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Alcohols, Phenols and Ethers

AIPMT 2010 (Prelims)MCQEasy📈 Topic in 25% papers+4−1
Ques. 1AIPMT 2010 (Prelims)

Given are cyclohexanol (I), acetic acid (II), 2, 4, 6-trinitrophenol (III) and phenol (IV). In these the order of decreasing acidic character will be

  1. III > II > IV > I
  2. II > III > I > IV
  3. II > III > IV > I
  4. III > IV > II > I

Answer

(1) III > II > IV > I

Solution

2,4,6-Trinitrophenol (picric acid): three –NO2 groups strongly stabilise the phenoxide ion (pKa 0.7) – strongest acid.

Acetic acid (pKa 4.76): carboxylate ion stabilised by two equivalent resonance structures.

Phenol (pKa 10): phenoxide is resonance stabilised, but less effectively.

Cyclohexanol (pKa 18): alkoxide ion is not resonance stabilised – weakest acid.

III > II > IV > I

Answer: (1)

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Ques. 2AIPMT 2010 (Prelims)

Among the following four compounds (i) Phenol (ii) Methyl phenol (iii) Meta-nitrophenol (iv) Para-nitrophenol The acidity order is

  1. (iv) > (iii) > (i) > (ii)
  2. (iii) > (iv) > (i) > (ii)
  3. (i) > (iv) > (iii) > (ii)
  4. (ii) > (i) > (iii) > (iv)
Ques. 3AIPMT 2010 (Prelims)

Which of the following compounds has the most acidic nature?

  1. [figure]
  2. [figure]
  3. [figure]
  4. [figure]
Ques. 4AIPMT 2009

Consider the following reaction : Phenol Zn dust X [Anhyd. AlCl3]CH3Cl Y Alkaline KMnO4 Z the product Z is

  1. benzaldehyde
  2. benzoic acid
  3. benzene
  4. toluene
Ques. 5AIPMT 2009

HOCH2CH2OH on heating with periodic acid gives

  1. 2HCOOH
  2. [figure]
  3. [figure]
  4. 2CO2
Ques. 6AIPMT 2009

Consider the following reaction : Ethanol PBr3 X alc. KOH Y [(ii) H2O, heat](i) H2SO4, room temperature Z the product Z is

  1. CH3CH2-O-CH2-CH3
  2. CH3-CH2-O-SO3H
  3. CH3CH2OH
  4. CH2=CH2
Ques. 7AIPMT 2007

In the reaction : CH3- CH3 |CH-CH2-O-CH2-CH3 + HI heated Which of the following compounds will be formed?

  1. CH3- CH3 |CH-CH3 + CH3CH2OH
  2. CH3- CH3 |CH-CH2OH + CH3CH3
  3. CH3- CH3 |CH-CH2OH + CH3CH2I
  4. CH3- CH3 |CH-CH2-I + CH3CH2OH
Ques. 8AIPMT 2006

Ethylene oxide when treated with Grignard reagent yields

  1. primary alcohol
  2. secondary alcohol
  3. tertiary alcohol
  4. cyclopropyl alcohol
Ques. 9AIPMT 2006

The major organic product in the reaction is CH3-O-CH(CH3)2 + HI products

  1. CH3I + (CH3)2CHOH
  2. CH3OH + (CH3)2CHI
  3. ICH2OCH(CH3)2
  4. CH3O I |C(CH3)2
Ques. 10AIPMT 2005

Which one of the following compounds is most acidic?

  1. Cl-CH2-CH2-OH
  2. [figure]
  3. [figure]
  4. [figure]
Ques. 11AIPMT 2004

The -OH group of an alcohol or the -COOH group of a carboxylic acid can be replaced by -Cl using

  1. phosphorus pentachloride
  2. hypochlorous acid
  3. chlorine
  4. hydrochloric acid

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