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SolutionsReduction

1. Reduction products

Give the product of the NaBH4 reduction of:

  1. Propanal
  2. Cyclohexanone
  3. Acetophenone (C6H5COCH3)
  1. 1-Propanol (primary alcohol).
  2. Cyclohexanol (secondary).
  3. 1-Phenylethanol (secondary).

2. Selectivity

What is obtained when ethyl 4-oxopentanoate, CH3COCH2CH2COOEt, is reduced with NaBH4? And with LiAlH4?

With NaBH4 only the ketone is reduced: CH3CH(OH)CH2CH2COOEt. With LiAlH4 both the ketone and the ester are reduced: CH3CH(OH)CH2CH2CH2OH (1,4-pentanediol).

NaBH4 is more selective: it reduces aldehydes and ketones, but not esters.

3. Oxidation states

What is the oxidation state of the functional carbon in methanol, formaldehyde and formic acid?

Methanol, −2; formaldehyde, 0; formic acid, +2. Going from the acid or the aldehyde to the alcohol is a reduction.

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