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All questions of Alcohols, Phenols and Ethers for NEET Exam

Which of the following compounds will form hydrocarbon on reaction with Grignard reagent ?
  • a)
    CH2CHO
  • b)
    CH3COCH3
  • c)
     
     CH3CH2OH
  • d)
    CH3CO2CH3
Correct answer is option 'C'. Can you explain this answer?

Chirag Joshi answered
Formation of Hydrocarbon from Grignard Reagent

Grignard reagent is a very strong nucleophile and a powerful reducing agent. It reacts with various types of carbonyl compounds to form alcohols, which can further react to form hydrocarbons. However, not all carbonyl compounds can form hydrocarbons on reaction with Grignard reagent. Let's discuss the given options:

a) CH2CHO: This is formaldehyde, which has a carbonyl group. It can react with Grignard reagent to form a primary alcohol, but it cannot form a hydrocarbon.

b) CH3COCH3: This is acetone, which also has a carbonyl group. It can react with Grignard reagent to form a secondary alcohol, but it cannot form a hydrocarbon.

c) CH3CH2OH: This is ethanol, which has a hydroxyl group. It can react with Grignard reagent to form a secondary alcohol, which can further react to form an alkene (hydrocarbon).

d) CH3CO2CH3: This is ethyl acetate, which has an ester group. It can react with Grignard reagent to form a tertiary alcohol, but it cannot form a hydrocarbon.

Therefore, the correct answer is option 'C' (CH3CH2OH).

Which one of the following compounds will be most readily attacked by an electrophile ?[1989]
  • a)
    Chlorobenzene
  • b)
    Benzene
  • c)
    Phenol
  • d)
    Toluene
Correct answer is option 'C'. Can you explain this answer?

Abhijeet Goyal answered
Due to strong electron-donating effect of the OH group, the electron density in phenol is much higher than that in toluene, benzene and chlorobenzene and hence phenol is readily attacked by the electrophile.

The stablest among the following is [1994]
  • a)
    CH3CH(OH)2
  • b)
    ClCH2CH(OH)2
  • c)
    (CH3)2 C (OH)2
  • d)
    CCl3 CH (OH)2.
Correct answer is option 'D'. Can you explain this answer?

Soumya Ahuja answered
Due to –I-effect of the three C–Cl-bonding between CI and C-atom of the OH group, CCl3 CH (OH)2 is most stable.

The compound which reacts fastest with Lucas reagent at room temperature is [1989]
  • a)
    Butan-1-ol
  • b)
    Butan-2-ol
  • c)
    2-Methyl propan-1-ol
  • d)
    2-Methylpropan-2-ol
Correct answer is option 'D'. Can you explain this answer?

Maya Sengupta answered
The rates of reaction with lucas reagen t follows the order. 3° alcohol > 2° alcohol > 1° alcohol since carbocations are formed as intermediate, more stable the carbocation, higher will be the reactivity of the parent compound (alcohol). 2-Methylpropan-2-ol generates a 3º carbocation, so it will react fastest; other three generates either 1º or 2º carbocations.
2-Methyl-2-propanol

HBr reacts fastest with 
  • a)
    2-Mehtylpropan-1-ol
  • b)
    2-Methylpropan-2-ol
  • c)
    propan-2-ol
  • d)
    propan-1-ol.
Correct answer is option 'B'. Can you explain this answer?

Roshni Desai answered
Greater the stability of the intermediate carbocation, more reactive is the alcohol.
Since 2-methylpropan-2-ol generates 3° carbocation, therefore, it reacts fastest with HBr.

Increasing order of acid strength among p-methoxyphenol, p-methylphenol and p-nitrophenol is [1993]
  • a)
    p-Nitrophenol, p-Methoxyphenol, p-Methylphenol
  • b)
    p-Methylphenol, p-Methoxyphenol, p-Nitrophenol
  • c)
    p-Nitrophenol, p-Methylphenol, p-Methoxyphenol.
  • d)
    p-Methoxyphenol, p-Methylphenol, p-Nitrophenol
Correct answer is option 'D'. Can you explain this answer?

Vaibhav Basu answered
Electron-donating groups (– OCH3, – CH3 etc.) tend to decrease and electron withdrawing groups (– NO2, – OCH3 etc.) tend to increase the acidic character of phenols. Since – OCH3 is a more powerful electron-donating group than – CH3 group, therefore, p-methylphenol is slightly more acidic than p-methoxyphenol while pnitrophenol is the strongest acid. Thus, option (d), i.e. p-methoxyphenol, pmethylphenol, p-nitrophenol is correct.

1-Phenylethanol can be prepared by the reaction of benzaldehyde with [1997]
  • a)
    ethyl iodide and magnesium
  • b)
    methyl iodide and magnesium
  • c)
    methyl bromide and aluminium bromide
  • d)
    methyl bromide
Correct answer is option 'B'. Can you explain this answer?

Dev Kumar answered
CH3I + Mg----> CH3MgI (organometallic synthesis) now carbonyl group on benzaldehyde undergoes mesomeric effect and develops positive charge on carbonyl carbon and negative charge on oxygen atom. thereafter CH3- attacks on carbonyl carbon and MgI+ attacks on carbonyl oxygen. hydrolysis is followed and 1-Phenylethanol is formed.

Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated HI? [NEET 2013]
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'B'. Can you explain this answer?

Shounak Nair answered
The reaction will proceed via SN1 or SN2 based on nature of alkyl group. If alkyl group attached is 3°. The reaction will proceed through the SN1 mechanism and if alkyl group is primary reaction will proceed through SN2 mechanism.
                                                  

Which one of the following compounds has the most acidic nature? [2010]
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'B'. Can you explain this answer?

Ritika Khanna answered
Phenolis most acidic because its conjugate base is stabilised due to resonance, while the rest three compounds are alcohols, hence, their corrosponding conjugate bases do not exhibit resonance

H2COH · CH2OH on heating with periodic acid gives:           [2009]
  • a)
    2 HCOOH
  • b)
  • c)
  • d)
    2 CO2
Correct answer is option 'C'. Can you explain this answer?

Naveen Menon answered
1, 2 – Diols, when treated with an aqueous solution of periodic acid give aldehyde or ketones
Note that a 1° alcohol gives CH2O. Since in glycol both the OH groups, are primary hence give 2 molecules of CH2O as by product.

The major organic product in the reaction, CH3 — O — CH(CH3)2 + HI → Product is  [2006]
  • a)
    ICH2OCH(CH3)2
  • b)
  • c)
    CH3I + (CH3)2CHOH
  • d)
    CH3OH + (CH3)2CHI
Correct answer is option 'C'. Can you explain this answer?

Lead Academy answered
First HI will break into H+ and I-. Then H+ attacks on ether to form CH3O+HCH(CH3)2
Being an excellent nucleophile, I- attacks where it is easy to attack and so it will go for less bulky CH3 to form CH3I and (CH3)2CHOH.

The ionization constant of phenol is higher than that of ethanol because : [2000]
  • a)
    phenoxide ion is bulkier than ethoxide
  • b)
    phenoxide ion is stronger base than ethoxide
  • c)
    ph en oxide ion is st abilized t h r ough delocalization
  • d)
    phenoxide ion is less stable than ethoxide
Correct answer is option 'C'. Can you explain this answer?

Naveen Menon answered
The acidic nature of phenol is due to the formation of stable phenoxide ion in solution
The phenoxide ion is stable due to resonance.
The negative charge is delocalized in the benzene ring which is a stabilizing factor in the phenoxide ion and increase acidity of phenol. wheras no resonance is possible in alkoxide ions (RO)derived from alcohol. The negative charge is localized on oxygen atom.
Thus, alcohols are not acidic.

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