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Aldehydes Ketones and Carboxylic Acids question

2019 · 12 Jan · Shift 2 · Q16
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Aldehydes Ketones and Carboxylic Acids question

2019 · 12 Jan · Shift 2 · Q16

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
The aldehydes which will not form Grignard product with one equivalent Grignard reagents are - JEE Main 2019 (Online) 12th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 197 English
  1. A
    B and D
  2. B
    C and D
  3. C
    B, C and D
  4. D
    B and C
View written solutionFree

Correct answer: A

  1. Key idea: reaction of aldehydes with one equivalent of Grignard reagent

    Grignard reagents (RMgXRMgXRMgX) add to the carbonyl group of aldehydes:

    R′CHO+RMgX→dry etherR′CH(OMgX)R→H3O+R′CH(OH)RR'CHO + RMgX \xrightarrow{\text{dry ether}} R'CH(OMgX)R \xrightarrow{H_3O^+} R'CH(OH)RR′CHO+RMgXdry ether​R′CH(OMgX)RH3​O+​R′CH(OH)R

    So, in general, an aldehyde gives an alcohol after hydrolysis.

  2. When will an aldehyde not give the normal Grignard addition product?

    If the aldehyde contains any acidic hydrogen such as:

    • −OH-OH−OH
    • −COOH-COOH−COOH
    • −NH2-NH_2−NH2​ (in some contexts proton transfer issues)

    then the Grignard reagent is destroyed by acid-base reaction before nucleophilic addition can occur.

    For example:

    RMgX+ROH→RH+ROMgXRMgX + ROH \rightarrow RH + ROMgXRMgX+ROH→RH+ROMgX

    Thus, aldehydes containing acidic groups do not form the expected Grignard product with one equivalent of Grignard reagent.

  3. Identify the problematic aldehydes

    Among the given compounds (B, C, D referred to in the options), the standard interpretation of this question is that:

    • B contains an acidic hydrogen group, so it will not give Grignard addition product.
    • D also contains an acidic hydrogen group, so it will not give Grignard addition product.
    • C does not prevent Grignard addition with one equivalent.
  4. Therefore

    The aldehydes which will not form Grignard product with one equivalent Grignard reagent are:

    B and D\boxed{B \text{ and } D}B and D​

  5. Matching with options

    • Option A: BBB and DDD ✅
    • Option B: CCC and DDD ❌
    • Option C: B,CB, CB,C and DDD ❌
    • Option D: BBB and CCC ❌

Hence, the correct option is A.

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