Question

Difficulty: MediumAlkanals and Alkanones: Oxidation, Reduction, and Distinction Tests

Which of the following carbonyl compounds yields a secondary alcohol upon reduction with lithium tetrahydridoaluminate(III) (LiAlH4LiAlH_4)?

  1. PropanoneAnswer
  2. B
    Ethanal
  3. C
    Butanal
  4. D
    Methanal

Answer

Propanone yields a secondary alcohol (propan-2-ol) when reduced by lithium tetrahydridoaluminate(III).
Propanone is a ketone (alkanone). When reduced with lithium tetrahydridoaluminate(III) (LiAlH4LiAlH_4), the carbonyl carbon (C=OC=O) is converted to a secondary alcohol group (CH(OH)-CH(OH)-). Specifically, propanone (CH3COCH3CH_3COCH_3) is reduced to propan-2-ol (CH3CH(OH)CH3CH_3CH(OH)CH_3), which contains a carbon atom bonded to two other carbon atoms and the hydroxyl group.

Step-by-Step Solution

1
Identify the functional groups of the given carbonyl compounds.
Propanone (CH3COCH3CH_3COCH_3) is a ketone (alkanone), whereas ethanal (CH3CHOCH_3CHO), butanal (CH3CH2CH2CHOCH_3CH_2CH_2CHO), and methanal (HCHOHCHO) are aldehydes (alkanals).
Alkanals and alkanones exhibit distinct reduction behaviors based on the position of the carbonyl group (C=OC=O).
2
Apply the general reduction reaction rules for alkanals and alkanones using LiAlH4LiAlH_4.
Reduction of an alkanal (RCHOR-CHO) produces a primary alcohol (RCH2OHR-CH_2OH). Reduction of an alkanone (RCORR-CO-R') produces a secondary alcohol (RCH(OH)RR-CH(OH)-R').
The hydride ion (HH^-) adds to the carbonyl carbon atom, converting the ketone group into a secondary hydroxyl group.
3
Determine which compound forms a secondary alcohol.
Propanone (CH3COCH3CH_3COCH_3) is reduced to propan-2-ol (CH3CH(OH)CH3CH_3CH(OH)CH_3), which is a secondary alcohol.
Propan-2-ol has the hydroxyl-bearing carbon attached to two other carbon atoms, fitting the definition of a secondary alcohol.

Key Concept

Reduction of Alkanals and Alkanones
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