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Aldehydes Ketones and Carboxylic Acids question

2019 · 12 Jan · Shift 1 · Q22
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Aldehydes Ketones and Carboxylic Acids question

2019 · 12 Jan · Shift 1 · Q22

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
In the following reaction :

Aldehyde + Alcohol →HCl\xrightarrow{HCl}HCl​ Acetal

Aldehyde Alcohol
HCHO tBuOH
CH3CHO MeOH

The best combination is
  1. A
    CH3CHOCH_3CHOCH3​CHO and MeOHMeOHMeOH
  2. B
    HCHO and MeOH
  3. C
    CH3CHOCH_3CHOCH3​CHO and tBuOHtBuOHtBuOH
  4. D
    HCHO and tBuOH
View written solutionFree

Correct answer: B

  1. Reaction involved: formation of acetal

An aldehyde reacts with an alcohol in the presence of acid to form first a hemiacetal and then an acetal:

RCHO+2ROH→H+RCH(OR)2+H2ORCHO + 2ROH \xrightarrow{H^+} RCH(OR)_2 + H_2ORCHO+2ROHH+​RCH(OR)2​+H2​O

This reaction is favored when:

  • the aldehyde is more reactive,
  • the alcohol is less hindered,
  • acetal formation is not sterically difficult.

  1. Compare the aldehydes

The two aldehydes are:

  • HCHO\mathrm{HCHO}HCHO (formaldehyde)
  • CH3CHO\mathrm{CH_3CHO}CH3​CHO (acetaldehyde)

Formaldehyde is more reactive than acetaldehyde toward nucleophilic addition because it has:

  • less steric hindrance,
  • no electron-donating alkyl group.

So, for acetal formation:

HCHO>CH3CHO\mathrm{HCHO > CH_3CHO}HCHO>CH3​CHO


  1. Compare the alcohols

The two alcohols are:

  • MeOH\mathrm{MeOH}MeOH (methanol)
  • tBuOH\mathrm{tBuOH}tBuOH (tert-butanol)

Methanol is much better for acetal formation because:

  • it is less hindered,
  • it attacks the carbonyl carbon more easily.

Tert-butanol is highly hindered and under acidic conditions may also undergo side reactions/dehydration, so it is a poor choice for forming acetals.

Thus:

MeOH≫tBuOH\mathrm{MeOH \gg tBuOH}MeOH≫tBuOH


  1. Evaluate the options

Option A: CH3CHO\mathrm{CH_3CHO}CH3​CHO and MeOH\mathrm{MeOH}MeOH

Possible, but acetaldehyde is less reactive than formaldehyde.

Option B: HCHO\mathrm{HCHO}HCHO and MeOH\mathrm{MeOH}MeOH

This is the best combination because:

  • HCHO\mathrm{HCHO}HCHO is the most reactive aldehyde,
  • MeOH\mathrm{MeOH}MeOH is the least hindered alcohol.

Option C: CH3CHO\mathrm{CH_3CHO}CH3​CHO and tBuOH\mathrm{tBuOH}tBuOH

Both components are less favorable; especially tBuOH\mathrm{tBuOH}tBuOH is very poor for acetal formation.

Option D: HCHO\mathrm{HCHO}HCHO and tBuOH\mathrm{tBuOH}tBuOH

Formaldehyde is good, but tBuOH\mathrm{tBuOH}tBuOH is highly hindered, so this is inferior to option B.


  1. Conclusion

The best aldehyde–alcohol pair for acetal formation is:

HCHO and MeOH\boxed{\mathrm{HCHO \ and \ MeOH}}HCHO and MeOH​

So the correct option is B.

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