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Alcohols Phenols and Ethers question

2019 · 9 Apr · Shift 1 · Q2
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Alcohols Phenols and Ethers question

2019 · 9 Apr · Shift 1 · Q2

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
The major product of the following reaction is : CH3CH=CHCO2CH3→LiAlH4{\rm{C}}{{\rm{H}}_3}{\rm{CH = CHC}}{{\rm{O}}_2}{\rm{CH_3 }}\xrightarrow{LiAl{H_4}}CH3​CH=CHCO2​CH3​LiAlH4​​
  1. A
    CH3CH2CH2CHOCH_3CH_2CH_2CHOCH3​CH2​CH2​CHO
  2. B
    CH3CH2CH2CO2CH3CH_3CH_2CH_2CO_2CH_3CH3​CH2​CH2​CO2​CH3​
  3. C
    CH3CH=CHCH2OHCH_3CH = CHCH_2OHCH3​CH=CHCH2​OH
  4. D
    CH3CH2CH2CH2OHCH_3CH_2CH_2CH_2OHCH3​CH2​CH2​CH2​OH
View written solutionFree

Correct answer: C

  1. Identify the substrate

The given compound is:

CH3CH=CHCO2CH3CH_3CH=CHCO_2CH_3CH3​CH=CHCO2​CH3​

This is an α,β\alpha,\betaα,β-unsaturated ester (methyl crotonate).


  1. Reagent used

The reagent is:

LiAlH4LiAlH_4LiAlH4​

Lithium aluminium hydride is a strong reducing agent.

For esters, LiAlH4LiAlH_4LiAlH4​ reduces the ester group:

RCOOR′→LiAlH4RCH2OH+R′OHRCOOR' \xrightarrow{LiAlH_4} RCH_2OH + R'OHRCOOR′LiAlH4​​RCH2​OH+R′OH

Importantly, under normal conditions, it reduces the ester carbonyl to a primary alcohol, while the isolated or conjugated C=CC=CC=C bond generally remains unchanged.


  1. Apply reduction to the given ester

Starting compound:

CH3CH=CHCO2CH3CH_3CH=CHCO_2CH_3CH3​CH=CHCO2​CH3​

Reduction of the ester part −CO2CH3-CO_2CH_3−CO2​CH3​ gives:

CH3CH=CHCH2OHCH_3CH=CHCH_2OHCH3​CH=CHCH2​OH

The double bond remains as it is.


  1. Check options
  • A: CH3CH2CH2CHOCH_3CH_2CH_2CHOCH3​CH2​CH2​CHO
    This is an aldehyde. LiAlH4LiAlH_4LiAlH4​ does not stop at aldehyde in ester reduction. Incorrect.

  • B: CH3CH2CH2CO2CH3CH_3CH_2CH_2CO_2CH_3CH3​CH2​CH2​CO2​CH3​
    This is a saturated ester, not the reduction product. Incorrect.

  • C: CH3CH=CHCH2OHCH_3CH=CHCH_2OHCH3​CH=CHCH2​OH
    This matches ester reduction with retention of C=CC=CC=C. Correct.

  • D: CH3CH2CH2CH2OHCH_3CH_2CH_2CH_2OHCH3​CH2​CH2​CH2​OH
    This would require reduction of both ester and double bond. LiAlH4LiAlH_4LiAlH4​ does not usually reduce the alkene here. Incorrect.


  1. Final answer

The major product is:

CH3CH=CHCH2OH\boxed{CH_3CH=CHCH_2OH}CH3​CH=CHCH2​OH​

So, the correct option is C.


  1. Comparison with stored correct answer

Stored correct answer: C
Derived answer: C

They agree.

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