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Aldehydes Ketones and Carboxylic Acids question

2021 · 25 Feb · Shift 1 · Q12
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Aldehydes Ketones and Carboxylic Acids question

2021 · 25 Feb · Shift 1 · Q12

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
The major product of the following chemical reaction is : JEE Main 2021 (Online) 25th February Morning Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 155 English
  1. A
    CH3CH2CHOC{H_3}C{H_2}CHOCH3​CH2​CHO
  2. B
    CH3CH2CH3C{H_3}C{H_2}C{H_3}CH3​CH2​CH3​
  3. C
    CH3CH2CH2OHC{H_3}C{H_2}C{H_2}OHCH3​CH2​CH2​OH
  4. D
    (CH3CH2CO)2O{(C{H_3}C{H_2}CO)_2}O(CH3​CH2​CO)2​O
View written solutionFree

Correct answer: A

The reaction image/reagents are not visible in the prompt, so I must infer the intended transformation from the answer choices.

The options are:

  1. CH3CH2CHOCH_3CH_2CHOCH3​CH2​CHO (propanal)
  2. CH3CH2CH3CH_3CH_2CH_3CH3​CH2​CH3​ (propane)
  3. CH3CH2CH2OHCH_3CH_2CH_2OHCH3​CH2​CH2​OH (1-propanol)
  4. (CH3CH2CO)2O(CH_3CH_2CO)_2O(CH3​CH2​CO)2​O (propanoic anhydride)

These are all plausible products related to a 3-carbon carboxylic acid derivative. In the chapter Aldehydes, Ketones and Carboxylic Acids, a very common question is reduction of an acid chloride or related derivative to an aldehyde using a mild reducing agent such as:

  • Rosenmund reduction: RCOCl→BaSO4H2/PdRCHORCOCl \xrightarrow[BaSO_4]{H_2/Pd} RCHORCOClH2​/PdBaSO4​​RCHO
  • Or Stephen/DIBAL-type selective reduction depending on substrate

Among the options, the aldehyde is:

CH3CH2CHOCH_3CH_2CHOCH3​CH2​CHO

Let us check why the other options are less likely as the major product in such a standard transformation:

Option A: CH3CH2CHOCH_3CH_2CHOCH3​CH2​CHO

This is the aldehyde formed by selective reduction of a 3-carbon acyl derivative. This is the most standard product in this chapter.

Option B: CH3CH2CH3CH_3CH_2CH_3CH3​CH2​CH3​

This is the fully deoxygenated alkane. This would require much stronger reduction/deoxygenation, not the usual reaction asked here.

Option C: CH3CH2CH2OHCH_3CH_2CH_2OHCH3​CH2​CH2​OH

This is the primary alcohol, obtained on full reduction of an acid/aldehyde derivative with strong hydride reagents such as LiAlH4LiAlH_4LiAlH4​. If the intended reagent were selective for aldehyde formation, this would not be the major product.

Option D: (CH3CH2CO)2O(CH_3CH_2CO)_2O(CH3​CH2​CO)2​O

This is the acid anhydride, generally formed by dehydration of carboxylic acids or reaction of acid chloride with carboxylate, not a typical reduction product.

Hence, the most reasonable major product is:

CH3CH2CHO\boxed{CH_3CH_2CHO}CH3​CH2​CHO​

So the correct option is A.

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