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Alcohols, Phenols and Ethers · Question 37

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

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)

AIPMT 2010 (Prelims)

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2

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)
AIPMT 2010 (Prelims)
3

Which of the following compounds has the most acidic nature?

  1. [figure]
  2. [figure]
  3. [figure]
  4. [figure]
AIPMT 2010 (Prelims)
4

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
AIPMT 2009
5

HOCH2CH2OH on heating with periodic acid gives

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

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
AIPMT 2009
7

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
AIPMT 2007
8

Ethylene oxide when treated with Grignard reagent yields

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

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
AIPMT 2006
10

Which one of the following compounds is most acidic?

  1. Cl-CH2-CH2-OH
  2. [figure]
  3. [figure]
  4. [figure]
AIPMT 2005
11

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
AIPMT 2004

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