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Question 55

The major product obtained in the following reaction is:

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Lithium aluminum hydride ($$\text{LiAlH}_4$$) is an exceptionally powerful, non-selective reducing agent. When used in excess, it reduces a wide variety of carbonyl-containing and nitrogenous functional groups:

  • Carboxylic Acid ($$-\text{COOH}$$): Reduced completely down to a primary alcohol ($$-\text{CH}_2\text{OH}$$).
  • Ketone ($$-\text{C}=\text{O}$$): Reduced down to a secondary alcohol ($$-\text{CH(OH)}--$$).
  • Nitro Group ($$-\text{NO}_2$$): When attached to an aliphatic (non-aromatic) carbon ring template, it is reduced cleanly to a primary amine ($$-\text{NH}_2$$).
  • Isolated Carbon-Carbon Double Bond ($$\text{C}=\text{C}$$) or Triple Bond ($$\text{C}\equiv\text{C}$$): Generally, isolated alkenes and alkynes are inert to $$\text{LiAlH}_4$$ because they lack an electrophilic center for a hydride ion ($$\text{H}^-$$) to attack.


  • 1. Carboxylic Acid Conversion:

    $$\text{--COOH} \xrightarrow{\text{LiAlH}_4 \text{ (excess)}} \text{--CH}_2\text{OH}$$

    The top carboxylic acid group is transformed into a primary hydroxymethyl substituent.


  • 2. Aliphatic Nitro Conversion:

    $$\text{--NO}_2 \xrightarrow{\text{LiAlH}_4 \text{ (excess)}} \text{--NH}_2$$

    The nitro group attached to the bottom-left of the cyclohexane ring is reduced to an amino group.


  • 3. Ketone Conversion:

    $$\text{--C}(=\text{O})\text{CH}_3 \xrightarrow{\text{LiAlH}_4 \text{ (excess)}} \text{--CH}(\text{OH})\text{CH}_3$$

    The acetyl/ketone side chain at the bottom-right is reduced to a secondary alcohol.


  • 4. Isolated Alkene Behaviour:

    The isolated carbon-carbon double bond shown in the upper right arm of the ring lacks any strong electron-withdrawing conjugation. As a result, it remains completely untouched by the hydride reduction mechanism.

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