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Alcohols, Phenols and Ethers · Question 43

AIPMT 2007MCQMedium📈 Topic in 12% papers+4−1
1

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

Answer

(3) CH3- CH3 |CH-CH2OH + CH3CH2I

Solution

As per NCERT, in the cleavage of a mixed ether (both groups primary/secondary) by HI, the oxygen is first protonated and then I- attacks the less hindered alkyl group by SN2 mechanism.

Here the two groups are isobutyl (–CH2CH(CH3)2, branched) and ethyl (–CH2CH3).

⇒ Ethyl is less hindered, so I- attacks the ethyl carbon:

CH3- CH3 |CH-CH2-O-CH2-CH3 + HI heated

CH3- CH3 |CH-CH2OH + CH3CH2I

∴ 2-Methylpropan-1-ol and iodoethane are formed.

Answer: (3)

AIPMT 2007

Keep practising — Alcohols, Phenols and Ethers

2

Ethylene oxide when treated with Grignard reagent yields

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

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
4

Which one of the following compounds is most acidic?

  1. Cl-CH2-CH2-OH
  2. [figure]
  3. [figure]
  4. [figure]
AIPMT 2005
5

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
6

Which one of the following will not form a yellow precipitate on heating with an alkaline solution of iodine?

  1. CH3CH(OH)CH3
  2. CH3CH2CH(OH)CH3
  3. CH3OH
  4. CH3CH2OH
AIPMT 2004
7

Which one of the following can be oxidised to the corresponding carbonyl compound?

  1. 2-Hydroxypropane
  2. ortho-Nitrophenol
  3. Phenol
  4. 2-Methyl-2-hydroxypropane
AIPMT 2004
8

In a set of the given reactions, acetic acid yielded a product C. CH3COOH + PCl5 A [Anh. AlCl3]C6H6 B [ether]C2H5MgBr C Product C would be

  1. CH3CH(OH)C2H5
  2. CH3COC6H5
  3. CH3CH(OH)C6H5
  4. CH3- C2H5 |C(OH)C6H5
AIPMT 2003
9

n-Propyl alcohol and isopropyl alcohol can be chemically distinguished by which reagent?

  1. PCl5
  2. reduction
  3. oxidation with potassium dichromate
  4. ozonolysis
AIPMT 2002
10

When phenol is treated with CHCl3 and NaOH, the product formed is

  1. benzaldehyde
  2. salicylaldehyde
  3. salicylic acid
  4. benzoic acid
AIPMT 2002
11

In preparation of alkene from alcohol using Al2O3 which is the effective factor ?

  1. Porosity of Al2O3
  2. Temperature
  3. Concentration
  4. Surface area of Al2O3
AIPMT 2001

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