victor mayer give red colour with 1°, blue colour
    91. CH₃OH with 2° and remains colourless with 3° alcohol as no
    92. Invertase reaction with HNO₂ occur]
    93. Zymase 113. Salicylic acid
    94. 14 114. Methyl salicylate
    95. CuSO₄ (to give it a colour) and pyridine (a foul

    QUESTIONS 4 QUESTIONS 5 QUESTIONS 6

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